If you just had the discipline to work longer hours, you’d earn more.

It’s compelling because it feels fair—if someone works harder, they should achieve more.

We buy into this “meritocracy messaging”: that if we want to achieve great things or experience success, it has to feel like work. A healthy body, an overflowing bank account, an amazing job…surely these aspects of Adulting Porn are only available to those with the self-control and work ethic to arduously strive for them, right?

But successful people are not more disciplined—they’ve just found approaches they enjoy.

Take exercise and healthy eating, for example: I don’t enjoy wandering around a big box gym, poking at a few smelly machines, and indiscriminately curling dumbbells. So guess what? I don’t. If my only option for exercise were this hypothetical poorly lit big box gym with bad ’80s music and zero structure, I’d probably never exercise. 

At my most fit, I was going to 7–9 fitness classes per week. I loved the format of the classes, I loved the music, I loved the instructors—I thoroughly enjoyed my time in these classes, even if we were doing four straight minutes of burpees at 5:45am.

It wasn’t discipline that pulled me forward—it was joy. As soon as it became genuinely enjoyable, it was easy to work out. It actually required very little discipline.

This is the secret that productivity experts already know: It’s why they encourage “getting into flow state,” the magical, psychological zone wherein time collapses, the work becomes fun, and you derive a deep sense of satisfaction from whatever you’re doing.

So often we assume it’s the person who, regardless of the environment, determines the outcomes. We don’t give our environment enough credit.

But it’s easy to make good decisions when the good decisions feel good. Rather than trying to change yourself, try changing your environment instead.

Hard work ≠ guaranteed higher income

Similarly, working really hard doesn’t guarantee you’re going to make a lot of money. 

Most low-wage workers are busting their asses. People with money are often no harder working than those without it. But the paradoxical relationship between work that feels “easy” and the amount of money I earn used to confuse me: How is it that I enjoy what I do more and earn more now? 

This two-hour-long interview with MrBeast encapsulates it well: MrBeast, aka Jimmy Donaldson, has been making YouTube videos since he was a kid, raking in more than 24 billion views on his channel and 100+ million subscribers. When he’s asked how he’s achieved so much by age 25, he has a simple answer: He’s obsessed with it. Working on videos for 18 hours a day is what he wants to do. 

The idea that you have to be intensely exerting yourself or displaying herculean feats of discipline day after day to achieve outstanding results is perhaps the biggest con of all. The best results usually come from the things that make us forget to eat because we’re so engrossed. It takes more effort to pull ourselves away than to keep going.

This is why it’s crucial to pursue alignment in your life (and work, and health, and all the other things that impact your quality of life).

When the things you’re doing (your habits, your thought patterns, etc.) are in alignment with the essence of who you are, how you learn, and what you’re good at, successful results follow naturally. No need to strong-arm or force yourself to do the things you think you’re supposed to do—ease is the real goal. 

Sure, there are people out there who eat dry grilled chicken with plain brown rice every day and work “boring” data entry jobs, but I’d venture a guess that the repetition and predictability of those choices is just what works for their personality types. 

The next time you’re tempted to look at someone else who seems to have it all and think, “Gosh, it just seems so easy for them,” you’re probably right! They probably are doing something that feels easy to them, and that’s why it’s going well. That’s how they manage to do it. 

They’re not harder working or smarter or better than you—they’ve just stumbled into alignment.

My new part-time job was at a gym’s daycare center, so I’d typically head there after school, do my four-hour shift until about 7pm, then venture upstairs (free gym membership, baby!) and walk on the treadmill for about 45 minutes. While I exercised, I’d review my notes for that day. I’d read through them as many times as I could over the course of the walk, and then head home and finish the rest of my homework.

In retrospect, this sounds like a pretty exhausting existence (or a testament to a 17-year-old’s boundless energy reserves). But this approach—spreading out the misery of my test prep with an hour of leisurely, low-pressure note review each day vs. panic-cramming for the 48 hours before each test—enabled me to start acing tests with very little “official” studying. My weekends before tests were (regrettably) spent running from the cops or (not-regrettably) hanging out with my parents instead of being holed up in Nina’s room practicing geometry.

The repetition of this daily routine paid dividends, literally and figuratively—while I did relatively well in school my freshman and sophomore year, my grades junior and senior year scored me an out-of-state college tuition scholarship that was worth, at the time, about $25,000 per year (and based on how the cost of college has risen since, I’ll assume it’s now worth $250,000 per year—#SadJokes). 

I didn’t have to sacrifice sleep, be a genius, or do anything exceptionally difficult: I just had to spread out the misery such that each day featured a little bit of work (no “off” weekdays), but no one day featured a lot of work.

Doing a little bit every day was more manageable than the alternative, and it generated better results—it didn’t require exceptional performance during high-pressure periods (i.e., in the days leading up to an exam), but instead took advantage of my regular ebbs and flows. I’m sure there were some afternoons when I retained more, and others when less material made it through my thick-ass teenage girl cranium, but I dollar-cost averaged my effort.

So often, I talk to young professionals earning above-median (in some cases, well above-median) incomes who feel as though there’s no point in investing in the stock market until they earn $X more (“X” is irrelevant for the sake of this example, but anecdotally, it’s usually about 20% more than whatever they’re currently earning). They’re delaying their misery until an unspecific point in the future that they assume will be less miserable, thanks to having more money on hand. But what does this often mean in practice? Forcing yourself to go above and beyond once you reach your forties and fifties. 

Part of the reason we have a tendency to do this, I think, is because we overestimate the struggle awaiting us—we assume we’ll need to turn the dial way up in order to make progress at all, and the idea of doing so seems unbearable (or flat out impossible) in our current state. 

But you don’t need to cram the misery into a single decade or two. You can spread it out. The thing is, spreading it out over time requires prioritizing it now—even if it’s just “a little every day.” 

Comparing these two strategies

Retirement is life’s ultimate financial pass/fail exam. 

Some people start paying more attention as they see retirement looming on the horizon—the metaphoric Tuesday before the Friday test—and spend the intermittent days (years) sick with an undercurrent of anxiety, aggressively cutting back on their spending at the exact moment when they’re probably most interested in letting loose, and realizing they may need to work for a lot longer than they realized. 

They’re forced to cram a lifetime of financial pain into a few short years. 

Compare this with the “spread it out” approach. Rather than struggling to dump 50% of your income into your 401(k) and IRA at the last minute and giving it very little time to compound before you’ll need it, diverting 10% earlier in life (a much smaller sacrifice!) means you’ll likely never need to save more than 10% at a time. This is true even in the years leading up to the big day, when you pull the ripcord and float away from Zoom calls and work alarms forever.   

The chart below illustrates the contribution patterns of the two “paths,” one wherein someone saves 10% for all 40 years of their working life, and the other where someone realizes in year 30 (about 10 years before retirement) that they need to kick it into gear. (This assumes two earners who both take home $50,000 per year after taxes in year 1, rising by 3% per year.)

The person making consistent 10% investment contributions never invests more than $15,800 per year over the 40 years. The “cramming” investor must start investing in year 30 with a $58,000 contribution.

The red investor gets to go balls to the wall with the AmEx for the first 30 years, but notice how similar their spending is for the majority of their working lives, despite how different their last decade looks:

It looks like a negligible difference in spending…until it doesn’t. The blue investor got to spend 90% of their income through all 40 years—whereas the red investor got to spend slightly more until year 30, but then had to drop down to a harsh 50% for the last 10 years. 

And of course, if you’re familiar with how exponential compounding works, you may already know that the 10% investor will skid into year 40 with more money. The chart below illustrates their respective account balances, using an average annualized rate of return of 7% in both cases:

The 10% investor will have almost $1.6 million in today’s purchasing power in year 40; the “cram” investor will have a little over $1.1 million. But with the red investor’s high save rate, they’d catch up to the 10% investor if they worked and saved 50% for an additional six years.

(In order for them to retire with the same amount as the 10% investor at the same time, they’d need to maintain a 70% save rate for the last decade.)

Is it easier to save 10% for 40 years or 70% for 10 years?

If you’re trying to retire early, a 10% savings rate probably won’t cut it (try 15% or 20% if that’s your goal). But if you’re happy to retire on time (which is no small feat!), a lifetime of investing $1 of every $10 you earn—spreading out your sacrifice—will do the job.

And while it depends on how your income changes (and maybe your personality, too), I’d wager that a consistent 10% savings rate is almost always going to be a walk on the treadmill compared to condensing all your sacrifice into one big sprint at the end.

Plus, I think you might be surprised to see how our revenue and expenses break down (hell, I was surprised). 

Moreover, my experience building a business within a business has been interesting since Money with Katie was “acqui-hired” in January 2022 by our parent company, Morning Brew. Prior to that acquisition, I was a solopreneur, and my revenue was roughly $250,000 in Year 2 (an infinite increase from Year 1, when I made $0). 

The acquisition meant that I would join the Brew to run the franchise and have access to part-time resources within a larger, more established media business, and…well, the results speak for themselves.

We don’t gatekeep in Money with Katie Land (if anything, we prefer gate-opening), so without further ado, here’s how the franchise made money last year, plus key takeaways () where applicable:

“Direct to Consumer” Revenue: $663,048

Affiliate revenue, merchandise sales, Wealth Planner sales, and educational products, like our Budget Like a Millionaire and Tax-Smart Investing master classes (though the second didn’t launch until 2023).

Affiliate revenue ($83,801): One of our revenue streams is affiliate links for credit cards that we recommend in our Travel Rewards content, but it’s really our only source of affiliate income. While affiliate revenue is a popular choice for many creators who organically plug products they believe in, it’s not part of Morning Brew’s broader sales strategy, which means it’s a smaller one for Money with Katie, too. 

I think of affiliate revenue like a double-edged sword—it can be truly passive, but I think it works best as a “quality over quantity” game. In our world, it was more beneficial to focus explicitly on a small handful (and now only one!) high-value affiliate relationship that was easy to build into content we would’ve been making anyway.

Merchandise sales ($107,318): Think our trademark RETIRED sweatshirt, Rich Girl Summer koozies, and the “Mom, I Am a Rich Man” line. We did a lot of testing and learning around product in 2022, and ultimately decided that while certain kitschy offerings are fun, we mostly want to focus our efforts on functional tools rather than branded merchandise.

Frankly, I was surprised this line of business did this well. Our best merchandise products played off something happening in real time within our community, like the My Qualifications mug, which spawned from a cold DM I received from someone who told me our feminine branding was “off-putting” and that we could reach more people if we’d drop it. The message closed with, “As a straight man, I can assure you my opinion carries weight.” I shared the DM on Instagram Stories and said I wanted to put it on a coffee mug—then we did, and it sold out overnight. On the flip side, merchandise that we developed in a vacuum sat on the shelves.

Wealth Planner sales ($407,750): This is our flagship, core product, and the apple of my eye. In the UX world, we did something called dogfooding (eating your own…dogfood? I don’t know, it’s a metaphor that leaves a lot to be desired), or using your own product in order to help make it better, and man, that’s been true for the Wealth Planner. I’ve been eating my own “dogfood” since Day 1, which means I think of new enhancements almost every month. We try to keep the price point accessible for this product, but also want to avoid making it so cheap that it inadvertently suggests it’s a low-value product. We just kicked off development for the 2024 Wealth Planner, which will launch in November, because it typically takes 5–6 months to get it right.

The Wealth Planner is by far our biggest single source of revenue, and it’s also the line of business that makes me proudest, because I know how impactful it can be in someone’s financial life. The pricing of a digital tool is always the tough part, and we’ve increased the price incrementally over the years, as we’ve had to invest more money in development and as we’ve made the functionalities more robust. Having a staple product that you know will work for most everyone in your community (because it directly addresses the reason they’re interested in your work) is nonnegotiable for a creator-led business (Thomas Frank addresses this in this week’s episode, too).

Educational products ($64,179): This is an area we’ve devoted more resources to in 2023, after assessing where we want to be investing more of our time and energy. It hadn’t historically been a major focus for us—probably because we give away the vast majority of the value we provide for free to our audience (made possible by an advertising model). Our courses focused on a deeper dive into budgeting and building a spending plan that actually works, as well as tax-smart investing philosophies that aggregate all the goodness of the tidbits you’d find strewn throughout our blog posts, podcasts, and social media into a coherent curriculum.

I struggle with courses, mostly because of the price point. It’s an area where I know we need to improve, because we get questions all the time about more advanced offerings. We tried a cohort-based course in early 2022 and ended up not moving forward with it because we didn’t have enough sign-ups to cover our expenses; this was a big surprise for me, as I figured live courses would be preferable to asynchronous learning. Turns out people don’t want to air their financial grievances to strangers—which, fair.

Advertising Revenue: $489,465

Ads sold for the newsletter, podcast, and social media (though our social media sponsorships are all part of our larger podcast sponsorship; we rarely do one-off social media campaigns that aren’t also part of a broader campaign).

It’s difficult to delineate advertising revenue by product because we don’t typically sell things à la carte (instead, a full package for a sponsor might entail coverage on all our properties), but we tend to work with fewer, large sponsors as opposed to a ton of smaller ones.

Total 2022 DTC + Advertising Revenue: ~$1.152m

Adjacent sources of revenue ($30,123)

On the side, I’ll sometimes do corporate speaking engagements or seminars for large groups, but this isn’t something I actively seek out, as running the business described above takes up most of my time. 

Expenses

Ah, yes—the non-fun part of the equation. How much does all of that cost? 

Merchandise ($31,280): When you sell physical product, you first must buy physical product. 

Delivery and production ($39,546): Software, tech products, and other production costs. 

Salaries, wages, healthcare, 401(k) matching, contractors, and payroll taxes ($502,113): The “people” costs side of the equation, and by far the largest line item.

We’ve also expanded in 2023, which means our staffing costs have increased—but in 2022, we were a one-woman show (read: me) until May, when we made our first full-time hire: Henah, my executive producer. (You know her! You love her! She’s…my Rich Girl Roundup costar and the wind beneath my wings.)

There are some other smaller costs—a few thousand dollars for travel, a couple hundred bucks in office supplies, some small licensing fees, etc.—that I’m not including here because they cumulatively don’t add up to more than $10,000 (1% of our budget, based on revenue).

And, of course, three big lessons learned

1️⃣ The importance of hiring well. Our first full-time hire, the aforementioned Henah, came directly from Rich Girl Nation—and her involvement in the business made a world of difference last year when I was drowning on my own. It’s hard to overstate how crucial proactive competence is in the early stages of a business (or how damaging it can be when you’re either understaffed or incorrectly staffed).

2️⃣ The challenges of a creator-forward business model. Sometimes your biggest strength as a creator brand (i.e., the ease of relying on your own personality and opinions) is also your biggest weakness. There are obvious issues with long-term scalability when the brand ethos is so dependent on one person, as well as the fact that—at any moment in time—everyone could decide they think my voice is annoying and my takes are bad and, well, that’s the end of that! We’re actively thinking through how to address the potential vulnerabilities this introduces.

3️⃣ Trying to do too much. It’s so easy to get distracted in an entrepreneurial landscape that’s constantly evolving, and I have to continuously remind myself that we need to focus on our core competencies and what actually matters for our bottom line and larger goals. Aka, not virality on TikTok or rapid “follower” growth on Instagram, but instead producing an incredibly high-quality show every single week and delivering enough value to our newsletter subscribers to make them feel as though the time they spend reading is well spent. I had to reevaluate where I was spending the bulk of my time at the end of 2022, and realized I was falling too often into the trap of petty metrics (How many plays did that Reel get?) and not enough time on the higher ROI activities, like researching and writing.

Looking forward

There’s a saying I like in business (and life, I suppose): “What got you here won’t get you there.” 

The pure relentlessness of my obsession and a truly serendipitous full-time hire helped us scale from $250,000 to $1m in annual revenue, but in order to reach more people with even better products (whether that be the podcast, the Wealth Planner, or something else entirely), we need to make sure we build systems that support us (vs. just brute-forcing our way through the week, every week). 

Part of this entails making sure each person in Money with Katie Land is operating in their zone of genius for the majority of their time spent working. And once we’re confident we can run our existing platform(s) excellently (and like a well-oiled machine!), we’ll be able to explore things like four-day work weeks, new lines of business, and more unique opportunities.

Every time I read something about negotiating a salary, a major takeaway is usually that everything is negotiable—e.g., if Corporate Daddy won’t budge on base pay, you can negotiate more time off. A few extra days off would be great—but usually, I want more money. I can’t invest my PTO in a Roth IRA (well, unless I quit and cash out, which is a viable short-term strategy).

Until I started my own business, I had always worked (a) for big companies with monstrous compliance departments that standardize everything and basically won’t budge on that type of stuff and (b) at levels low enough in the organization where negotiating the “extras” isn’t really on the table.

(If you’re negotiating as a director, vice president, or some other high-level position with a compensation package that screams “I have a price and you better pay it,” you may have better luck!)

Preparing for a negotiation and quantifying your track record

I agree with the advice that you should track your wins at work and measure them where possible, so you can unfurl your scroll of badassery when it’s time to talk about promotions.

If you’re saving the company money or earning the company more, the negotiation should probably go in your favor. The most common issue with this advice, I’ve found, is that the company likely already expects you to earn more for them or save them money in some capacity. Numbers that illustrate you’ve somehow gone above and beyond the scope of what your role is already compensated for are the real needle-movers.

This is probably stuff you’ve heard before, and when it works, it works! 

Negotiation tactics matter, but they’re not the most important thing when negotiating on the “inside” of your current company

The most important thing—from what I’ve observed—is having an engaged network of advocates inside. We’re talking about other, more senior employees (ideally including your manager) at the company who (a) know you and (b) are willing to go to bat for you. Without this, it’s going to be very difficult to negotiate.

This is less about the words you say in the negotiation itself, and more about laying the groundwork over time. How you do your job when you’re not negotiating typically impacts the negotiation most.

The cool thing I noticed during my time in Corporate America is that you didn’t have to go the extra mile to stand out—usually, going the extra yard was enough. A few examples: 

• If your deadline for a project is Friday, hand it over on Thursday.

• If you have a standing 1:1 with someone whose opinion impacts your compensation, send an agenda ahead of time and manage up. 

• If you’re asked to pull a report on three factors influencing conversion, throw in a fourth. 

• If you’re bringing an issue to someone, come prepared with one potential solution, too. 

It doesn’t mean you need to be on Slack on Saturday mornings firing off compliments to everyone on payroll—but the “extra yard” mindset goes a long way in building a disproportionately robust perception of your work ethic that doesn’t typically take that much additional work or time.

You can be the best negotiator in the world, but if you’re not good at your job, it doesn’t matter. So much of the negotiation happens before you even come to the table.

That said, if you’re working this way and not moving “up” (whether via raises or promotions) at least once every ~24 months, it’s probably time to strongly consider looking elsewhere. Sometimes leaving is the best thing you can do for yourself.

Now that we’ve covered our basics, let’s talk about the overarching truth I’ve noticed in the last few years of negotiations. 

The person who cares less wins.

If you enter into a negotiation willing to walk away, you suddenly have basically all the leverage.

Now, that’s easier said than done, as most people kinda care about maintaining their employment—but operating from a position of “I don’t need this” shifts the perception of power to your side. 

That doesn’t necessarily mean that you’d actually walk away if you didn’t get exactly what you wanted, but entering into every negotiation with a floor (the lowest offer you’re willing to concede) helps you stay strong in the face of pushback.

It also doesn’t mean you’d approach the negotiation with a flippant or careless attitude. It just means that the person who’s operating with optionality on their side automatically has more power.

So how do you put yourself in that position authentically? It’s actually pretty simple: Have a better offer. 

This line of strategy works best if you’re negotiating with a company you’re already employed by, because it gives you the time to get your ducks in a row before coming to the table.

Negotiating with your current employer

Whether that better offer comes from another company, your own business, or a different team inside your current company, you immediately uplevel your negotiating position when you can share—in the spirit of transparency, of course—that you’re weighing your current role against another opportunity. 

While there are plenty of Jedi mind tricks and pricing approaches you can learn from negotiation experts (and we’ll explore some of my favorites in this week’s YouTube video), this is the ultimate cheat code. 

It cuts out all the verbal gymnastics and careful scripting and “win” documentation and boils it down to a very simple, very primal truth: You can walk away if you don’t get what you want. 

That essentially forces the other person to offer you the most they possibly can for what you’re worth to them, and if it’s not enough to be worth your while, you have a decision to make. Stay where you are, or walk.

There’s another upside to employing this strategy: It helps you explore the job market and understand your market rate. 

How do you efficiently secure another job offer?

I’ll state the obvious first: Yes, any other better offer will do, but you’ll get the most juice for your squeeze here if it’s a job offer you’re actually excited about. Apply to companies in your field that you’d be excited to work for. 

How to go about the application process, you ask? 

Well, in my (limited) experience, there are a few best practices that helped me land great gigs:

Leverage LinkedIn. You don’t have to start posting LinkedIn humblebrag monologues or cosplaying a VC, but making sure your LinkedIn profile is #optimized will work wonders. Describe your “position” on your profile in such a way that it’ll be a search result for the types of jobs you want (i.e., if you need to massage the verbiage of your current role a little, do it—they don’t always translate company to company, and you want LinkedIn SEO on your side when recruiters are hunting for new people). 

Personal anecdote: I was a Brand Copywriter at Southwest Airlines when I started working there and eventually ended up doing mostly UX Writing and training under our Principal UX Designer. My official title at the company? “Associate Manager of Customer Strategy.” Bitch, what is that? Nobody knows. I wanted to continue pursuing the path of becoming a UX Writer, so I called myself a UX Writer on LinkedIn, because that was effectively the work I was doing anyway. 

I had the portfolio pieces and experience to back it up, but I would’ve looked qualified for the absolute wrong types of jobs had I called myself what my company was calling me. Calling myself a UX Writer got me hired at Dell (which added another feather in my resume cap), and I began getting recruiter messages from Google, Facebook, JPMorgan Chase, and PayPal for UX Writing jobs—all because my LinkedIn profile was crafted to be a magnet for those types of positions.

Cast a wide net and embrace rejection. Back in the summer of 2020, I was applying for jobs like I was unemployed. I used the “Jobs” feature on LinkedIn to find and apply for roles. It became my little employment hub.

Any company that excited me got an application. Spotify? Check. Pinterest? Yep. Google? Double-yep. I went application crazy and got (mostly) flat-out rejections. I ended up in lengthy interview processes at NerdWallet and PayPal, and eventually ended up getting an offer for a contractor role from Dell. 

The point is: You’re going to get told “no” a lot, but it doesn’t matter. You only need one “yes” to have another offer in hand that you can leverage. If it’s less than you make now, maybe your current market rate is actually lower than you think for your level of experience—or maybe your current employer is actually pretty good, and that’s worthwhile information to know, too.

Molding your experience for jobs you actually want

If you’re casting a super wide net, you can’t mold your profile to fit every single application—but it’s worthwhile to open 5–10 job postings that appeal to you on separate tabs. Look for common phrasing or experience requirements, and make sure you’re using the same type of language that’s coming up frequently in your own profile.

Practically every single job I’ve ever gotten (or had a good shot at getting) had nothing to do with who I knew or what I applied for—it happened because something on my profile showed up in a recruiter’s search. 

But if you’re reading about negotiation, you’ve probably already got your job offer

Great, so we’ve hit the high points on how to get another offer that you can leverage in a negotiation with your current employer. What if you’re negotiating with a new company? 

Negotiating with a new company that’s offering you a job

Know that it’s unlikely the number they’re coming in with is the top of the range they’re authorized to offer. (It’s probably nowhere near the top, unless you’re way overqualified.)

All that to say: They’re giving themselves breathing room because they’re expecting you to negotiate. When you’re in that position, there are a few things you can discuss regarding your old compensation that can help juice it a little and give you some leverage:

• Your old 401(k) or HSA match, if you had one

• Your old bonuses or profit-sharing

• Any other benefits that had monetary value

Stack that shit one on top of the other: If your base pay at your old employer was $60,000 but they gave you a $4,000 match, a $1,000 bonus, and a $500 stipend, your old compensation wasn’t $60,000. It was $65,500.

If your new offer from another company comes out the gate at $72,000, you can say:

“Thank you so much for the offer. I’m so excited about this opportunity and really grateful for it. My current compensation is in the high $60s, and in order to make leaving my current role worthwhile, I’m hoping for at least a 15% increase from my current compensation. Is $75,000 doable?” 

If you have other bargaining chips, like being overqualified or leaving your current company before a bonus hits, you could ask for even more. 

But in that one (totally reasonable) request, you may have just increased your base pay from $60,000 to $75,000. It’s only $3,000 more for them (a blip!) but a meaningful increase for you.

Just make sure you’re actually happy with the number you’re proposing. If they say yes to it, it’s likely the negotiation ends there. You can’t exactly come back later and say, “Cool, so what about $78,000?” 

The reality, though, is that you’ll probably already get offered quite a bit more than what your current employer is paying you, so this trick only works if you can juice your current compensation enough to give yourself that springboard.

I’ve used this tactic three times and it’s never failed me.

If for some reason it doesn’t work, you can try leveraging a bonus (or other reward) from your current position that you’re forgoing in the job switch for a one-time signing bonus.

For example, if your current employer does a cash bonus or profit-sharing of $5,000 per year and you’ve been offered a new job a few months before that’s scheduled to hit, you can use that “lost” bonus as a bargaining chip:

“I’m so excited about this opportunity, but I’m set to receive a performance bonus at work in a couple of months, and since I’ve earned it, I’d really like to receive it on principle. Would you be open to matching it in a signing bonus?”

(These scripts aren’t gospel, but hopefully they illustrate the point.)

What about research using Glassdoor or other sites that share salary data?

This information can be a little difficult to wield tactfully, depending on the relationship you have with the manager or recruiter in question.

“Well, Glassdoor says the average salary for this job is $82,000, not $75,000.”

You may be met with a, “Cool—and?” unless you have a masterful way of leveraging it. I like to use these ranges on salary transparency sites as guideposts for what I can talk a recruiter up to for an unrelated reason (or, if you have a good relationship with your manager, a less clandestine approach may work just fine).

For example, you make $60,000 ($65,500 when padded; let’s round up to $66,000), they offer $72,000, but you see $85,000 on Glassdoor. 

(There’s a chance it’s higher on Glassdoor because those inputting the self-reported data have more experience, but that’s neither here nor there—you still want to ask for what you think you can feasibly get.)

If you have $85,000 in your head as the “average” or the “ceiling,” you really just have to come up with a reason to inch closer to that. You’ve heard my go-to tactic, but unless you’re obviously overqualified or have an extenuating circumstance you can wield, it may be difficult to play the “I’m worth more” card until you’re actually inside and can ~justify~ said value.

You’re probably aware (if you’ve gone through the job application process before) that the recruiter will ask for a ballpark number. This is to make sure your expectations for the role’s compensation are on the same planet as what they can actually offer you, so they don’t waste your time (and vice versa). I know traditional advice is not to give an answer, but I think there are creative ways to approach this in states without salary transparency laws.

How to answer the question, “What are your salary expectations?”

While this question can feel like a trapdoor, how you answer it depends on where you are in the process.

Let’s say you’re only willing to leave your current company for $70,000 or more, but you’d be thrilled with $80,000. If the top end of their range is $60,000, you’d probably rather know that up front so you don’t waste your time in the interview process (and if there are other openings that are better suited for you in the company, they can shuffle you there instead).

Refusing to give a number or deflecting can make it seem as though you’re not sure what you’re worth or what the role should pay, so if it’s early in the process, I like to say something like this:

“It’s hard to specify a target right now without knowing what the role entails and what success looks like, but I’m hoping to be somewhere in the (here’s where you give a very padded range!) $75,000 to $85,000 range.”

It’s unlikely you’ll undershoot a realistic estimate if you Glassdoor-stalk the role ahead of time, though there’s always a chance they had you pegged at $95,000 and now they’re looking at you with dollar signs in their eyes because they know you’ll probably take $80,000. It’s a risk you can mitigate with proper due diligence. 

If you’re just a little over what they can offer, they’ll tell you, but I went through a screening call once where I told them I was expecting something in the range of $120,000 to $140,000 and they told me flat-out that the cap for the position was $95,000, but that they’d keep me in mind for more senior roles in the future. 

If I had played coy, I would’ve been majorly pissed after wasting all the time on the process to learn the maximum salary was way below my target.

I know this isn’t traditional advice, but in my experience, throwing out numbers that actually excited me has never backfired. 

I’m not an expert

…but I think my track record speaks for itself:

• 2017: Started at $52,000 (didn’t negotiate because this was more money than my 21-year-old self could fathom)

• 2018: Negotiated a raise after one year to $60,000 (15%)

• 2019: Negotiated another raise after another year to $66,000 (10%)

• 2020: Switched companies when I was offered a base pay of $108,000 (when I made the copywriter > UX writer switch!) (63%)

• 2021: Negotiated up to $115,000 (6%) with $25,000 in bonuses and stock for a total compensation of $140,000

…and now I’m a post-acquisition business owner who’s faced with tough negotiations more than I’d like, and still trying to find novel, better ways to increase my income.

A wealth gap so gappy, it makes the Boomers look egalitarian

The young adults of today are shuffled into a system that creates even bigger winners and losers than the one their parents’ generation faced—which means they may find themselves priced out of the lifestyles they enjoyed as kids, even if their professional success rivals or even exceeds that of their parents.

According to data from the Federal Reserve’s 2019 Survey of Consumer Finances, the median net worth of someone aged 30–34 is about $19,000—while the net worth of a “Top 1%” 30- to 34-year-old is $1.37m. That’s a whopping 70x larger than the median for the age bracket. 

The story is even more damning for the 35–39 camp, where the median net worth is about $36,000 while the 1% net worth is $2.8m—77x larger. 

For comparison, the “60–64” group that’s inclusive of boomers has a 1% net worth that’s 60x larger than their median counterpart, and the 65+ camp’s 1% net worth is 54x larger than the median. A veritable socialist utopia, huh?!

So that’s median and 1% — but what type of wealth is considered “middle class”?

According to Pew Research Center, the median wealth (adjusted for inflation) of someone considered “middle class” overall in the US is $125,000. If one examines the “middle-of-the-road”-aged millennials (those 30-34 in 2019 when the data was collected), only the top 20% had a net worth that hit this middle class median wealth threshold. Those in the 20th percentile had a negative net worth, and those in the 50th percentile had a net worth of around $20,000.

You could probably explain some of this away by the simple factor of age; it’s common to have more debt when you’re young and accrue more wealth over time as your investments compound (for example, the median net worth for the “50-54” crowd was $122,000). 

For that reason, it’s probably fair to say that young people have a decent shot of aging into middle class wealth.

But how do we explain the sub-cohort of millennials that are thriving far beyond the historical average, when the majority clearly aren’t? 

Meet the millennial 1%

So how much do you need to earn to call yourself a millennial 1%er? 

Based on income alone, if you’re under 35, you’re a “top 1%” earner if your household earns more than $225,000. Something to #strive for, I suppose. 

My friend Nick wrote a great piece on Of Dollars & Data, so please enjoy this chart he labored over that shows top percentile earnings by age range:

And while income can be a good indicator of financial success, net worth tends to be a heartier measure of “things going right for longer,” as it’s more permanent than income (that can go away with little warning). To have a 1% millennial net worth (aka to be in the top 620K of the 62M existing millennials), you’d need to have socked away between $600,000 and $2.8M, depending on which cohort you belong to within the millennial spectrum. 

Sure, a 25-year-old can luck into a really great gig earning $250,000 per year—but how does one amass $2M by age 30? 

That’s a little trickier, and requires more digging. 

Because most millennials are still too young to have amassed decades of wealth from a successful career, the biggest factors in millennial net worth outcomes are whether or not they have student loans, if they own property, and their incomes. (Note that two of the three are strongly correlated to the amount of wealth their parents have.)

Because who are the millennials’ parents? The Boomers, baby! The Boomers, who are collectively poised to pass down approximately $70 trillion, are the single-richest group on planet Earth. 

(They hold more than half of all US wealth, and control about 17% of all wealth globally, a fact that really begs the question: How do we recreate the post-WWII economy without another World War?)

Student loans & property

I asked Canadian personal finance expert Bridget Casey, who wrote a piece called “There Is No Such Thing as a Millennial Middle Class,” to weigh in on the show this week, edited here for brevity: 

“It’s called the ‘Funnel of Financial Privilege.’ If someone receives some financial advantage from their parents, there’s a high likelihood that they received others—and those benefits tend to accrue. 

Someone whose parents could afford to give them a down payment are likely the same parents who could afford to pay for their post-secondary, who tend to be the same parents that can probably afford to pay for a good chunk of your wedding.

It becomes a funnel that pushes [their children] to a really high net worth much earlier in life than people who didn’t have any of those advantages.”

So it stands to reason that millennials whose parents foot the bill for college (and maybe even gifted them the down payment for their first home, or provided an interest-free loan) are in a radically different position today than those who did not have this leg up. 

Now, I realize that “some people just have rich parents!” doesn’t feel like a particularly revolutionary finding, but there’s a double whammy at play here: Not only did access to family capital allow this group to avoid taking out debt early in life (debt that doesn’t have an appreciating hard asset to offset it, mind you), but it also granted them access to an asset class that was on the brink of being propped up by expansionary monetary policy. 

Real estate’s all about timing, and millennials were between the ages of 15 and 30 in 2011 when the real estate market bottomed. The eldest millennials were in a prime position to buy their first properties right as real estate was cheapest. And it wouldn’t remain cheap for long, though as long as you got in before 2020, you saw the value of your asset skyrocket. 

Elder millennials with generous parents (or highly paid jobs!) were well-positioned to take advantage of one of the largest downturns in history. 

This theory sounds intuitively true, but is it accurate? We can pressure-test it: According to a Coldwell Banker luxury report that’s cited ad nauseam online, 92% of millennial millionaires own property. The average number of properties a millennial millionaire owns is 3, and their average real estate portfolio value is $1.4M. 

And because real estate is an asset class that primarily uses leverage to generate returns, this group’s parents wouldn’t have to be the yacht-owning, company-leading, Rockefeller types—a single, large cash infusion from a decently well-to-do family member at the right time can spark a mushrooming real estate portfolio, if you know what you’re doing. 

Of course, that’s not to suggest that every millennial real estate mini mogul got a large cash infusion from a family member—unfortunately, there’s no data to tell us how common that is. But it stands to reason that those with generous parents were more well-positioned than those in generations past, if for no other reason than the housing crash in the early aughts was the largest of all time.

Will the “Great Wealth Transfer” be the Great Equalizer? Probably not

According to Cerulli Associates in 2019, millennials are estimated to inherit $68T from the Boomers over the next decade or so. On its face, this sounds (?) like a good thing—the millennial generation as a whole is about to get a hell of a lot richer and close the gap, right? Start buying shares of $SBUX now!

Wrong! The Federal Reserve’s analysis shows that millennials who are already in the top 10% of the income distribution are twice as likely as millennials in the bottom 50% to receive an inheritance.

Per New York Magazine, “The millennial rich and upper-middle class will be the wealthiest [generation] America has ever known. Working-class millennials, meanwhile, are poised to enjoy less economic security than their parents, as their wages fail to keep pace with the rising costs of housing and health care.”

Based on these two factors alone—higher education costs and housing—you start to get two radically different classes of millennial experience, and variations of the two somewhere in between.

So what’s a 99% millennial to do?

History would tell us that—to some extent—it’s statistically likely that more of this generation will age into the middle class over time. 

But tactically speaking, if you’re dealing with student loans, can’t afford a house, and don’t stand to inherit a bunch of money from your rich-ass Boomer parents, there’s really only one piece of the puzzle we touched on today that doesn’t rely as fully on external factors: Your income. 

Developing more marketable skills, working to surface more opportunities more frequently, trying different things…these are the highest points of leverage for many young people without the other tailwinds we described today, like family wealth or a house you bought in Boulder in 2012. It’s where your time and energy are likely going to go the farthest and provide the highest ROI.  

If you’re trying to determine where to focus your energy as a millennial in 2025, I think the answer is clear, if dystopian: Human capital.

Practically overnight, I went from working my full-time job in content design and building Money with Katie on nights and weekends to being a full-time content creator with a generous contractual security blanket, binding me to a benevolent media company safety net (and health insurance plan) for 36 months. 

This classic “success story” is almost so cookie-cutter that I have to double-check sometimes that it’s actually happening to me, and that it’s not some cubicle daydream. My November 2022 life would have been almost unrecognizable to me from my November 2019 vantage point.

But the popped champagne, spilled tears, and breathless, “Holy shit, I can’t believe this is happening”s that filled our kitchen when I signed the contract were not solely the culmination of a month’s worth of Zoom negotiations and lawyer-approved emails.

In fact, it probably never would have happened had I not gotten a traffic citation three years earlier.

Wait, what? A traffic citation?

Sometimes, we mischaracterize luck

That’s because my internet friendship with Morning Brew’s CEO didn’t begin in November 2021—it began in the spring of 2018, when I was pulled over for reading Morning Brew at a red light. 

A few expletives later (and after safely parking my vehicle at work), I tweeted to let @morningbrew know just how much I loved their product—enough to pay a $150 citation to read it from my phone at a red light.

Austin noticed, followed me back, and DM’d me: 

“Hey,” he said, “That’s hilarious. We’re going to pay for the ticket.” 

And thus began an internet rapport—a loose, random connection that almost wasn’t, but a connection that meant when I launched Money with Katie two years later, it appeared on a feed of content mainlined to Austin’s phone. 

Had I not been pulled over that day, I’m not sure we would’ve ever crossed paths.

Had I not tweeted about it, I doubt he would’ve ever seen Money with Katie on his feed.

Had he not been the guy manning the Brew’s Twitter account back then, I’d probably be sitting here at 1pm on a Thursday working on an app disclosure screen for Meta (if I weren’t laid off!), not on this blog post.

It was dumb fucking luck. 

We make thousands of decisions every single day—the problem is, we don’t know which ones are consequential

We pick the early flight instead of the late one. We go for a run down this street and not that one. We try the new coffee place on the corner, or we go for kombucha instead.

If you sit back and consider the sheer number of choices you’re faced with on a daily basis, it’s enough to make you curse The Butterfly Effect and hide in your room. It’s dizzying, because we never know which choice is going to catapult our lives in a completely different direction.

A traffic citation is innocent (albeit stupid) enough; at the time, I beat myself up over it for the remainder of the week, taking it as proof that I’m bad at following rules and if I weren’t always running so late all the time maybe I wouldn’t have felt like I needed to check email in the car, plus a number of other “adult” things I considered myself “bad at” at the time.

In retrospect now, though, it’s clear just how fateful—how significant—that seemingly insignificant stupid decision was. 

And sure—maybe Austin and I would’ve crossed paths some other way. Maybe I’ll look back on my decision to pursue Money with Katie full-time someday and consider it the humble beginnings of totally different, exciting things. Maybe the path I’d be on right now had I not been pulled over that day (and tweeted about it) would be infinitely cooler, better, and more enriching (though, seems hard to beat).

But I have no way of knowing, because I did get pulled over. I did tweet about it. And I did decide to take him up on it—and as a result of that sequence of events, I’ve reached a state of career fulfillment at age 27 that I could’ve only dreamed of just a few years ago while fighting tooth and nail for a 15% raise on a $52,000 salary.

Yes, I built Money with Katie in obscurity for 18 months before anyone looked twice at it (and to suggest I’m not still toiling away in relative obscurity is a stretch), and sure, that took some work. 

And many of us are pretty willing to admit where privilege has positively impacted our outcomes, but we often ignore the massive role of another factor that blindly bestows good or bad things upon us: luck.

To acknowledge luck’s role in our lives is to acknowledge we aren’t always the ones in control

One of the best pieces I’ve read about luck was a beautiful, thought-provoking exploration of a very tragic day: “It’s hard to come away from the stories of 9/11 with a sense of anything other than an appreciation for the role randomness plays in our daily existence,” writes Garrett Graff for The Atlantic. 

But there are plenty of positive examples, too: Bill Gates went to one of the only high schools in America with computer programming terminals. Gates himself estimates there were probably only 50 other students on Earth who had access to the same technology he did, and it was just the dumb luck of where he was born and attended school.  

Sir Alexander Fleming discovered penicillin when he accidentally left a Petri dish open during a holiday break and a specific type of mold fell into it and killed the bacteria, and 200 million lives have been saved as a result.

This is—for obvious reasons—incredibly disconcerting. We want to believe we’re the ones in control, that we’re the ones calling the shots. That our hard work (combined with, for some of us, privilege) will be enough to shepherd us toward the fate we deserve.

That if we work hard enough, and long enough, and sacrifice enough, we’ll be guaranteed the financial outcomes we are rightfully owed. The careers of our idols. The portfolios of our dreams.

To believe anything else would probably prove too demoralizing. 

Even the year you’re born determines how rich you become

Any time we talk about the bouquet of shortest ends of the stick that millennials collectively hold, there’s a glint of a silver lining that typically follows. Somewhere, deep down, I think we all believe we’ll still end up just as wealthy as the Boomers a few decades ahead of us. We hope that some intervening force—be it luck, privilege, or hard work—will correct the decades of bad breaks.

But even the stock market is not equally magnanimous to every generation of investors. It does not bequeath the same average annualized market returns on every retiree who skates into Naples, Florida on a Roth IRA and a dream.

As Nick Maggiulli points out, the year you’re born can be a pretty substantial determinant of how much wealth you accrue over your lifetime, all else being equal: Luck matters more than you think. 

Check this out:

Two people holding the exact same index fund for the exact same amount of time will have wildly different outcomes, depending on when they start.

Things smooth a little when you zoom out by 40 years, but there are still generations of investors who were far luckier than others:

Luck keeps us humble and hopeful

I can trace one of my most significant life events to a traffic stop four years ago, and you know what? That keeps my ass in line. 

The randomness of my lucky break hinged on an almost non-event—nobody knows how things would’ve played out if I didn’t break the law that day. 

Acknowledging the key role of randomness—from the year you’re born to the age you are when you stumble across your first piece of financial advice, to which obscure tweet makes it in front of the right person at the right time—reminds us that we are not the only ones responsible for the good things that happen to us.

Conversely, our decisions aren’t always to blame when things go wrong. That can help us remain hopeful for the future, and avoid the self-loathing that so often accompanies the belief that our lives are the perfect, equalized manifestations of our choices and nothing more.

As Mariel Beasley of the Common Cents Lab said in this interview for The Money with Katie Show, “We like to think that it’s our good decisions that are to thank for our positive financial outcomes, but a lot of the time, we’re just exposed to the right environments.” 

And what’s true about the environments we often find ourselves in? They’re also the result of dumb luck: The college that happened to be recruiting from your high school, the workplace that was hiring for your skill set the year you graduated, the family responsible for birthing you into this world…the year you were born!

Hard work works, but luck works, too.

To quote Seneca: “Luck equals preparation plus opportunity.” If you work hard to lay the groundwork, you’ll be ready when opportunity knocks—you just can’t control when it’ll go trick-or-treating in your neighborhood.

And ever since then, I’ve lived with this undercurrent of fear that—at any moment—something in the economy could shift dramatically and leave me without a paycheck. While this is likely a fear that everyone with gainful employment experiences, I’d postulate it’s more intense in the US, where your healthcare, retirement savings, and ability to pay for childcare are all tied to your employer. It’s a high-stakes arrangement, right? That’s enough to induce fear in anyone, regardless of how good you are at your job. 

So whether you’ve recently lost your job (or fear that you may for some reason), I wanted to put together a bit of a thought exercise: How to rationally approach a serious, scary situation to lessen the financial and emotional toll I imagine it takes. 

First things first—let’s usher the elephant out of the room

Yes, you are likely aware that you should already be searching for gainful employment elsewhere. We’re not really going to focus on the new job search—just the financial checkboxes you can start ticking off if you’re stressed about job loss in any capacity. 

And on that note, I apologize if any of this feels obvious to some of you, but I figured it made sense to round all of our bases and leave no stone unturned. Analogies abound.

For the purposes of this post, we’re going to assume there’s no juicy severance package or short- or long-term disability pay associated with the job loss—we’re assuming that for whatever reason, you’ve found yourself without the income you can typically rely on. 

That means the first thing you should do is look into applying for unemployment benefits in your state. This was a life raft during the pandemic when unemployment benefits were increased, but if you’re looking around at your savings coffers while doing these exercises and you’re only seeing cobwebs, it makes sense to apply for unemployment. Of course, there’s no guarantee you’ll get it, but it’s there for a reason—and you can get it even if you were let go with a severance package. Your tax dollars fund it. Use it!

Step 1: Analyze your environment. 

That’s a fancy way of saying: Figure out what you’ve got. Do a little inventory of your balance sheet and nail down a few numbers, primarily: How much do you have in cash readily available to you? 

This is probably going to be in checking and savings accounts, but it also might be cash that’s earmarked for things like emergencies, weddings, home improvement projects…and it can feel sketchy to start dipping into funds that were supposed to be for something else. I would note that you have it on your imaginary inventory list, but add caveats wherever savings were already dedicated to something else, and think of those as “last resort” options if absolutely necessary.

The other part of this analysis is figuring out what else you’ve got coming in. If you’re part of a partnership with combined (or pseudo-combined) finances, losing one job may not mean it’s all-hands-on-deck panic time. Same goes for if you’ve got side hustle income that can help eat up some of your impending expenses. 

On that note, a goal to strive for if you’re in a couple: The best way to insulate yourselves from job loss and compensation downturns is to live on one post-tax salary, and ideally, the lower salary. Why? Because even the higher-paying job is lost, there wouldn’t be a disruption in spending. That’s not always easy, though; for transparency, my husband and I are only about two-thirds of the way there in our own home. 

To summarize, in anticipation of (or immediately after) job loss, we’re taking stock of (a) what we have in cash already, and where, and (b) if there’s any other income coming in, and how much. 

Step 2: Calculate your runway.

This is where all the badgering I’ve done over the years to try to get you to figure out “how much your life costs” comes into play. We need to figure out how much heavy lifting our cash on hand needs to do (after all, if you’ve got side hustle income or another earner in your home who can cover some or all of the costs, you may not need to use much of your savings at all). 

We want to calculate how many months we have based on our current spending patterns. This mostly includes things that cannot be easily “behavior-changed” away—your rent or mortgage, utility bills, basic groceries, doctor’s appointments…stuff that’s more or less necessary even if you’re playing life on “Austerity Mode.” 

For those of us with the privilege of discretionary income, I’d venture a guess that not all of your spending every month is necessary, which brings me to step 3…

Step 3: Identify the costs we can cut.

When I think through our joint budget of $7,500 per month, there are a few major areas I recognize right away as opportunities to trim with reckless abandon:

• Cleaning ($200/month)

• Travel and the associated pet care (roughly $300/month)

• Meal prep service ($1,000/month)

• Restaurants ($400/month)

• Shopping and miscellaneous (call it $200/month or so)

Right there, that’s about $2,000 each month that I can just eliminate, shaving our budget down by about 25% to $5,500/month. 

Now, would I be happy to forgo these luxuries? Well, no—but I know I could if I needed to throw that ass in gear. The other big things (like rent, electricity, groceries, etc.) have to stay put, but my weekly takeout habit can go. 

This exercise should help you understand how far your existing cash cushion and/or other streams of income can be stretched once you “trim the fat,” but it brings me to my next major point…your liabilities.

Step 4: Think of any liabilities.

Look, I’m not saying you have to do anything drastic because you’ve lost a job. But if for some reason you feel concerned that it might be awhile before you get another one, or your existing cash cushion is relatively slim and you don’t have too many discretionary expenses to cut (because let’s be honest, having a ton of discretionary expenses in the first place is a pretty privileged starting position), it might make sense to look to your liabilities.

Do you have any remaining student loans in forbearance that you’ve been paying down anyway, that you could pause payments on? Could you consolidate credit card debt or do a balance transfer to get a lower interest rate and buy yourself more time? Do you have two cars in your household, and the ability to drop down to one? (With the thought being, you may be paying off two sets of car payments and car insurance and really only need one.)

The idea is, where can you offload liabilities? Maybe you’ve got a mortgage that’s a little steep, but you can rent out an extra room to a friend as a roommate and recoup some of that payment in rent. While Step 1 was about assessing cash on hand, this step is about looking around and figuring out…where are my current assets or liabilities either holding me back or providing an opportunity? 

Step 5: Figure out health insurance.

This one honestly irritates me, but alas, here we are (and by “here,” I mean: not in one of our peer nations where healthcare is considered a human right—but I digress). 

Was the job in question providing you or your family health insurance? This is something we don’t often think about until it’s too late, but determining your risk tolerance around going without insurance for a little bit is probably wise. 

Ideally, your spouse or partner is still employed and you can get on their coverage (or maybe you already were on their coverage!), but if that’s not an option, you may want to get a cheap marketplace plan in the meantime for catastrophic purposes like, if you required a procedure or service that would be financially ruinous otherwise. (In some states, there’s a penalty for not having health insurance.) 

So like…maybe try to lie low and table the extreme sports until you’re back on that late-capitalist, for-profit, employer-provided private healthcare. (sighs loudly)

Step 6: Check in with your mental state.

You never know how you’ll react to being laid off. Do an emotional assessment and see if there’s anything you can do to take action that’ll make you feel better. I know that—for me—I’d probably want to retain a sense of control. 

I’d probably be consolidating all of my cash in one place so I could keep track of it easily. I’d probably sell items that I didn’t need. If I still had a high balance on a credit card from when I was employed, I would look at doing a balance transfer to a credit card with 12 or 18 months of 0% introductory APR, so I knew I could buy myself some time and not have to pay it down immediately to avoid interest charges. (Note there’s usually a ~3% fee for doing so, but depending on the balance, it could be well worth it to buy the time and avoid the immediate interest and urgency-fueled stress.) 

The other thing to assess at this step is…do I want to rush back into the job market if I don’t have to? If you step back and assess your cash position and outgoing expense needs, you might find that you have quite a bit of runway and may have the freedom to think about this like a mini sabbatical. Even if the job loss was unexpected, if you’re in a financially secure position, it may be a blessing in disguise. 

I remember one conversation with an architect who found herself without work and decided she didn’t want to return to “white collar” America. Instead, she got a job in a local coffee shop that paid most of what she needed to pay her bills, and used her savings to supplement the rest for a little while, thereby extending her “savings runway” by quite a bit—she described wanting a change of pace and to do a job outside of the “knowledge work” sector. This could be a time to reinvest in yourself, depending on what your financial audit unveils—go back to school, get certified in another field that interests you, etc.

In conclusion…

If you’re feeling scared because the “worst case scenario” has already happened, or you’re just trying to prepare for the worst because you’re getting funky vibes from your boss Carol and you don’t want to risk it, know that your feelings are valid, natural, and—honestly—helpful, if they’re the reason you’re reading this blog post right now. 

At the very least, enacting these steps (whether before or after you’re faced with termination) will give you the two things that help most during times like this: security and control. (And hey, if you can coopt the unfortunate circumstance into the whole “sabbatical” thing…send pictures from Copenhagen, please. Word on the street is they’ll give you free healthcare.)

When we see major firms like this, it’s easy to forget that they were once…not major. Today, Vanguard’s market share is larger than their next-three-largest competitors combined, but it took them 20 years to reach 10% market share. 20 years! 

20 years of toiling. 20 years of Jack Bogle going toe-to-toe with Wall Street clowns and being told his idea was stupid and that his business model would never work and fighting for every single dollar under management. 

Bogle’s story is interesting in the way that Steve Jobs’s story is interesting—Bogle was booted from his own company and (creatively) came back with a vengeance to change the investing world forever. These are the small plot points in the retellings of their stories: They last for a single sentence, and then are quickly replaced with details of ingenious strategy. 

We forget that the single throwaway sentence of “getting booted from their own company” was not over in a few seconds (as our reading of its retelling is). They didn’t know what was going to happen on the other side of it, and it’s often not a quick, obvious move. (It took Jobs 13 years to make his way back! 13 years ago, I was 14. That seems like an eternity.) It’s easy to keep going when you know you’re going to win—but when you’re not sure if what you’re doing is going to work, investing thousands of hours over many years is decidedly less easy.

What’s impressive to me about Bogle’s story, though, is not that he built the second-largest investment firm in the world and didn’t even seize the opportunity to become disgustingly rich himself (a move that some deem “anti-capitalist”), but that he stuck with it for a grueling decade of net cash outflows every year (meaning…more money was exiting stage right than entering stage left). 

When we study these larger-than-life figures, we tend to remember the high points: Dude reads an academic paper about the validity of a fund that tracks an index (instead of actively picking stocks, as was par for the course back then), dude decides to invent said-product and bring it to market, dude becomes legend. End of story. 

Or is it? 

We often don’t pay much attention to the weeks, months, and years of toiling away and being told “no.” I’m not even talking about the daily work of building Vanguard: I’m talking about all the other false starts Bogle undoubtedly had. The weeks he probably wanted to peace out and do something else. The parts of the story where he expended energy and capital on things that were totally inconsequential to Vanguard’s success. 

But that’s the thing: When Bogle was undoubtedly having those human moments, he didn’t know what was going to move things forward and what wasn’t. He didn’t know what was going to provide the return. 

That’s because the plot points that don’t drive the narrative forward are usually omitted as the legend becomes streamlined and crystallized in the collective memory—it serves to create a world wherein we have this myopic, predictable understanding of how our renegade idols darted about the world, saw the clear path forward and did what nobody else dared to do. We oversimplify—and in the process, we forget that the mundane consistency of our day-to-day lives is often slowly weaving together our own narrative that we’ll someday reflect on and realize, “Oh, that’s how I got here.”

And we, too, will omit and gloss over the parts that don’t drive our personal narrative forward.

I noticed recently as I did a string of “Money with Katie” interviews that I was—unintentionally—creating this very sensible tale about how I got to where I am now. It’s the more exciting, edited version of the story, wherein I realized one random Tuesday that I wanted to change my life, and—in no short order—started a personal finance blog, grew that blog, and sold that blog to a larger organization, cashing in on a dream job and riches I never imagined when I graduated from college five years earlier with a degree in PR.

If only it were that simple, right?

If only it were that clear while we’re in it. 

That’s the “podcast version” of the Money with Katie story. The Guy Raz “How I Built This” narrative. 

Here’s what that story does not include:

• The phase between Corporate Barbie and Money with Katie where I thought I was going to become a full-time fitness instructor, so I went through hundreds of hours of training and taught hundreds of fitness classes. That meant approximately 200 mornings of waking up at 4:30 AM to teach a 45-minute class and 200 more evenings of rushing through traffic to teach a 5:30 PM class. Conservatively, I spent 1,000 hours learning how to be an instructor (and being an instructor). One-thousand hours!

• Not one, but two failed personal finance consulting businesses I ran (I started one, and joined a friend for the second) where the rates were an embarrassingly low sum, for hundreds (yes, hundreds) of one-on-one coaching sessions. 

• The countless amount of time I spent applying for jobs in 2020 when I was terrified I was going to lose mine, of which only two ever netted employment (my applications surely exceeded 50 per week at their peak).

• The five years I spent writing on my old blog that never made a single dollar or gained even a small semblance of the audience that Money with Katie has. Five years! That’s more than twice as long as I’ve been writing Money with Katie.

I realize I’m walking a thin line between the point I’m trying to make and the irritating, overdone “It TaKeS a LoT oF hArD wOrK” trope, so I’ll clarify where I’m going with this: 

So much (so much) of my time and effort from (a) the original realization I wanted to change my life and (b) where I am now was effectively wasted. “Wasted” in the sense that it didn’t culminate in anything impressive or noteworthy or lucrative, and also in the sense that I spent most of the weekends during those years very drunk. Coincidence? Probably not. #PartyWithKatie

And while I could sit here and make the case that each experience ended up netting something useful for my current endeavor (fitness = leadership and crowd presence and confidence, personal finance consulting = a rich repertoire of knowledge about what young women care about), that’d feel like a stretch.

But when I tell the story retroactively, I can neatly stitch the plot points together and narrate how they build so perfectly to create this obvious path to Money with Katie, but that’s only possible in retrospect. I had no idea what the fuck I was doing as I was doing it, and I’d venture a guess that most people who’ve built something they’re proud of would probably say the same. 

Unfortunately, we do others (and ourselves, frankly) a disservice when we refine the edges too much. We lull one another into this false state of assurance that when you’re doing the thing you’re supposed to be doing, you’ll know it—and you’ll know where to go, what to do, and how to do it. But that’s not how life actually works.

The reality of life is that it’s a little bit like buying an index fund (sorry, this is Money with Katie after all, a money metaphor had to be made). You’ll expend capital (read: energy) toward 1,000 different stocks (endeavors), and 912 of them will be total shit with low or no yield. 84 of them will do a little something, and the remaining four will be so successfully glorious that you’ll wonder how you didn’t see it in hindsight—it was so obvious, huh? Yeah. Not so much. 

Everyone swears in hindsight they could see the 2008 global financial crisis coming. Or that the 2020 market rally was predictable from all the stimulus. 

But if that many people really knew, there wouldn’t be a mere handful of people who became very wealthy from shorting the economy in 2008 (and even those clairvoyants haven’t done so well since then). 

It’s not that I think people are liars—just that we fool ourselves into thinking the “signs were there,” when in reality, we can only see the story clearly once it’s already happened. We forget about all the signs that pointed in the other direction and only remember the details that confirm the reality of what actually happened.

Our memories of our own lives are similar, and the way we memorialize epic people is, too. 

But that’s a mistake, because oftentimes the largest ROI comes from the work you don’t see. Day-to-day life and the thousands of small decisions we make every single day compound over time to slowly shape the directions our lives take. We can look back and identify those sliding-door moments, but while we’re in them, we have no idea they’re shaping our path. 

My favorite example of this in recent memory? After a few songs became major hits in 2019, Lizzo was asked in an interview what it felt like to be an “overnight success.” She was like, “Overnight success? Dude, I’ve been doing this for eight years.” 

ROI comes from the work you don’t see. “Gradually, then suddenly.”

A lot of our work (and capital) will be wasted. A lot of it won’t return anything useful or productive or valuable. We must become volume shooters in life and investing—invest our personal energy and capital early and often in a diverse set of opportunities to increase our chances of high returns. This probably looks like saying “yes” to things we aren’t sure about, investing  more than we think we need to, and not expecting phenomenal results most of the time. 

And when we get those high returns, we can look back and say, “I knew it.” 

This question comes up approximately once a week in my DMs, so I figured it was worthwhile to sit down and attempt to standardize my reply: When is it time to quit your “tradish” full-time gig and pursue your side hustle full-time?

To be fair, there are a lot of different takes on this; I know one gal who quit her full-time job before even starting her business because she felt like she was so stifled at work that she had no energy or creativity left over to build something in her free time (I pray that’s not your situation). 

My take, however, is that you shouldn’t leave a full-time job until your side hustle has proven long-term, consistent financial viability (sexy, right?). It may not be for everyone, but for the chronically pessimistic and risk-averse (hi, nice to meet you, kindred spirit), this is the only approach that I think works in all situations. 

(As in: You may decide to yeet full-time work with no plan and totally Zuckerberg it, but man, I’ll be damned if that’s not the exception.)

What do I mean by long-term, consistent financial viability?

Let’s take a walk down memory lane, shall we?

When I started Money with Katie, it didn’t make a single dime for about eight months. I just shouted into the void to an audience of seven people and texted my mom “please clap” every time I’d publish something. I don’t know of any side hustle that’s glamorous to start, but posting 60-second videos of yourself talking directly into the camera about a “really cool new blog post” you just wrote about Roth IRAs to three likes and zero comments certainly wasn’t all star power and rainbows for a long time. 

But during this period of void-shouting, I did a goal-setting workshop where I had to “examine my ideal life.” Unsurprisingly, I spent the majority of the meditation imagining myself as a resident of San Diego, living in an airy, white loft space filled with plants, and attending leisurely 9am yoga classes during the work week. And what was my source of income in this fantasy?

My ($0 in 2020 revenue) Money with Katie job. 

One of the questions I had to answer in the exercise post-meditation was about what amount of income would make me feel “safe.” I remember writing, “I want to make $10,000/month from Money with Katie. That would make me feel secure and successful.”

In retrospect, it’s pretty ambitious that I even wrote those words: I hadn’t made a single dollar from Money with Katie (and still was about 3 months away from monetization), and $10,000/mo. was roughly twice as much as I was earning in my day job that paid $60,000/year. A year!

(While my goals now are technically larger, they are—in some ways—less ambitious than that original $10,000/month goal, because now I have proof of concept. I had no idea what I was doing when I committed to $10,000/mo.)

The point is, even then, I knew that in order to leave my full-time job security, I’d need roughly twice as much income to feel safe doing it. 

Why? Because your corporate job offers a few things that doing it on your own likely doesn’t:

• 7.65% FICA tax, as opposed to the self-employment tax of 15.3% (in other words, your FICA liability doubles when you’re your own employer)

• Health insurance (this one can cost thousands of dollars per year, if not tens of thousands)

• 401(k) matches and bonuses/profit-sharing that can amount to thousands (again, if not tens of thousands)

• Paid time off (contrary to popular belief, being a business owner usually means taking less time off, not more; I still posted every day from my honeymoon for Money with Katie despite being “off” at my “real” job that week)

The TL;DR? You can’t just look at your base pay when you’re assessing how your side hustle income stacks up to your full-time job. 

(To be clear, I thought $10,000/mo. would make me feel totally comfortable leaving my full-time job—but $10,000 came and went. Then $20,000. Then $30,000. December 2021 revenue was more than $50,000, and I was still on the fence about whether or not it was safe to pursue full-time.)

The truth is: It’s a lot easier said than done to say goodbye to a biweekly paycheck, healthcare, and myriad other benefits, some of which are more personal than financial. I loved the people I worked with, too, and I knew Money with Katie meant working basically on my own. The last thing I wanted to do was isolate myself (especially after moving to Colorado, where I already didn’t know anybody). 

That’s why I tell other small business owners that—if they’re not sure when it’s time to leave their full-time job—to wait until it feels stupid to stay. I was approaching that point (where the ROI on the 40 hours per week I spent at work was so much lower than the ROI on the 30 hours I spent on Money with Katie) where it started to feel straight-up wasteful. 

But there was one other thing I wanted to prove, beyond a few fat sales months:

Consistency in income

The fact that some months I’d make $20,000 and other months I’d make $50,000 made it all feel really, really dicey—not because it wasn’t enough money, but because it felt so hard to predict. 

I did everything I could to manage cash flow and make it predictable—trying to plan sponsorships in three-month contracts, promote my products the same amount every month, etc., but I couldn’t deny that it felt a lot more unwieldy and random than I was prepared for. Moreover, my “high revenue” months were occurring during a wild bull market and economic boom times. I had no way of knowing if my business had staying power throughout recessions, wars, and long-term downturns. 

By the time I finally left, I had decided my threshold: If I could make $25,000/mo. for 6 months in a row in 2022, I would dip. That would be “proof of concept” enough for me that I could double my total corporate compensation (around $150,000 by this time) by going out on my own and do so consistently.  

So let’s recap quickly on the two main points I’d suggest to anyone facing the same dilemma:

• Your side hustle is reliably producing at least 2x your corporate income (salary, 401(k) match, bonuses, etc. included) 

• You’re producing that number (2x total compensation) for at least six months in a row

• You think that—by spending more time on your side hustle—you could scale it even larger

That last one’s important: If you can do your side hustle easily in your free time or semi-passively, there’s… potentially no reason to quit your job. I know everyone’s excited to ditch the 9–5 forever and never look back, but I think we under-appreciate the potential dopeness of full-time remote corporate work. 

Now, if your job is hella time-consuming, frustrating, or you just don’t like it, then that’s a different story—but if you enjoy what you’re doing full-time too and you don’t think you’ll gain any scalability benefits from spending more time on your side hustle, then I wouldn’t be so quick to assume you need to quit. 

Do you actually want to do the side hustle full-time?

The last exercise I’ll leave you with: Build out a fake calendar for yourself. A fake “week in the life” of running your side hustle as a full-time enterprise. 

Many full-timers-turned-solopreneurs I know are initially disoriented by dropping their full-time work, because it provides structure and scaffolding in our calendars that we can plan and plot around. Ever heard the saying, “If you want something done, give it to a busy person?” It’s a little bit like that.

Having more on your plate somehow forces your time management strategy to improve, and when you cut the corporate umbilical cord, things can feel aimless at first if you don’t already have a solid plan in place.

One such small business owner I spoke with a year ago told me the same: “I realized after quitting that I didn’t actually want to do this all day long. I missed my teammates at work, and I missed having somewhere to be in the morning. I found myself sleeping in too late, lacking motivation, and feeling generally lost, which I really wasn’t expecting.”

Hence the “week in the life” exercise. Sit down and plan: 

• What time will you wake up?

• What time will you start working?

• When will you take meetings?

• What time will you spend on pitching new business?

• What about time for actually running the business? Time for growth?

The time freedom is awesome, but a total lack of parameters is pretty horrifying—and it’s up to you to provide those for yourself (and hold yourself accountable to them). It’s not for everyone.

And as much as I wish I could tell you that all the female small business owners I know were set free when they broke out of their corporate shackles, it’s kinda the opposite: Most of them went through a rough transition period for six months to a year where they felt discombobulated, disconnected, and unsure of themselves, despite being certain they wanted to pursue their businesses full-time. 

That’s not to say you shouldn’t do it: Just expect it to be bumpy, and mitigate the bumps by planning ahead how you want your weeks and months to look. A good plan can—and will—remove a lot of the thrash.

How I actually ended up leaving

In the end, I took the easy way out and sold my business to a larger organization: It allowed me to keep my predictable biweekly paychecks, but share in the upside of Money with Katie’s potential growth. 

Other odds and ends

There are a few other things you’ll want to have in place before you go full-time in your side hustle to make it as seamless as possible, and the first is almost laughably practical:

• A bookkeeper.

Find a good accountant you trust. You cannot pay these people enough, I promise you. A good small business CPA is worth their weight in gold. Between keeping track of your expenses and revenue, filing your quarterly taxes for you, and letting you know if it’d be beneficial for you to change the structure of your organization, this is one thing I regret not investing in sooner. I mostly did this stuff myself and tapped my CPA when I had specific questions, but I wish I would’ve hired a bookkeeper to close the books for me every month and keep things on track.

• The other is a tangible goal. 

My goal for 2022 was (and is) $500,000 in personal take-home revenue. It’s up to you to decide what’s “enough.”

I’m big on setting ambitious goals that feel ridiculous, so maybe set one for yourself, but don’t overlook the “why.” In other words, maybe your goal isn’t $50,000 in monthly revenue working 40 hours a week. Maybe it’s $20,000 in monthly revenue working 15 hours a week. 

Deciding (a) how much you want to make and (b) how much you want to work helps ground your work ethic and—more importantly—ensure you’re operating at proper scale. If your goal is to make $50,000 a month working 40 hours a week and there’s a client who wants to pay you $500/mo. for five hours of your time, it might seem promising ($100/hour!), but that means you’re using 3% of your time to reach 1% of your goal. Not a great trade.

In conclusion

At the end of the day, I hate to say, “When you know, you know,” but I think it’s true: You’ll know when (or if) it’s time to pivot. By ensuring these benchmarks are met ahead of time, you’ll be ready to jump when it’s time: A good bookkeeper, six months of at least 2x revenue, and a plan for how you’ll spend your time. 

I talked on the podcast a few months ago about how the obsession with financial independence in America is a cry for help; in that podcast, I discussed the way in which people are working less because work is getting more demoralizing. I still think that’s true. 

But demonizing working harder (rather than acknowledging that, for some, it really is the answer to earning more and progressing faster) misses the point: Some people need true economic intervention and higher wages (approximately 53 million of them). 

Others—who want to earn $200,000/year and live the high life—are probably better candidates for introducing a little elbow grease to the equation and making some savvy business decisions. 

This is your brain on Late Stage Capitalism.