A guy walks into a bar. Seated on a barstool is another guy around his age. The first guy sits down and they get to talking.
“I’m miserable at my job,” the second guy says. “I’m undervalued and under-appreciated. I’ve been promised a promotion for two years now that hasn’t happened. And for years, my raises haven’t even kept up with inflation.”
“Same here,” says the first guy, sipping his beer.
“Oh well, what can you do about it?” the second guy says, sulking.
“Well, I’m building my business on the side,” says the first guy. “I still need the paycheck from the main gig, but I’ve been getting a lot done in the nights and mornings on the new thing. It doesn’t look like a lot of progress day-to-day, but I’ve been at it a year now, and things are finally starting to move.”
“Must be nice,” says the second guy. “I have a wife and kids. I don’t have that kind of time.”
“I have a wife and little kids, too. But I make the time. Usually before the house wakes up.”
“Aren’t you worried about losing the comfortable paycheck?” the second guy asks.
The first guy shrugs. “That’s out of my control. They could lay me off or re-org and boot me out at any time. It’s not like it’s the safe path anymore.”
They sit in silence for a few beats before the second guy chuckles and shakes his head.
“Starting a company while working a full-time gig with a wife and kids. That’s crazy.”
The first guy finishes his drink and looks up with a grim smile.
“Buddy, not building something of your own is the crazy move.”
THE MACHINERY
Familiarity and safety are not the same thing.
Your job feels safe right now because it’s familiar. You know who to bug to get your expense reports approved. You have relationships with key players around the business. You get “unlimited” PTO (and you even occasionally take some time off).
But you’re familiar with a system that can cut you in an afternoon. Just because you know how the machine works doesn’t mean you’re the one at the controls.
I’ve spent nearly two decades selling corporate jobs to people at all levels. Entry-level kids, rising stars, heavy-hitting leaders, C-suite executives.
I architect the early stages of the corporate relationship. The best weeks and months you’ll ever have: when your partner wants to spend all their time with you, when everything feels exciting, when the sex is the best it’s ever gonna be.
But like all relationships, the honeymoon period fades. Reality sets in. If you’re not a good fit, things sour within a few months. One of you gets dissatisfied and decides to move on.
And if you are a good fit? If you become one of the people who are “indispensable”?
You get more work.
A former executive I worked with referred to it as “winning a pie-eating contest where the reward is more pie.”
High performers don’t get more freedom or autonomy. They get the work of the people who can’t do theirs, plus a little more money (on a relative scale).
Oh, and perceived status. Can’t forget about that.
And that last bit plays a big role in why we stay. The brain treats the current situation as a reference point and any deviation as a potential loss. Plus, wanting more feels like betrayal of the people who depend on us.
Can you really picture yourself leaving the boss who gave you your first big promotion?
Or saying goodbye to the team that’s had your back through vacations, illnesses, or major life events like having kids or losing parents?
You’re not broken because you think this way. There are three main forces, all combining to form a mechanism that keeps you in place:
Humans have a status quo bias. We stick to whatever we’re already doing, even when the cost of switching is small and the alternative is objectively better. The same brain that doesn’t send the meal back when the order’s wrong keeps you in a job that’s going nowhere.
We’re loss-aversion creatures. Psychologically speaking, the pain of losing what you have is twice as powerful as the pleasure of gaining something better. That means your brain treats your current job as worth double its actual value, because losing it would hit you twice as hard.
We’ve all accepted the gratitude gag order: the idea that our lives are already subjectively better than most lives throughout human history, so it’s ungrateful to want more.
What does that add up to? When you think about leaving, you feel like an asshole for wanting out. Plus the paycheck is good, so the idea of quitting and going all in is scary.
And therein lies the rub.
BOTH ARE TRUE
“Quit and go all-in” or “stay and be grateful.”
Those are the two options on the table. They’re the only ones we seem to hear about, anyway.
The “quit” crowd is selling a dream that requires a fallback plan.
What happens if you flop in spectacular fashion (which, by the way, is what happens to most entrepreneurs)? How does your mortgage get paid? What are your kids eating?
The other camp is more crowded: it’s the “stay” crowd. Where your well-meaning friends and family sit. The ones who feel the need to warn you against taking a risk.
“Things are good as they are...why rock the boat?”
“What happens if your boss sees those posts?”
“You know most small businesses fail, right?”
Ok, so the quit crowd is a pipe dream, and the stay crowd makes leaving look like an apocalyptic event. What are you supposed to do?
Stay AND build.
Keep bringing in cash flow from your day job and build your future in the margins (nights, weekends, etc.). Use the money you make from your paycheck to fund your 2nd act.
Because both can be true. You can like your job, and know that it’s not the thing you want to be doing a decade from now.
You can love your team, and believe that most of them will still take your calls when you become a free agent.
There’s even a scenario where your boss takes a little bit of credit for developing you into the kind of person willing to bet on himself.
On top of that, the day job can actually improve your side hustle. And vice versa.
Take my thing as an example. I’m coaching people through their career transitions (something I’ve done for almost 20 years) AND coaching people through the transformation from employee to founder (something I’m doing right now, as I write this). I’m making content to start getting known for something slightly different from what my LinkedIn says about me.
And guess what? Making content means you have to understand how to capture and keep attention. You have to get to the point. You need to tell better stories. You have to make your ideas easy to understand.
You know who benefits from my improving skills?
My team. My bosses. My company.
My emails are clearer. My presentations are more engaging. My strategic thinking better incorporates second and third-order consequences. My project management skills have improved from dubious to decent, and my efficiency at work has gone up as I get more efficient in my side hustle.
On the flip side, I’m better at analyzing data, making decisions, negotiating, and managing relationships, thanks to the hours I’m clocking into the day job. I bring skills I’ve cultivated in my corporate life for decades into my own company.
Don’t just quit. Don’t just stay, either.
Do both.
I know what you’re thinking:
“How, exactly?”
STEP 1: START BEFORE YOU’RE READY
This idea of building while employed isn’t new.
But there’s a mistake almost everyone makes. It’s one word that can cost you anywhere from days to years.
Research.
Yes, when you’re brand new at something, you need to at least make yourself functional. That means you’re going to have to read a few books or take a couple of courses.
But a lot of people wait to start until they finish their “research.”
Which can keep pushing back that start date further and further on the calendar.
Do both. Read AND apply. Take courses AND test your thesis in real time.
Let the books and courses get you functional, then get moving. Once you’re doing the thing, you learn way more from taking action than you will from anything secondhand. Getting reps and at-bats gives you those real lessons (the ones that sting).
Nobody ever got a bloody nose watching a tutorial.
STEP 2: STEAL TIME
Ok, so you’re not going to let research slow you down. You’re ready to build while you’re learning.
But you have a full-time gig, a spouse, kids, and after-school activities. Zero free time on the schedule.
How are you supposed to make time for your build?
You don’t make it. You steal it.
This isn’t a “one big bank heist and I retire to a non-extradition country” type of theft. The time you’re stealing looks more like picking pockets, or palming something from a corner store. A bunch of small transactions that add up over time.
And who’s the first mark?
You are.
Your routines. Your lifestyle. Your down time. Compare how you spend your time with the hours you’ll need to build. You’ll find wasted time everywhere.
The highest-leverage move you can make is to create 60-90 minutes, either late at night or early in the morning. I call these my “Sacred Hours,” the hours every week where nobody else needs me. These are for deep work.
After that, it’s wherever you can find it. An afternoon where a meeting was canceled, sitting in the school pick-up line, an hour on the couch with a laptop or a notebook instead of doomscrolling.
90 minutes a day doesn’t sound like a lot. But if you’re working 5-day weeks, it becomes 7.5 hours a week. Do that every week for a year, and you have 10 full 40-hour weeks.
Do you think you could get a solopreneur business off the ground with more than two months of dedicated effort?
To quote Walter White, “You’re goddamn right.”
Your writing content is definitely improving in style and in general. This was a good post. As always there is some nugget of value to glean to keep me going in my own journey.
That title alone says a lot. I’ve been on the hiring side and the recruiting side, and the trust gap is real. A lot of it comes from incentives, recruiters get paid to fill a role, not to find you the right one. Worth remembering when you’re job hunting.