Thinking of Leaving Your Job to Be Your Own Boss? Read this First

As told by someone who did just that 10 years ago.

You know the drill.

After high school, college. After college, a “good” job.

For me, it started with an internship that morphed into the full-time job I needed to pay off the student loans casting a shadow over my entire existence.

A decade or so after I graduated, if you took on student loans, the shadow became a tattoo.

After binge listening to “You can do it!” self-help tapes, I surprised myself and almost everyone who knew me by parlaying my first “real” job into a prestigious corporate gig followed by a series of wildest dream-fulfilling stints in Amsterdam, Paris, Sydney, Melbourne, and Tokyo.

Yes, it was amazing as it sounds. When I wasn’t traveling the world for work, I was taking friends on high-end vacations and paying for most of it with all the travel points I’d banked.

After about 15 years, I caught the plastic rabbit and asked, “Is this all there is?”

Little did I know that existential question was about to be T-boned by a global economic meltdown.

I pivoted before pivoting became trendy.

The economic implosion hastened my employer’s bankruptcy, and since my career was already in re-runs, I made the leap.

At 40, I proclaimed the second half of my career wouldn’t be characterized by waiting for someone else to deem me worthy of promotions and pay increases. I was going to be my own boss.

Cheery first-wave entrepreneurs — “influencers” hadn’t been invented yet — were just beginning to tout how easy it was to be your own boss and make millions. All while smiling over a MacBook and sipping coffee at an outdoor cafe. Conveniently, they sold the course that would show you the system and step-by-step plan that would make your new life “just add water” easy and chaos-free.

Sign me up! And I’ll have an espresso, please.

I took some courses, learned the systems, and felt prepared. And a few years later — yes, that’s right, years— I resigned from my high-paying, middle-prestige job on a sunny June day.

If corporate gave me a parting gift, it was the knowledge I could outwork almost anyone. I was confident that would be enough.

That was over ten years ago. Entrepreneurship and influencer life have caught fire since. Drop shipping, affiliate marketing, course creation, Etsy shops, and the whole internet proclaiming how easy it is to work a little and make a lot. Wealth porn settled in for a long winter’s nap.

Full disclosure: as of this writing, I’ve not hit millionaire status.

Selfies and influencers emerged in the early years of my entrepreneurship, and I saw a lot of fake private jet pictures and read endless memes reminding me, “She thought she could, and so she did!” It was a few years before the darker underside was exposed.

Now there are UN-fluencers making fun of wealth porn and calling out a new thing: perseverance porn. The “You can do it” and “Just don’t quit !” memes that sustained me in the early years are now the asbestos of entrepreneurship and labeled “toxic” positivity.

I have no regrets about leaving employment to be my own boss, yet there are a few things I wish I’d known ten years ago.

One of the most insidious illusions is equating spending money with progress.

Buying new equipment, setting up your social media, and paying for a new website is exciting and intoxicating, yet also misleading.

You feel like you’re on your way, investing in things you “have to have,” but you’re usually only depleting your accounts and replacing playing house with playing business but with real money. You’re convinced you “need” these bare necessities to be “legitimate.”

Often, this initial spending spree is a way to hide your fear.

There’s a lot you don’t know, and you imagine that will come with time, and in the meantime, you’ll get ready for that by spending. It’s seductive because it makes you feel in control. And in the early days, you usually have plenty of money.

Before you turn in your resignation or divest your 401k, see if your idea generates a profit in a small, sustainable way.

Does anyone other than your family and friends want your custom pickleball paddles, gourmet cupcakes, or vegan ice cream? If you make a profit, (and that’s a big “if”) take the next step.

No profits? Tune your offer before quitting your job, buying a ranch, and 100 emus.

You’ll still learn loads, and your mistakes won’t bankrupt you.

Running your own shop can be lonely.

You’re rarely alone as an employee, yet entrepreneurship can be isolating and lonely. Do anything you can to establish and maintain a peer group to get honest feedback and test ideas with others in the same boat.

The host at one conference ensured everyone was in a Mastermind group before leaving.

I walked away with a clique of other newbie entrepreneurs who offered invaluable been-there-done-that business insight and support. Find others who have walked the same path.

Ask yourself, “Am I just paying to be a part of something?”

The information in that $2000 course you “just have to have” is free at the local Small Business Development Center. But SBDCs aren’t Girl Boss sexy, so they’re easily overlooked. While that course creator your friend told you about is living your dream (allegedly). Just look at her sitting at that cafe table, crafting some brilliant email on her brilliant computer. Beware of that sizzle marketing and seductive spending. Don’t take the bait.

When I started, there was an SBDC within view of my apartment. Did I go and avail myself of all the offerings? Nope.

Check it out and save yourself lots of time and money. Mostly money.

Your business is not your baby.

A friend and his partner were investing their retirement money into a new business. One day, he confided,

“Since we don’t have children, this business is going to be our child.”

“Just make a big donation to charity and save yourself the heartache,” I quipped.

You’ve heard the old saying — loan money to a friend, lose your money, lose your friend.

Treat your business like your baby. Lose your retirement money and your partner.

If you make your business your child, you will hang on long after you should close it up. You’re more likely to make bad choices — ones you’d never make if you were running a business. When you make it your “baby,” you make it personal.

Don’t do it.

Plan for the end.

Judy Blume’s book “Forever” is a story of first love and first sex. I read it when I was a teenager.

What I remember most about the book is a question posed to one of the characters.

“Have you thought about how this relationship will end?”

Your first love and your first business have more in common than you think.

Plan for the end. Your energy will decline, your desires will change, and quitting is different when you’re the founder.

You can’t just walk away — and you might want to.

A friend of mine threw in the towel on her business. And a few years later, she paid thousands in tax penalties because she didn’t go through the steps to shut down her tax entity. In her mind, she quit. In the “mind” of the IRS, not so much.

Toxic positivity is real.

Anyone who tells you running your own business is a money tree surrounded by flowers of freedom and joy is likely trying to sell you something. Once you’ve bought their miracle framework, they’re in the wind, and you have to make it work. Read that again. If it were that easy to trade $2000 for $1 million, a lot more people would have done it.

Is life as an entrepreneur better than working for someone else? For me, that’s a “Hell Yes!” Yet, it’s not an easy money utopia. Starting a business is not for everyone, and when people don’t succeed, the successful, independent entrepreneur porn or perseverance porn shames them into silence, which means the very lessons learned that can help you make more informed choices never see the light of day.

There’s a secret, too.

Almost all the successful entrepreneurs I “looked up to” and, in part, modeled my new life after, I learned, shared one attribute: They were already rich.

And this fact was very carefully concealed behind thoughtfully crafted origin stories. Everyone loves the underdog who pulls themselves up by the bootstraps story, so that’s what they offered. They’d let out enough rope to tempt your aspirational appetite and not much more, but yeah, already rich.

And “rich” is a relative term, so it’s not hard to do “ethically.”

The thing about money is you always compare up. Someone who “only” owns a small house in the Hamptons might say, “We don’t own our own plane! We’re not rich.” But they have a lot more disposable income to hire coaches, designers, and help of all kinds. Most importantly, they have the space to make mistakes. And that makes a huge difference you may not factor into the equation.

In the last few years, fake bootstrapping is getting called out.

People who post online about buying their first house at 21, are getting called out for misleading people when the reality is their daddy bought them the house. People humble bragging about making $100k on their “First launch” usually omit they had plenty of money before they launched. Perhaps they don’t even think it matters, but $1k vs. $20k buy on Facebook advertising matters.

There’s nothing wrong with being rich. There’s nothing wrong with generational wealth, but wealth means you can afford to make mistakes.

Owning your own business can be a rewarding ride, but a business has a lot of dark corners people don’t talk about because any mistake or failure reflects back on you.

I hope you avoid these common gotchas, and please, if you have them, add your lessons learned in the comments.

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