Stuff I’ve Learned About Running A Business — Lessons for Fellow and Aspiring Cubical Escapees

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This is the first issue of my newsletter, Stuff I’ve Learned about Running a Business. You can view a list of all published issues here.

It’s been 2.5 years since I went into business for myself.

2.5 years since my company was acquired and the new company said, “Thanks, but no thanks” to almost everyone who worked there.

2.5 years since I learned the hard way that even if you have meaningful equity, even if you’re really good at what you do, even if you worked really hard and contributed significantly to that company’s success, a startup’s obligations are not to you. They never were. A startup’s primary obligation is to ensure ROI for its investors, followed by a payout to its founders, followed, maybe, depending on your tax situation and if there’s anything left (there often isn’t, by this point) by a much, much smaller payout to everyone else.

I also learned that I didn’t want to be someone else’s employee anymore, and I would do whatever it took to make sure I didn’t have to.

If you, too, harbor dreams of escaping the corporate cubicle (or the startup open office) and starting your own business, here’s the most important thing I’ve learned: you have to want it more than you want to spend the foreseeable future feeling safe, secure and comfortable.

That’s what a job is. It’s a steady paycheck, whether you’ve had a productive week or been out with the flu (assuming you have paid sick leave, which is admittedly a big assumption). It’s work you already know how to do. It’s showing up and knowing what you need to get done each day.

When you start a business, all that goes out the window.

The Money Isn’t the Hardest Part

I found myself in a lot of challenging situations my first year, including but not limited to earning a lot less money, paying out the nose for crappy health insurance (I still have to do that, unfortunately), taking on clients that were a bad fit, and doing work that I didn’t enjoy.

The hardest part wasn’t the money itself. It was the constant feeling of not knowing what I was doing, not being able to predict my earnings, and all the fear and anxiety I had around those two specific things.

You have to want it more than you want to spend the foreseeable future feeling safe, secure and comfortable.

Until I started a business, I didn’t realize how much of my identity was invested in being a highly competent, high-earning, fancy-job-titled individual who pretty much had her shit together and knew what she was doing.

Overnight, I didn’t feel like that person anymore. I felt lost and terrified and confused and totally, hopelessly messy for a very long time. It sucked, and it was an absolutely necessary step on the path toward figuring what my business would be and who I would become within it.

Side note: If this is you right now, know that it does get better. The mess is uncomfortable, but it’s actually really important. You can’t have the “Eureka!” moment without a whole lot of mess first.

It’s not for Everyone (and That’s OK!)

Real talk: this shit is hard. It’s definitely not for everyone. And that’s OK! That’s the first thing I tell anyone who asks me about starting a business.

Some people thrive inside organizations. Others don’t have the stomach for the massive day-to-day uncertainty of being on their own or the desire to manage every aspect of a business. Financial considerations aside, not everyone has the temperament to make it work.

I didn’t realize how much of my identity was invested in being a highly competent, high-earning, fancy-job-titled individual who pretty much had her shit together and knew what she was doing.

But if you think you are cut out for running a business, if you want it so badly you can almost taste it, if you’re sure you were meant to be your own boss, I encourage you to ask yourself: do you want it more than you want to spend the foreseeable future feeling safe, secure and comfortable? If the answer is yes, why do you want it so badly?

Is the freedom and flexibility of self-employment worth the days when you stare at your computer and aren’t sure what to do? Is it worth hustling for new clients and not knowing what you’ll earn month-to-month? Is it worth a sky-high insurance premium that covers next to nothing (at least in the US)? Is it worth the risk that you may have to take whatever work you can get?

That’s the trade-off you’re facing. For me, it was worth it. SO worth it. It might be worth it for you, too, or it might not.

Real talk: this shit is hard. It’s definitely not for everyone. And that’s OK!

But I’ll tell you honestly, if you can’t answer, “Yes, it’s worth it!” to each of those questions, it will be very hard to keep going when things get tough (and they will). How they get tough will depend on your situation, but they will, at some point, get very, very tough. A key client will drop you. You’ll go weeks without earning anything. You’ll take on more than you can handle. You’ll burn yourself out and yearn for the predictability of a steady paycheck.

We all have rough patches. Remembering how much you want this life, and why you’ve chosen it, is the only way through.

Oh, and no matter what, be kind to yourself. This path is hard, and you’re incredibly brave for choosing it.

I write about radically ethical marketing, self-employment and non-sleazy self-promotion. Learn more at https://empoweredfreelancer.com/

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