From Corporate to Self-Employed: How to Adjust to Being Your Own Boss

Maybe You Weren’t Meant to Have a Boss!

“You weren’t meant to have a boss!” wrote Paul Graham on his blog in 2008.

It’s a popular piece that taps into the psychology of whether we as human beings are meant to have bosses. It’s a wild article. He compares us to lions in Africa, then weaves in our attachment to junk food and the unnatural way we have to act in large companies and concludes with the crazy notion that perhaps some of us were simply not meant to have a boss!

And Paul may deny this because, well, he has never heard of me but he wrote that piece for me. With one headline, he unglued my long corporate career and all my sorry ambitions around becoming an executive in a Fortune 100 company. In one instant, my mind let go of a 12-year pursuit for something I didn’t even want anymore … letting it fall from my body to the floor like cheap clothing that I will never wear again.

At some point in your career, you may wonder if you were meant to have a boss and maybe – just maybe – you might want to venture out on your own if only for a little while. You might want to trade your boss and employment for working for yourself.

I say go for it. Don’t be so terrified of the call to self-employment. It’s normal. It’s OK. It’s not as radical as you may think. If your heart is calling you to do something else and won’t shut up about it, you might want to take a listen, but pay attention to the transition because going from having a boss to being a boss is surprisingly overwhelming in a subtle, strange, and counter-intuitive kinda way.

I’ve had lots of bosses, from horrid to great bosses, and then one faithful day, I’d had enough, I had spent too long managing my bosses, and much too long suppressing my cry for independence. I was most definitely not meant to have a boss. Ever! The only choice was to become my own boss.

Now, I work with clients that are making this drastic shift from corporate to self-employment and we all agree that the transition to becoming your own boss is not to be taken lightly.

Freedom is one word that comes to mind when you tell someone you are quitting to go start your own gig. “Ah you’ll be so free, free as a bird, no boss, no structure, no hierarchy, no meetings!”, they say. Who knows what they are thinking, probably a more ignorant version of this.

And that’s totally rubbish. You don’t exactly quit to goof off in your backyard all day or play on your computer all night. You can do that at your corporate job, more or less, if you find the right place!

Nah, you quit your day job so you REALLY start working and you stop wasting time doing the things that you do not want to do.

You quit your job so you bust your chops to make a business out of your ideas. You quit so you make a living on your own terms, and to make a difference with your work in the world.

You quit so you call the shots but then you have to deliver on the shots and answer to yourself when the shots were wrong and you didn’t know better. You also pay the price for the wrong shots and get to make them again, hopefully better than last time.

You quit because you exchange a soul-sucking job as one of my clients calls it for a higher quality of work that comes with exhaustion and sacrifice and constant renewal of commitment even if the rewards are higher.

Freedom then is not an automatic condition; it is a privilege that you have to earn with your self-discipline and your never-ending devotion to success. Success requires a mindset, a structure, accountability and results.

Going from Corporate to Self-Employed: 7 Useful Truths

Now how do you adjust to being your own boss without driving yourself and everyone around you crazy?

Listen, if I haven’t said it enough, being my own boss and calling my own shots has been the greatest decision of my life, right up there with marrying my soul-mate in case he reads this piece ;)! But there are a few things I wish I had known before I took this journey.

Here’s 7 useful truths if you are considering the route to self-employment.

You need to shift your perspective: No more relying on company salary. No more lolly gagging your days away. No more blaming anyone, and that includes the economy, the state of the world and your parents. No more. You have got to shift your perspective in order to crush it in your business.

You have to be willing to make decisions on your own: No more letting others tell you what you can or cannot or should and should not do. No more asking around to make sure everyone approves. Have a mentor or an expert or an adviser to consult with and someone who supports you fiercely, such as a life partner. And commit to decisions. Commit to action.

You have to be OK with taking risks: No more keeping it all safe and measured. No more standing on the sidelines watching others go by and saying ‘Oh I wish I was doing that but I just don’t have the guts!’ You need guts to start a business. If you don’t have guts, get some or get out of the game.

You must figure out a way to deal with failure: No more fooling yourself that you will make it the first time. No more being deadly afraid of failing. Embrace it and get over it. Fail fast. Fail often. Fail forward. Get it done with and move on your success.

You have to have your own back: You boss is not going to bat for you anyway. You go to bat for you. And it’s not the upper management of some company that you are begging for that overdue promo anymore. It’s the whole world that you target now to find your place in it, to offer your gifts and services and products, and to watch out for the missteps. You have your own back.

You must cross the point of no return: You can’t go back to having a boss. Once your own boss, always your own boss. Maybe you find that radical. We can talk in 20 years and see if I’ve changed my mind but that’s the truth for me and for every entrepreneur I have met or read or heard. So this is the point of no-return. It’s like getting a tattoo (ouch). It’s permanent, it’s forever, and taking it off is a big mess so one must approach the decision with much care and forethought. And in a completely sober state.

You must trust yourself: Have a little – or a LOT of confidence in yourself. Trust yourself more than you trust others. Trust your gut, your intuition, your inner voice. Trust your heart when it tells you to do something. Trust your brain to make smart choices. And trust the fear because it is sometimes there to tell you that you are stepping out of that comfort zone, finally, and that fear is part of the game, and if it weren’t fearful, well then, you’d have a lot of company over here doing the courageous thing you are doing: going from corporate to self-employed. But it takes a special person to make this leap. And you are that person.

So trust your amazing, authentic, and incredible self and please give that self a chance. A full unadulterated untainted unblemished chance.

Don’t worry. I am focusing on the hard stuff because you need to be aware of the sacrifices you have to make and of the changes you need to embrace before you can fully enjoy self-employment. Next part in this series will focus on the blast you are going to have when you are your own boss.

Until then, leave me your comments about your state of work: are you employed or at corporate?