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?

And if you want to get first dibs on the upcoming Smart Exit Blueprint program, then hop on the list below and I’ll see you there:

  • Coach Comeback

    Having several tattoos myself I can say that comparison is pretty spot on lol!

    The 80/20 rule will serve you best: spend 20 % of the time planning and “thinking” about doing something and the other 80 taking action. You will make lots of mistakes… heavens knows I have…. but in the end, when you have developed such a compelling “why” you are doing it, no failure will be big enough to stop you from being a success at being your own boss!

    I especially love the one about not asking everybody and their mothers for advice. Most have and will never do what you are attempting so why ask them. TRUST, like Farnoosh says!


    • Farnoosh

      Coach Comeback, you have tattoos too? Am I the only one without them? ;)!
      Ah si si to the mistakes but that’s just part of the journey – when the “Why” becomes strong and rooted in the ground, nobody can throw you off. Thank you for sharing your brilliant thoughts…

  • Carmelo

    Hi Farnoosh! This post is so right on! But, what did I expect, huh? Thinking about that “freedom” word. I would agree completely. But, isn’t it all in the definition of the word? It’s not about freedom to goof off, avoid meetings, avoid responsibility, or any such non-sense as you underscored.

    It is about freedom to create, freedom to express yourself, freedom to work your own chosen hours on your own chosen projects. It is about no one telling you what to do or where to be or when to finish something or how it should look.

    And, as you said, you can’t go back, you just can’t. I’ve been self-employed in my own businesses for decades. There are so many reasons you can’t go back. How could you let some boss make you “wear those cheap clothes” that you let drop to the floor years ago? They’re tattered and stinky … ugh!

    Yet, it ain’t easy. There are bosses (your clients.) There are meetings (of some type.) There is responsibility. Decisions can’t be sloughed off onto someone else. But, it’s worth it if you’re predisposed to work and being autonomous.

    Can’t wait to see your next post! (I just have to hear your version of “it’s a blast!”) 😉

    • Farnoosh

      Oh dear, did I commit to doing that in the *next* post – I do believe I implied “future” version ;)! Hey Carmelo, I am really glad you brought up the other freedoms, those are so true. And I had no idea you’ve been on your own so long, what does it feel like over the years?
      Nobody said anything about easy, man! Easy is over-rated. Freedom is a beautiful prize that comes at a high cost, and that takes work, but work on our own terms. Stay with it and thanks for dropping by.

      • Carmelo

        Hmmm … well, okay, next part in the series. I’ll wait for it. 😉

        Gosh, Farnoosh. There have been many ups and downs and challenges galore! I “invented” a DYI home building course and company and putting all that together was the most challenging thing I’ve ever done. But, helping hundreds of people build their dream home? Wow. What a rush. Imagine the sense of accomplishment my clients had.

        Okay … back to my thousands of words …

  • Tess The Bold Life


    I always fantasized about the corporate world. I’m sure it was because I was a young mother with a completely different lifestyle. Except for two years after grad school I’ve always been self-employed. So I look at your photo and think lucky Farnoosh!

    I think your tips are excellent. I love how you keep it real. I see too many young people quit their jobs without a plan.

    • Farnoosh

      Tess, how interesting – you know, I bet if I hadn’t done it, I’d have died wondering so I am glad I did too. And there were some really really good, crazy, wild, awesome, fun times too. Japan was definitely one of them.
      Thank you for being my shining cheer leader. You are a gem, Tess, just as you are, bold and beautiful.

  • Bruce Rodgers

    Dear Farnoosh, I believe you wrote this brilliant article for me!

    As you know, this has indeed pretty much mirrored my steps over the last 6 months in my transition from Corporate to Self-Employment. This article lines out SO many of the things that I have encountered – and in many cases never expected, including both the relief and fear that comes leaving a soul-sucking corporate job.

    Sure, the money in Corporate is great – who can deny that? BUT ironically, for me, it really came at a much GREATER COST – to my health, my mind, my very life. And my belief now is that in time, I will far surpass that “comfy salary”….

    For me now, it’s all about taking ownership – of the decisions, directions, the successes AND the failures… and honestly, for me, these are the things that truly make me feel ALIVE.

    It’s not always easy… but it IS mine.

    I think I will print this one out, frame it, and put it on my office wall. (Right next to my whiteboard … 😉 What inspiration!

    Simply put: Thank you.


    • Farnoosh

      Of course I wrote it for you, Bruce! These things we encounter on our own are the hardest parts of adjustment, because excitement overtakes the reality when we are giving up the other boss ;)! But you aren’t alone – I have felt and gone through all of it too, Bruce.
      Hey, the money at self-employment is gonna be GREATER – you’ll make that corporate paycheck look *small* if you stay determined. Stay inspired, and great things will come. Thanks for walking your path, Bruce. One more role models for others to look to.

  • Clay

    I can totally relate to my experience. I left the corporate world to become my own boss, and I had to realize the drawbacks after dreaming about the freedom and positive sides. Yet, I’m still convinced it was definitely worth it!

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  • Etienne Do

    Greart article