The joys of self-employment: 7 reasons to love being your own boss


This is a significant marking point in my life. I have been self-employed for as long as I was employed, making it 12 years of each. From my first day of employment, I always knew that I would eventually work for myself. I was surprised that it took as long as it did to escape. In fact, when I was working in Tokyo for Thomson Financial in the early 1990s I had firm plans to resign and live in Hong Kong or Macau, working as a freelance journalist covering the region. Then a girlfriend and a series of promotions made me feel there was no rush to leave, and I ended up being transferred to London into a job as Global Director – Capital Markets. This gave me some great senior corporate experience that I would never have got if had gone solo earlier. However it didn’t take too long to reach the point when I was ready to resign and throw myself out into the Big Wide World. The day after I finished at Thomson in April 1996 I boarded a flight to Rio de Janeiro as the first stop on six months travels through the Americas. I had thought that as I traveled I’d think about what sort of business I’d start. I didn’t have time for that on my adventures, only seriously considering what I wanted to do once I arrived back in Sydney after six years overseas.

It was very tough going for a long time, particularly trying to build global work based out of Sydney, but the success of my books really made the difference, and just around now – after many years of hard slog – things are panning out the way I always envisioned. This suggests to me that they have a fair bit further to go yet – time will tell.

When I left work I was completely committed to working for myself and controlling my own destiny. From the beginning I didn’t ever consider taking external capital, because I felt it would make me beholden to someone else. In the near future I will be looking for external capital for a new venture, but it’s not one in which I will be a full-time executive. If I ever sell a company, I’m not going to with the company as part of the sale. When things were difficult for me in the early days, my worst nightmare was that I would have to get a job – that was something that I would do anything to avoid.

When I launched out on my own, I was thinking of writing a book on the joys of self-employment – why everybody should do it. The reality is that for many people, employment gives them what they want, including predictability of income (until you get laid off), the ability to do what you’re best at and not having to worry about other issues, and a consistent social environment.

But that’s not for me, and not for many other people, whether or not they’ve recognized it yet. Here are just a few reasons I love working for myself:

1. My life is completely free-form and open-ended. I can – and do – regularly wake up in the morning and decide to change what my business does and how I do it. If you are in a job – even if it’s as CEO – there are constraints and job definitions to work within.

2. I can be myself. My early experience of employment was trying hard to fit in to very particular corporate cultures. I later realized that it was not that I wasn’t suited to corporate or adult society per se, but that there simply wasn’t a fit between my personality and the companies I happened to be working in.

3. I get the value I create. If I do things well, I get the rewards for that – be they financial or otherwise. A key part of the trade-off of being employed is that you will only get a small proportion of the value you create for the organization.

4. I am ultimately far more secure than employees. While it’s a risk to set up a business venture or work for yourself, ultimately there is far greater security than working for a company or even government. I can’t be laid off, and while my income may vary, I can always make money. In addition the (potentially) greater rewards from self-employment provide a solid buffer.

5. I control my life. I choose where I live rather than living where I happen to find the right job, I sleep in, go to the beach during the day, work harder sometimes and slack off at others – all at my will and not having to ask for permission.

6. I am the only one that needs to believe in me. What I do and where I get to is not dependent on someone else recognizing my capabilities. While I did pretty well in my ‘corporate’ career, I don’t think anyone I reported to ever saw what I was truly capable of (something I am sure many people will have experienced), so I would have been limited by others’ perceptions.

7. I work to create results, not to impress others. The majority of employed people of all levels of seniority play political games, striving to be seen or to be liked by the right people, working in environments where perceptions very often trump capability and outcomes.

There are many more reasons. I’ll probably add to this list later – additions welcome!

7 replies
  1. Ross Dawson
    Ross Dawson says:

    My pleasure Elias! I’m biased here, but then again I’ve had reasonable exposure to both worlds and have a firm view on what works for me. The current trend to greater self-employment is part of increasing human emancipation.

  2. Mads Kristensen
    Mads Kristensen says:

    Great post on which I would like to add one thing that I think is missing: Acting on opportunity.
    One of the things I have found since going into self-employment 9 months ago is that there’s a lot more oppportunity in being self-employed. When you go about doing whatever you do, you meet people, share ideas and suddenly you’re presented with awsome opportunities that you wouldn’t otherwise have encountered in the corporate world. And even if you would, the whole corporate system would have made it difficult to act on them.
    This is not to say that one should act on all exciting opportunities coming ones way. In fact it seems like one of the pitfalls is to pick the right ones and not getting overwhelmed by them. But its just so much fun.
    If you’re the kind of person who usually play the role of hub in your network, being self-employed is where the real potential lies. It’s just amazing what you can get done and make happen even if you’re only yourself.

  3. Ross Dawson
    Ross Dawson says:

    That’s a great point Mads – I think that’s an eighth good reason. It’s been so long since I was employed that I forgot how constrained you are when you have ideas or possibilities come up. This relates to the point about my life being free-form and open-ended – that’s what enables you to take opportunities.
    I think similarly about this to you. Recently the way I have framed what I am trying to do is: create massive and diverse opportunities for myself, and take only the best. You have to leave many good opportunities to take the best ones. It is about creating choice, and then exercising that choice.

  4. Maria ODonovan
    Maria ODonovan says:

    Ross, I think you have been following your bliss.
    Joseph Campbell said it this way, in Power of Myth:
    “If you follow your bliss you put
    yourself on a kind of track that has been there all the while, waiting
    for you, and the life that you ought to be living is the one you are
    living. When you can see that, you begin to meet people who are in
    your field of bliss, and they open doors to you. I say, follow your
    bliss and don’t be afraid, and doors will open where you didn’t
    know they were going to be.”

  5. Irfan Asrar
    Irfan Asrar says:

    Hi Ross,
    I hope you remember me, I really enjoyed your latest post. Ironically I am now living and working in Tokyo thinking everyday that I am going to make the move back to working for myself and being self employed. Any way, I really found this post inspirational, please keep them coming.
    Irfan A

  6. Ross Dawson
    Ross Dawson says:

    Maria, I am an enormous fan of Joseph Campbell – yes absolutely that is a fabulous quote – thank you!
    Irfan, good to hear from you. Follow your path as and when it’s right – Maria’s quote above is perfect.

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