4 Ways Self-Employment Is Less Risky than Getting a Job

Hand gripping another hand on a cliff edgeModern society has conditioned us to believe that having a job is the safe route; that the artist’s or entrepreneur’s life is only for those fearless few who don’t mind the risks.


Artists know that creation-as-business is more rewarding than playing cog in someone else’s machine. And I’d like to show you four ways self-employment reduces your risk.

I’ll say it plain: making your own way is the safe route.

Not that you’ll hear this in the voices around you… Your mother wonders when you’re finally going to get a real job. Friends ask if you’ve “gotten it out of your system.”

Even you sometimes wonder whether it wouldn’t be safer to take the well-traveled road.

I say again, vehemently: no, it would not.

1. Taking control over your own happiness

First, by spending 40 or more hours a week at someone else’s beck and call you will sacrifice control over your own happiness. I direct your attention to everyone’s favorite unpronouncable name:

Because for most of us a job is such a central part of life, it is essential that this activity be as enjoyable and rewarding as possible. Yet many people feel that as long as they get decent pay and some security, it does not matter how boring or alienating their job is. Such an attitude, however, amounts to throwing away almost 40 percent of one’s waking life. And since no one else is going to take the trouble of making sure that we enjoy our work, it makes sense for each of us to take on this responsibility.

Finding Flow: The Psychology of Engagement with Everyday Life by Mihaly Csikszentmihalyi, p. 101-2; emphasis mine.

Working for someone else gives them final say over what you do, how you do it, when you do it, and who you do it with and for. Surrendering those autonomies is tantamount to surrending control over your own happiness.

An obvious point, perhaps, but one it’s easy to forget when bills come due.

That brings up our second point.

2. Jobs have nothing to do with financial security

Once upon a time perhaps they did, but it’s no longer the case. We’ve all formed a conspiracy of silence to fool ourselves.

Sure, income may be tight for the artist. For the suddenly-unemployed, income is nonexistent – usually with no warning, because your employer, not you, decides whether you remain employed.

Oh; if you had a job for a few years, you could live on your savings for a while? If you’ve seen statistics on who is saving, and how much, you know that’s not generally true.

3. You escape from the hedonic treadmill

One reason even those with well-paying jobs fail to save is the hedonic treadmill. Here’s a third risk you’ll reduce by working for yourself…

The longer and more frequently we engage in an activity, the less pleasure we get from the activity and the more intensity it takes to achieve the same level of pleasure.

Materialism is designed to put you on the hedonic treadmill. This month’s nice restaurant isn’t quite as nice after while, because you’ve seen the ads for nicer places. A three-year-old car seems old. A week in Vail is replaced by a week in Gstaadt. A subscription to the gym gives way to a personal trainer.

None of this stuff is bad if you can afford it. That’s the problem: you can afford it, so you do. Why would anyone live without the nice things you work your head to the bone to have?

And there you are, on the hedonic treadmill, always needing more because enough is never enough.

Bear in mind that it’s not the selfish or materialistic who have this tendency. If you’re human, you suffer entropy of satisfaction: what thrilled yesterday pleases today and bores tomorrow. It takes marvelous self-control and dedication to avoid getting sucked into the lifestyle promoted by the marketing machine’s endless barrage.

Few entrepreneurs have a steady, regular cash flow. Most have ups and downs. It’s always a juggling act, dividing time between doing business and working on the business. Spend time marketing and work slows down. Then the marketing starts to have an effect and work picks up, so you have less time for marketing. You take a vacation, and have to find a way to earn the money beforehand for both the vacation costs and the lost income while you’re away from the business.

Constant focus makes complacency less of a danger. When your cash flow fluctuates (within acceptable limits) you’re less inclined to live at the higher limit all the time when you can find ways to budget to the lower limit. With planning, this automatically creates a savings account to help when life breaks out of the limits.

4. Placing a greater value on your own time and effort

A fourth, closely related risk: forgetting the connection between money spent and the time and effort it took to earn it.

Taking greater control to manage your own life is a huge step off the hedonic treadmill. The connection between money and the time and effort it takes to earn it is far more tangible. Dinner out is no longer a slide of the credit card, it’s 3 or 4 hours of work. It may well be worth it, but being more aware of the connection means you’ll stop and think.

We all know people who’ve mentally and practically lost the connection between hours spent working and the cost of fun.

Some of the power of the hedonic treadmill is thrill-seeking. Most of us live to some degree, as the poet said, lives of quiet desperation. While desperation may be too strong a word, think back to the last time your life was truly thrilling without a huge price tag. For many people, their memory doesn’t go back that far. The daily grind seems to grind away life’s edges, nudging us to go find edges which still challenge.

We need excitement in life. The entrepreneur’s life includes it by default. A more visceral and immediate lifestyle reduces your risks and increases your rewards.

Hanging on with your own hands

Picture this scene: walking along a mountain path, you slip – and go right over the edge. Your hired guide grabs your hand. Whew! Safety.

Then, he starts to slip…

Look into his eyes. Imagine it. This is no lifelong friend, no loved one, no trusted ally. Your only relationship is money.

When he starts to slip, would you rather be hanging from his hand, or hanging onto something with your own?

Despite the fact that I’m a bit of a control freak, it took me over 25 years to learn the lesson that working for me carries less risk and more reward than working for anyone else.

I want others to learn that lesson without waiting 25 years.

Over to you

Does a job really play such a large role in the pursuit of happiness?

Does the hedonic treadmill affect your finances?

If you currently have a job, do you depend on it, or do you believe it’s a calculated risk?

About the author: He may have taken a knock to the noggin in his leap off the hedonic treadmill, but Joel D Canfield still manages to string sentences together most days. Though he pays the bills as a web developer (self-employed, of course) he’s managed to write and self-publish his 10th book, released this month. Its cheeky title is You Don’t Want a Job and he believes every word of it.

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Responses to this Post


  1. As somebody who has a blog called the Skool of Life and been through more than my fair share of jobs I’ve hated, I would have to completely agree. Years ago there was this mindset that a job was a guarantee of financial security. But that myth got dispelled when 1000’s of people lost their jobs over the last few years. I went to business school and I have friends who have struggled just to get back to what they were making before business school. While self employment may not be pay as much in the short term, I think that people who stick it out are rewarded for sticking it out .

    I recently interviewed Cameron Herold and one of the things he said to me that really stood out was that in a job “vision is decided for you.” You’re essentially executing somebody else’s master plan. That’s when I knew that ultimately if I did have a job it would be nothing but a stepping stone to full time self employment. Thanks for the great post.

    • Srinivas, that’s a great quote from Herold.

      As you point out, if we focus on money, we might not make the best long-term choices. It’s like all those companies who’ve shortened their financial plan from 5 years to 3 months so they can keep looking good on Wall Street.

      A job is short-term thinking, and I worry that folks won’t realize it until they’ve been hurt by it.

  2. I chose self-employment mainly because I wanted to be able to work from home when my kids were young. Well, they’re mostly grown up now and I am so grateful to them for inspiring me to do this.

    Working for myself is WAY better than a regular job. I set my own hours. I work at times that suit me best on any particular day. If I really hate doing something (like bookkeeping, for example) I outsource it.

    I think I work HARDER working for myself — and getting ready to take a vacation is always stressful (because there’s no one to do my work when I’m away) — but I am so happy I am doing this.

    But here’s the funny thing: I was a newspaper editor before (now I’m a writing coach). If I had stuck with my job, I would likely be out of work right now! So glad I made this decision 18 years ago.

    • Daphne, the one single goal of my book is my fervent hope that people will make the choice before it’s made for them. Simply delighted that you leapt instead of being pushed.

      Your comment sounds like my entire business philosophy, summarized.

      Best Beloved and I can’t imagine going off to a job and leaving our Little One in someone else’s care. Her entire life, we’ve worked from home, here with her all the time, and I can’t imagine any other life.

      Vacations: have you tried to find a vacation trade partner? If you do it right, you can find someone who’ll put out fires for you while you’re gone if you’ll do the same for them. Doesn’t have to mean taking on a second job for two weeks, but just knowing a trusted partner is there to care for your precious clients can make time away much more relaxing.

  3. Your post reminded me of someone saying that if you don’t start building your dreams, someone will hire you to build theirs. Sadly, unlearning the so-called myths of employment ingrained in us through generations is a slow, painstaking process. Perhaps, it’s easier to slave your time away working for someone than being accountable for your very own success and happiness. I guess, only a few brave soul are willing to make a world of difference in such a short lifetime.

    • Shaleen, it is certainly easier. But as you suggest, easy is hardly a good measuring stick, is it?

      Though jobs are only as old as the industrial revolution, we’ve had a handful of generations to teach ourselves that they’re the safe option. I’m hoping we can get back to something more sensible within a generation or two.

      I certainly know MY little girl will never have a job. She’s already planning all the businesses she’s going to operate.

  4. Another great passionate post Mark. 100% agree. Very much enjoyed Joel’s choice of words “vehemently”. I am completely sold on the self employed route and thanks for all the coaching advice you’ve given me so far. Extremely helpful. Just sold another abstract painting yesterday that will pay for my holiday. Love your work and so thankful to have found you online.

    • Congrats on the painting sale! I’m sure it will make the holiday all the more enjoyable to know your Muse is footing the bill. 🙂

      Joel takes the credit for this post, but you won’t be surprised to hear he’s articulated some of my own vehemently held beliefs!

    • Thanks so much, Simon. I don’t do things by halves, so I feel vehement far more than I actually say it.

      So, working with Mark, you’ve reached the point you can pay for holiday by selling art? I’d love to chat about that further. I have some case studies in my book, provided by friends, but I’d love to gather more from people who are making a success in unorthodox self-employment (and art seems to be the most unexpected place, to most folks I speak with.)

      A quick glance at your website has me intrigued.

      • Would love to talk more with you about your book Joel. Yes, the art world is a little unorthodox. So are the artists! I really connect with your post, it’s so refreshing to hear like minded people express themselves with such conviction. People’s happiness and creative freedom at work is the highest priority. Only then will profits and productivity levels rise.

        • I’m part of a worldwide community of songwriters. Talk about, erm, shall we say, eclectic? I’d like to send you a few questions by email if that’s okay.

  5. Number 3 can possibly make one a better person. 🙂

    • A nice side-effect. 🙂

    • My comment seems to have disappeared. (Or my brain. Could be my brain.)

      Yes, since I’ve chosen a simpler life I’ve had more time to help others. As Best Beloved and I work together to keep the onslaught of materialism in check and set a good example for our daughter, it becomes easier to project our beliefs about generosity and connectedness.

  6. I’ve definitely experienced the fact of no.2! We think jobs give us security, but it is definitely an illusion! One day you can think you’re secure in a job and the next day the GFC happens and you’re packing your bags wondering how you didn’t see this coming!

    I love spending my time on things that matter to me and make a difference in people’s lives – so I’m all for this! Thanks for writing this post

    One question: what advice would you give people in managing their anxiety when money does go down in the inevitably up and down cycle for entrepreneurs?

    Thanks in advance!

    • Kerri, take another look at #3, getting off the hedonic treadmill.

      I know, from my travels and my international friendships, that my bare-bones lifestyle is a rare exception. Most people in anywhere but the poorest nations have a large margin of luxury around their core needs.

      Living simply is the single best defense against money worries. It’s not about money itself, about the bills or cost of living. It’s about taking control, knowing how very little you can get by with and still be happy.

      Facing fears head on is vital. When something is a vague shadow in a darkened room, we amplify it into a monster. If we’ll just switch on a light and look at it, it usually turns out to be a pair of jeans over a chair.

      Consider what you’re afraid of, in those downturns.

      Are you afraid of starving to death?

      Are you afraid of losing your home?

      Are you afraid of wearing rags?

      Probably not. Your fears are probably vague images of “not enough”–which, when you shine a light on them, don’t mean much 😉

      Do this exercise: take 3 cards. On one, write the worst case scenario. Not the nukes-and-asteroids worst case, but the worst realistic case.

      On another, write down the best case, what could really happen and be really great.

      On the third, write down what you think is the most likely thing. Honestly.

      Put “worst” on the left edge of the table or desk. Put “best” on the right edge.

      Put “realistic” between them, in the position you think it really occupies.

      Is it waaaaay over by worst, or is it within comfortable distance of best?

      I’ve written a bunch about facing fears and taking control. If you’d like more info, I’d love to chat.

      Gorgeous lush website, by the way. As a web designer, I really appreciate that.

  7. I wouldn’t say that there is any way of being self-employment without cutting the chances of being self-employed. Reducing risk always includes reducing chances/return. Sadly…

    • I can’t agree, Ulrich.

      Doesn’t moving from a mountain trail to a meadow path reduce risk?

      Doesn’t eating better and getting exercise reduce risk?

      It’s not a zero-sum game.

      But, even if we pretend the risks are the same, the rewards are NOT the same. Either way, isn’t having control better than surrendering control?

  8. I’d say the number one reason is it forces you to learn to sell and communicate effectively, often through speaking and writing. It builds that “people skill” which builds rapport and relationships.

    • Many workers are insulated from customer contact, and many businesses seem to foster less-than-professional interaction within themselves. That won’t work as an entrepreneur or freelancer.

      I just finished Rohit Bhargava’s “Likeonomics” which shared research showing that when people have a choice, they’ll work with someone less skilled but more likeable rather than someone more skilled but less likeable.

  9. What an awesome pick-me-up! I decided to become self-employed last year, and it was the most liberating decision that I had ever made. I’m a creative freelancer and musician, and admittedly, it gets really tough sometimes. I love it! But it can be tough – so much that I attempted the dreaded job search again. And that quickly reminded me why I decided to forgo it all in the first place. Reading this article helped to further solidify my decision, and it couldn’t have come to me at a better time. I’ll keep at it and keep on pushing. Thank you so much!

    • So glad you got something from the article. I’ve also had times when I despaired of ever making it, but a job search tells you pretty quickly why you chose this path.

      It’s not a fast process, but neither is growing an oak tree or learning to play the violin or raising a child. All very worthwhile, though, and not *despite* the time, but often, *because* of it.

      How can I help you stay on top, stay focused, stay moving? I want you to win, Nneka. It’s important.

      • “a job search tells you pretty quickly why you chose this path.”

        It certainly does! Couldn’t agree more. I’m one of those talked about “new grads” – though it’s been 3 years – and after getting fed up with the job search hamster wheel early last year, I decided to take matters into my own hands. Best decision I’ve ever made! I knew it would be hard work, which I was well-prepared for, but it’s having to deal with outside pressure from my family and those around me to “get a job” – as if I wasn’t trying before. I tune them out about 80% of the time, but the other 20% consists of me wishing for financial independence and/or a job, just so they can leave me alone. I still live with my family, as my meagre income can’t afford rent. On the other hand, I strongly dislike the concept of jobs for pretty much all of the reasons that you listed. I want a job because of the “instant” money, but I hate the bureaucracy of the corporate world and its hiring process. So I’m stuck. It’s a bit of an uncomfortable situation – but I’m learning everyday and picking up new skills along the way. I’ve learned much more about the “real world” in the past year than I had in all 6 years of university, that’s for sure.

        Didn’t mean to rant, there! But I think what I need the most is probably some perspective. I’ve constantly got my eye on the prize, trained so far ahead, that I forget where I’m standing, so to speak. I should pay attention to my current situation, as well, and find coping mechanisms, along with researching new ways of building my client base and navigating the creative field. It’s competitive – but I see that as a good thing. It means that more people are being courageous enough to use their talents, as opposed to hiding them away. And that’s encouraging.

        Thanks again, Joel! Keep doing what you do! You’re doing a fantastic job.

        • You are going to encounter Resistance every step of the way. The ability to forge ahead without unnecessarily alienating those you care about is a fine balance.

          You have a good situation, being able to bootstrap. Make allowances, if you feel it best, to be able to enjoy the financial support you’ve got now. But know that even when you’re successful, some folks will never understand why you don’t “get a job” and they’re often the ones closest to you. (My mom still sometimes refers to the time my family “lived in our van” when in fact, we spent 2 years as nomads, house-sitting gorgeous homes in beautiful locations all over the US and Canada; I can’t help thinking she envisions us on a street corner with 3 sizes of tin cup for Daddy, Mommy, and Little One.)

          How can I help you with whatever’s your biggest challenge right now?

          • It really is a fine balance! At times, it’s frustrating trying to achieve that balance and constantly having to explain myself. I definitely need to improve on that.

            And that sounds like a really fun lifestyle – I’d never equate it to living on a street corner! lol Being somewhere new all the time seems like such an adventure!

            Right now, though, my biggest challenge is finding new clients for my freelancing business whilst standing out in a very competitive market. My main pursuit, however, is music, but I’m not too worried about that. I’m looking to collaborate with other like-minded musicians – but in the meantime, I have bills to pay. So finding more clients that I can help out – which, in turn, would help ME out – is my primary focus. And getting started in the music industry isn’t necessarily cheap, either. Sadly, we can’t all have Justin Bieber’s luck lol

            • If you wanna talk about doing business with art, there’s this guy named Mark McGuinness . . .

              What makes what you do unique? Who is going to choose you instead of anyone else in the world? And why?

              We all know about “unique selling propositions” but what that means in a service business is infusing your personality, ethic, and style into the work, so people are choosing you, not what you do. As Simon Sinek says, people don’t buy what you do, they buy WHY you do it.