When did starting up a business become the only acceptable reason to leave your job?

It seems like everybody is starting up a business these days. It’s the done thing. All the cool kids are doing it.

Indeed a recent survey by LearnVest in the US found that the two most aspirational careers right now are CEO (36%) and entrepreneur (28%), with lawyer and banker registering a mere 2% each. Hardly surprising.

It also seems that starting a business is the only acceptable reason to leave your job. I certainly felt that I could hide myself in a cloak of invincibility when I left my job at a big law firm and said I was leaving to start up a business. I didn’t say “I’m leaving to write a novel” or “I’m going to start a blog”, which are two things I actually have done since leaving. It’s not that I was lying to my former employers; I genuinely believed I would go start a business — I still do.

Of course this isn’t a new phenomenon. People have always started up businesses, we just didn’t call them “startups”. And there is a non-trivial difference between the types of businesses people are starting today versus what they left traditional career paths to pursue a decade ago.

People used to leave good, solid corporate jobs to open a restaurant, cafe or shop in their local neighbourhood. Or maybe they took over a derelict pub. Or maybe they went into property. They indulged in a dream of a quiet existence. They wanted to be their own boss.

Now they leave to build apps or websites or platforms or gadgets. They dream of anything but the simple life. They dream of striking gold.

What’s the key difference between these different classes of ventures? In essence it boils down to one thing: risk. Clearly opening a restaurant is risky, and many, many new restaurants fail every year, this has always been the way. But the risks are known risks; they are quantifiable. It’s a question of location and footfall, of serving enough customers in a sitting, of containing the costs of rent and produce and staff. A bank manager can look at your business plan and begin to assess your likelihood of success because she has seen many restaurants open and close in the area; she knows the good business models.


A bank manager cannot even begin to tell you whether your app is going to be the Next Big Thing. No one can. Even you don’t really know what your product is, or who your customer is, until maybe a year into the process. You can guess at it while you’re daydreaming on the tube about your seaside condo in LA, but you don’t know for sure until you’ve built your product and taken it out to the market.

People often don’t take the necessary time to ponder this distinction. It’s not just that you have to be entrepreneurial, savvy, smart, driven, hard-working and ambitious, although you undoubtedly have to be all those things. You also have to be something that’s completely out of you’re control. And that is: really, really lucky.

So why do people do it? It’s the same reason why thousands of young, hopeful Americans pay tens of thousands of dollars to put themselves through law school even though only a tiny percentage will ever land those six-figure jobs. It’s why people play the lottery.

If you’re a romantic, you might say that these people dare to dream. If you’re a realist you might say people tend to think they are luckier than they are. If you’re a cynic you might say people are stupid.

An interesting theme that has emerged when I ask other escapee lawyers why they chose the startup route, with unknown risks and an unknown trajectory, is that they are willing to take a punt that they may hit the jackpot. Perhaps this is unsurprising – these same people also backed themselves in the race to the top of the legal profession.

Also since it tends to be a digital product that they are developing, it can be worked on from anywhere and at any time, which suits prospective job-leavers because they can tinker away before and after work and at weekends.

This feeds into the main rule for leaving your job, which I unequivocally broke: don’t leave without something lined up. It’s ironic that the people who go out and start businesses can be somewhat risk averse in this way, but lots of people tell me they wouldn’t dream of leaving a job without something set up beforehand. Personally, I didn’t have the mental or emotional energy to make those kinds of decisions while I was still working.

But even more interesting, when I probe further as to why startups specifically, some people end up saying that although they recognise that they may end up giving 3 or 4 years to this venture, of working harder than they have ever worked in their lives, they also see that the rewards might be so big that they would then be in a position to do whatever they wanted with the rest of their lives afterwards. Then they could live the life of Riley.

Hang on a minute — doesn’t this start to sound a lot like the exact reason for leaving the corporate job in the first place? It was for me. I was tired of deferring my happiness and my life to some later period when I would be rich and able to do whatever I wanted. I was desperate for something that gave me more time to live my life, not less. I wanted freedom from being told what to do, not new masters in the form of investors and stakeholders.

I have no problem with unknown risks — I have taken plenty of risks in my career — but this aspect of the startup route set my alarm bells ringing. It sounds no more compatible with being healthy, having a family, getting enough sleep and reducing stress than working my way up the law firm ladder.

Now some of the preconceptions about how a startup is run are based on movies like The Social Network which show young entrepreneurs, walking around in hoodies, staying up all night to code. If you’re your own boss you don’t have to run your business like that if you don’t want to. You don’t have to engage in the macho game of who drank more Red Bull and who sees their family less. It doesn’t have to be all-consuming unless you want it to be.

And there are lots of good reasons to join or create a startup, and all of the investment, in terms of time, energy and, yes, money, will be worth it because you will have created something you are passionate about, something you are proud of, something you love. If you find the right business for you. If.

People talk about product/market fit, but rarely about product/entrepreneur fit. Very little of the advice coming out of Silicon Valley and Tech City even mentions this aspect of choosing a business idea.

The only people who seem to be talking about this “if” at all are the wonderful guys and gals over at The Happy Startup School. They recognise that the first step in creating a happy, healthy business that puts out a quality product that customers love is to design the life you want and come to a business model that fits in with that life. They ask aspiring entrepreneurs questions like “how happy are you right now?” and “what would it take to make you happy?” and “what does success look like to you?”. These questions force you to take stock of what you are hoping to achieve from quitting your job and starting a business.

This is something I’ve been thinking about a lot because I have so many business ideas buzzing round my head and it’s so tempting to just jump at the first one and throw myself at it.

So one of my serious ideas, for example, was a platform for lawyers to share know-how with their teams. This would be expensive and time-consuming to set up and to run. It would probably require outside investment. I’d have to negotiate with the bureaucratic procurement divisions of law firms. It would be a long time to get the product to market. Yes, it could make millions. But I decided it’s not worth it, for me. I’ll let LexisNexis or PLC take that one. You’re welcome, guys.

After this realisation I was left seeking an alternative. I got on with writing my novel, I kept writing my blog, and I continued to sift through my folder of “Big Ideas”.

Then I had a breakthrough.

I don’t have to keep looking for a Big Idea, because maybe I’m already living it. Maybe this is what I want to do; maybe this is the Big Idea, or at least the beginning of it. I don’t want to start a big business that will take over my life, I want to run lots of small projects that take advantage of my unique set of skills and interests.  I want to change the world, but I don’t want to sacrifice myself to do it.

Hardcore entrepreneurs may sneer at my lack of vision and ambition, but I think I have bags of both. I want to create amazing content and products that people love to engage with, while also creating the type of life I want to lead. When I say “small project” I mean that it won’t take over my life, I don’t mean small in terms of impact. And I want to make money doing these things. I think that’s massively ambitious!

Maybe this is what people mean by being a “portfolio worker” but that doesn’t sound right because because it fails to capture the truly entrepreneurial flavour of the projects I have in mind.

Similarly “freelancer” also doesn’t cut it — you can’t be a generic freelancer, but “freelance entrepreneur” doesn’t really mean anything. For now at least, I don’t want to work for other people.

Maybe it’s a “lifestyle business”, but that makes it sound like a hobby or something you are doing just because it fits with your lifestyle and not because you really care about it. The term also seems typically to be used when describing people who are blogging for a living to fund their worldly travels. That’s not what I’m envisioning. I’m not talking about making money from my blog, I’m talking about multiple projects, some that pay and some that don’t.  Maybe I’ll do them concurrently, maybe not.

I think it’s time for a new word, a new phrase, a new way of thinking about people who reject the traditional career path but also reject the idea that the only alternative is a single type of venture. It has to leave room for different solutions for different types of people who have different goals and dreams. We need something that encompasses the themes highlighted by The Happy Startup School, including passion and designing a life you want to live. I think it’s time we start to recognise the workerbees who are opting to be truly free.

Career pioneer image

I’m going to call these people Career Pioneers. People who forsake the traditional, linear career path in favour of exploring and pursuing different endeavours. People who push the boundaries of how to earn a living in this modern and connected world. People who leave good, respectable, steady jobs because there has to be another way. People who forge their own life from the different aspects of their interests and talents. People who pursue businesses, projects and ventures maintaining the freedom to live their lives the way they want.  What do you think?  Is anybody with me?

Have you decided to start a business? I’d love to hear about how you made the decision and the impact that it is having on your life.

Love links, hate distractions. Now that you’re done, here are lots of internet bits to put this article in context:

Check out my post on Seeing Your Career as a Startup for more on applying an entrepreneurial approach to your own life.

If you want to dig into the American Dream report by LearnVest you can access it here. I found it via The Muse: Why Lawyers and Bankers are Leaving their Jobs (and Where they are Going).

If you want to learn about the difference between a small business and a startup, who better to hear it from that the godfather of the lean startup methodology, Steve Blank. Interestingly he specifically addresses the dismissive attitude that tech entrepreneurs have for people who run small businesses and calls it out as bullshit. I would only disagree with him that you don’t have to give up your life to take over the world, in fact it’s preferable if you don’t. You may not grow as quickly, but you may grow more effectively, efficiently and sustainably.

Check out this old NYT article about how the American law school system preys on the hopes and dreams of naive students, which I read while studying at Georgetown Law for my Masters (!).

This post by Rob Symington, co-founder of Escape the City, is essential reading for anyone trying to weigh up the practicality of different business ideas. It asks you the important question of whether you are the right person to bring your idea to market.

This is another great summary about picking a business idea, written by Adam Fletcher and Paul Hawkins of The Hipstery (a store based in Berlin selling quirky and humourous German designy goods. What else?!). It looks like these guys did pick a business that fits with their life, but alas they did not mention this in the post!

Penelope Trunk recognises that there are different types of entrepreneurship in this awesome post: Entrepreneurship is a spectrum: find out where you are. See also How to know if you’re an entrepreneur, which is about doing something on the side of your main job, and for a cute story about her little boy’s egg-selling business.

A great post from Tess Vigeland, a public radio broadcaster, on making the leap without a safety net and leaving a job even if you loved it once (thanks to @EmilyFord1 for sending this to me!).

Another article, this time by Sam Baker, a former magazine editor, on leaving your job with “nowhere to go”.

Charlie Hoehn is one of the few people who writes about why anyone would want to leave a successful tech startup. He did just that and has since written a book about dealing with anxiety, which may be less sexy but is probably far more valuable to the world.

Marianne Cantwell embraces the idea of creating a “free range” career that suits your lifestyle every day. She runs workshops and has a book called Be a Free Range Human: Escape the 9 to 5, Create a Life You Love, and Still Pay the Bills. Thanks to @Char_Davies_ (another recovering lawyer!) for sending this over.



8 thoughts on “When did starting up a business become the only acceptable reason to leave your job?

  1. YES! This: ” I wanted freedom from being told what to do, not new masters in the form of investors and stakeholders.” is exactly what I’m talking about in my book (thanks for linking to it!).

    There are so many forms of business that do not require this and quite a few new-style entrepreneurs (or free rangers as we call them) refuse to take funding. Yes there are some businesses that require it when there is something expensive to build upfront but increasingly people are realising that’s not the smartest approach as a) you don’t get to iterate and evolve as easily when you are answerable to a higher authority b) you don’t have the same impetus to make money and therefore commercial considerations aren’t built in from the start (see the book ReWork for a lot more on this) and c) a lot of what people spend money on upfront in a business? Is a waste of time. You do not know what you REALLY need and what makes that 20% impact (rather than the 80% waste) until you are out there, doing it. (A few examples in my book built very successful – and very ‘them’ businesses – doing exactly that.

    Besides – as you say – it isn’t as fun :) You are 100% right, most of us don’t quit a job to create another ‘job box’ yet that’s the model most people imagine is open to them. We’re here to do things on OUR terms. Non-linear, evolving or even portfolio ‘free range’ careers are getting more popular for a reason! Thanks for sharing :)

  2. Hi Michelle, I loved when you wrote, “I don’t have to keep looking for a Big Idea, because maybe I’m already living it. “We are what we repeatedly do,” said Aristotle. Engaging on a daily basis on what turns on the “dreamer” side of our personality is the way we can develop something really valuable to other people. Each of us has a unique voice to develop and that takes time and dedication. I’m pretty convinced that “passion” is often the effect and not the cause of repeated efforts for prolonged periods of time (the same efforts that can lead to the development of truly valuable skills, also in economic sense). The cause is pure curiosity. Just that. And that curiosity, thank God, varies individual by individual. It’s unique. (Re: passion, there’s a talk by Cal Newport that is very insightful and provides valuable arguments on how “follow your passion” is bad advice https://vimeo.com/85927282).

    I’m very sympathetic with your views of jumping on different simultaneous projects and try to figure out where one can get. As a “big law renegade” myself (quit without something set up beforehand) and now dividing my time between various endeavours, I can vow the value of following my curiosity and of subsiding to it completely. Even if there are days when I’m throwing pillows against my dining room walls ☺ because I’m chased by doubts and fears of inadequacy. In those moments I keep going. I sing. I write and let joy come back into my veins.

    I can only say keep up with the good work you are doing and keep sharing with your “tribe” of followers, which I’m sure will be growing.

    • Yes! I feel I am just getting to this stage of realisation, literally over the last couple of weeks. I love that Cal Newport video, although the thesis that you should find something you are good at and passion will follow kind of breaks down for people who did just that (i.e. law) and engaged in “deep work” and all the rest of it but didn’t necessarily feel that spark. I don’t think is a fundamental flaw in his theory, I see it as even more reason to experiment outside that comfort zone.

      I know I find it so helpful to hear the stories of people like you who are that bit further along in the process, and I’m sure my growing tribe (!) finds your comments extremely useful too! Thank you.

  3. Pingback: Friday Fess-up: 4th April | workerbeefree

  4. Loved your post. I let a pretty decent “job” that I once loved pull me down into a sea of darkness. I am just now starting to see a bit of light. I wish that I had seen your blog a few years ago. I had always thought I was the “only” person that wanted to work for myself but not in the traditional sense. I am just now coming to terms with myself and the fact that I can be a Career Pioneer and work many different projects at once. I look forward to seeing many more of your posts.

    • Thanks so much! And congratulations on beginning your journey! From my experience so far, choosing and creating your own path isn’t easy – but then neither is doing a job that’s no longer right for you!

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s