How to (finally) quit your job to start a business

Person jumping between rocks.
Take the leap. Source: Unsplash

My first post, in which I announced that I quit my job as a software engineer, has stirred up a reaction beyond my expectations. I’ve heard the following from different people:

  • I’ve been thinking about doing this for years
  • I wish I had the guts to do this
  • You’re so brave
  • I’m excited for you

I’m not gloating — I just think these illustrate well the fact that I somehow struck a chord with a lot of people. I suspect that there’s plenty of you who are thinking of quitting their jobs and changing their careers or even venturing out on your own into self-employment or entrepreneurship.

If you’re one of these people, this article is for you. I’ll describe the ways of thinking that helped me finally pull the trigger and offer some advice based on my experience.

Why quit your job?

If you’re thinking of quitting, you probably already know the reason. It’s possible that it seems nebulous because you’ve never articulated it clearly, or even that you refuse to admit it to yourself.

But it’s also possible that you have no idea what to do with your life because you’ve always followed the plan that other people had laid out for you.

Some good reasons to quit are:

  • you dread going to work
  • you stopped growing and learning
  • you’re stuck in the comfort zone and need new challenges
  • you would rather do something else with your life
  • you’re not making enough money
  • you don’t want to work on a schedule and ask for permission to take holidays

However, just because you’re dissatisfied with your job does not mean that you should quit and start a business. Self-employment and entrepreneurship are hard, a great source of uncertainty and anxiety, and can be an emotional roller-coaster. Rather than starting out on your own, you could simply redefine the role with your existing employer or find a different job. But if you don’t want to do that, read on.

The standard life plan

Most people in the modern, developed world, follow this standard recipe:

  1. Go to school and college/university, get good grades
  2. Get a respectable, well-paying job and do it for 40 years
  3. Retire in your 60s and finally enjoy the freedom that you earned

But is it really the best plan? And do you need to follow it?

Think about it, in your 20s and 30s you’re in your best physical form. Probably without huge commitments like kids, a mortgage, and social obligations. Do you really want to spend the best time of your life working 9-5 and only having two days per week plus a few weeks of holiday per year for yourself?

The promise of freedom in retirement is not an attractive one for me. If I’m even still alive in my 60s, I’ll be frail and sick. After a lifetime of working in a career and having my identity built around it, I’ll suddenly have to reinvent myself. Find a new way to keep busy.

That is no easy task, particularly if you’ve spent your entire life denying yourself the opportunities to follow your heart’s desires.

The sense of purpose and meaning is what keeps you going in life. If you don’t have it in your old age, you’ll give up enthusiasm for life and die well before you should.

Do you want to be an old man or woman, regretting the things you’ve never done, in anguish because it’s now too late?

You won’t be young forever. Seize the opportunity now.

Why are you at this job?

Does getting out of bed fill you with excitement or do you dread showing up to work every morning?

Ask yourself why you took your job in the first place and why you’re still in it.

Often we choose careers without knowing what the day-to-day would be like. The reality of the job is usually very different from our expectations.

Maybe the job seemed like a natural progression of your schooling. After studying computer science, the normal thing to do is to become a software engineer. Maybe this profession has been your dream since you were a kid. Maybe you chose a career based on an interest. But the reality of the job is really not that exciting. Then it’s time to think about a change.

Or maybe you’re trying to please someone else. Maybe your parents really want a doctor for a son, or you come from an engineering or business executive family. Or you simply subconsciously feel like you should follow in your parent’s footsteps. In this case, you need to decide what’s more important to you: your family’s approval or the agency over your own life.

You could feel pressure from friends and society. Maybe you believe that the best way to achieve social status and respect of others is to have a reputable, high-paying job in an esteemed institution. But I guarantee that seeking the approval of others is not going to make you happy. In fact, it will have the opposite effect.

Or you may feel that after many years of education and training in a particular discipline it would be a huge waste to throw it out the window. After years of studying medicine, how could you not become a doctor? But that’s a false problem, because you can still use your knowledge, skills and experience to do something else.

Your experience gives you an unfair advantage that you can leverage in business. For example, an entrepreneur with a background in software engineering or medicine absolutely should use their experience in business. They can use their knowledge in ways to make themselves unique — for example by noticing a problem that people in their profession have or solving a hard technical problem using their skills.

You shouldn’t be too rigid with your identity. If being a software engineer makes you miserable, then stop being one. Use the skills you gained in some other way.


The big one for me was fear of uncertainty. I knew that I wasn’t happy in my job and was thinking of quitting. But I delayed doing it until I knew what I would do afterwards. I went as far as writing down detailed requirements for my next job and was prepared to spend months looking for the perfect gig. But because of my natural tendency to make plans and minimize uncertainty, I was delaying quitting my job until I had a really good plan and idea of what to do next. But finally, at one point I had to admit that I couldn’t delay it any longer. The job was not working out for me and I needed a change. I had to embrace uncertainty, make the jump, and figure out what comes next later.

But there are other things you may fear. Your parents’ disapproval. Your friends thinking you’re crazy. Losing all your money. Public humiliation from failing.

The thing is, you shouldn’t let fear make decisions for you. More often than not, it stands in the way of making the right choice.

Fortunately, there are ways of working through fear. Here’s an exercise I found in Tim Ferriss’s life-changing The 4-Hour Work Week. When you’re avoiding doing something because of fear, ask yourself these questions:

  1. Define exactly what you’re afraid of. What is the absolute worst-case scenario?
  2. How bad is it on the scale from 1 to 10, where 1 is a minor inconvenience and 10 is permanently life-changing?
  3. How likely is it that the worst-case scenario actually happens?
  4. If the worst-case scenario happens, what could you do to get back on your feet?
  5. What can you do to mitigate the risk of the worst-case scenario happening? To make it less likely to happen?
  6. If you do what you’re afraid of, what are more likely outcomes? What good consequences would they have?
  7. What is the cost of inaction? What will you miss out on if you delay acting by a month, a year, five years?

Let’s go through an example and analyze the financial impact of me quitting my job.

  1. The worst-case scenario is that my experiment of self-employment and entrepreneurship fails. I run out of savings.
  2. In the grand scheme of things, this would not be very bad, maybe a 5 out of 10.
  3. And honestly, I think it’s not very likely. My partner makes enough money from her job to cover our living expenses, and even without it we have enough savings to survive 2 years (though this ignores any investments I may want to make in my businesses).
  4. If I really run out of money, I’ll start freelancing, contracting, or find another full-time job.
  5. I can minimize the risk of running out of money by not spending frivolously and bootstrapping projects with minimal expenses.
  6. It’s likely that I find some way of making money that doesn’t involve working for somebody else. The consequences are that I could cover my living expenses with much more satisfaction in my work and potentially make much more money than in full-time employment.
  7. The cost of staying in my old job would be a constant feeling of dread, burnout, and low energy. In a few years, it could turn into depression and massive regret.

Have a plan

It’s good to have a plan with respect to your finances and what you will do after you quit. Think about your plan, but don’t overthink. Wanting to have a perfect plan can be an excellent excuse to not do anything. But some planning will be important.

Take stock of your finances. How long could you survive on your savings?

If it’s only a few months, you should really read up on personal finance. But even then, you have options. For example, you could work a part-time job or do freelance gigs. This would make just enough money to pay for your living expenses and leave you time to work on your own projects. That’s just one option — the point is, when you define a problem well and think creatively, you’d be surprised how often you can find a solution. But you need to keep an open mind and be willing to try unorthodox things.

And in fact, you don’t even need to quit your job before starting your business. A lot of people build side-projects while they are employed and only quit their jobs when the project gets enough traction. This is a much safer option if you can find the time and energy to do it in addition to your main job.

Closing thoughts

If you’d like to explore the subjects in this article in more detail, here are some books that profoundly influenced my thinking. I highly recommend that you give them a go:

  1. The 4-Hour Work Week – Tim Ferriss
  2. Designing Your Life – Bill Burnett & Dave Evans
  3. Show Your Work! – Austin Cleon

If you’re unsure what you want out of life, start by just asking the question. Keep thinking about it and the answers will eventually come. Some tools that you can use to help this process are journaling, meditation, retreats, coaching and psychotherapy.  

Let me know in the comments below if you found any of the ideas in this article useful. If so, also consider sharing them on social media and signing up with your email to keep updated on new posts.

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