Why Quitting Your 9 to 5 Is So Hard—And How To Succeed Anyway

I talk to a lot of people who are thinking about quitting their 9 to 5 or are in the process of doing so. But they struggle. This is not so much for technical reasons as for mindset. Let's look at how to fix that.

I.

The first mindset block is what I call the temporary decline in status.

Imagine you are a software developer currently making $100,000 at your 9 to 5.

Now, you have this idea about starting a travel blog, something you feel really passionate about.

But this means you would go from making good money to making almost no money for at least 2–3 years.

Most people won't do it. It is not even so much the financial loss that holds them back as it is having to live like a student again. It makes them feel like losers, even if it's just for the first few years. In their minds, they compare themselves to their well-paid friends and decide that they can't live with this decline in status.

How do you get over this? By projecting into the future.

Imagine what the price will be if you don't make the switch. For the next 20+ years, every day, you will have to wake up to an alarm. You will have to commute, getting stuck in traffic. You will have to put up with your neurotic boss. You will have to stand the office gossip. But most importantly, you will waste half your time awake each day doing something you don't feel excited about.

Compared to this misery, living like a student for 2–3 years should not even register.

If you're not willing to downgrade your lifestyle for a year to have a lifestyle you want forever, you care too much what other people think.

— Jim Carrey

II.

The second mindset block is about having no boss.

This is a funny one. We all hate being told what to do by some vain superior.

But as soon as we get rid of our boss, we start to understand how much we need them.

This is the reality — most people, without a slave driver, won't get anything done. They will do anything but productive work — surf the web, check social media, hang out with friends, etc., until they run out of money and have to find another job.

How do you overcome this?

If you currently lack self-discipline, it is not the end of the world. Just like a muscle, you can train it. You can progressively extend your pain tolerance when it comes to being productive.

The trick is to start small. If you can only manage 10 minutes of productive work per day, do 10 minutes. But do them every day without fail.

Keep this up for long enough, and you will eventually get to the point where you can do 11 minutes. The one-minute extra will hardly register. Now that is your new daily minimum.

Step by step, you keep building your pain tolerance. And before you know it, you are putting four hours of deep work in every day. And suddenly, the results start rolling in.

Going slow is the shortcut.

III.

The third mindset block is what I call the 2 years of hell.

For the first two years or so as an entrepreneur, your life will be absolute hell. What ends up happening is that you are effectively working two jobs.

Let's stick with our software developer example. You just quit your corporate job and started working on your travel blog. So far, so great. But you still have bills to pay. So, you start freelancing on the side.

Now you have two jobs and no life whatsoever. You work 12-hour days, 7 days a week. Holidays? Vacations? Forget about it.

This is ironic, as you started out on this journey to leave your miserable 9 to 5 behind. But now it just got worse.

How do you not give up? By reminding yourself that this is temporary. In this instance, it is really how they say — "Sometimes things have to get worse before they get better."

And I am not just saying this. I have gone through this transition several times in my life, and eventually, you emerge on the other side. And when you do, it will have been worth it. You will have built something you are proud of, and you will now be making good money from it.

I am in Thailand for the next few months, looking out over the ocean as I write up this newsletter. Trust me — quitting your job is something you will never regret.

Until next week,

Niels