For years, I had a deep-seated fear that everything would disappear. The business would stop working, collapse, go to zero, and I’d be left destitute, sleeping under a bridge.
It was persistent. For stretches, I thought about it when I woke up and before I went to bed. I never told anyone, because I thought, well, that’s just me being weird. Some weakness in my psychology.
Then I started meeting other business owners who would confide the same thing in a quiet moment. A very successful entrepreneur messaged me recently and said, “Deep down, I think I just believe that all of this is going to disappear.”
The Fear of Collapse Is a Stage, Not a Weakness
The fear is a stage, not a weakness. Bottled up, that fear changes how you run a business. Running a business out of fear is not the same as running one out of abundance.
It comes from a predictable point in the business journey. You can work through it by turning abstract fears into concrete proof and closing the gap between where you are and where you’d be genuinely secure. It starts with recognising which kind of entrepreneur you are.
Why Accidental Entrepreneurs Get Stuck in the Middle
There are, broadly, two types of entrepreneur. The born, type-A entrepreneur has a strong internal belief that they’re going to crush it and everything’s going to be okay. If the business collapsed, they trust they could rebuild it.
Then there is the accidental entrepreneur. They landed in it somehow. They were doing something else, started something online, and now find themselves at the helm of a business without necessarily feeling wired for it.
I count myself in the second category, and I think there are far more of us.
The accidental entrepreneur lives with an uncomfortable thought working away in the back of the mind: maybe I just got lucky. If everything did go badly, I’m not sure I could repeat it.
That fear does not strike in the early days, when you’re going from zero to one and have very little to lose. It also does not strike at the far end, once the business is stable and your personal finances are secure enough that a collapse would not leave you in trouble.
It strikes in the middle. You have a business now. It’s your job, but it’s not quite mature enough, and your personal finances are not quite safe enough, for you to relax. You still have to hustle.
In that middle stage, you’ve gone from having nothing to lose to having something to lose. Loss aversion takes over. Losing something feels far more compelling than the fantasy of gaining something.
At the same time, your psychology flips. The question changes from can I make some money? to can I make enough that I could retire and still be okay if the business disappeared? It flips on a dime. Where’s the middle ground there? There isn’t really one. At some point you go from wanting to make some money to feeling like you need to have so much. Once it flips, security becomes a race, and that race creates pressure.
You started the business because you had something special: a strong work ethic, a skill, an X factor. That is what made your business successful in the first place. But you start to convince yourself it was not skill, it was luck. None of that is rational, but it governs your thinking.
The way out is to move these thoughts from abstract to concrete.
Turn the Vague Fear Into a 10k-a-Month Worst-Case List
Much of this kind of business fear is abstract. A thought floats around your head, too slippery to pin down, and the result is anxiety. The first job is to move it into the concrete, because once you quantify something, it becomes much harder to keep worrying about it.
One of my favourite activities was writing what I called a 10k-a-month list. The question was simple: in the worst case, if the whole business disappeared, how could I still make 10k a month to buy food, pay the mortgage and cover taxes? For you, the amount does not have to be 10k. Use whatever monthly figure would cover your basics.
I wrote down every way I could think of. I could call business-owner friends and ask if they had a job for me. I could do freelance email copywriting. I could sell my skills on Upwork. I could offer one-to-one language classes. I could offer business coaching.
There were quite a lot of ways to cobble together 10k a month in the worst case.
Then I printed it, stuck it on the wall, and saw it every day.
It felt like a silly thing to do, but it had an amazing effect. Several times a day, I would see the list and realise: hang on, it doesn’t make sense to have this irrational fear. Even if the business disappeared, I could still do all of these things and make enough to survive. I wasn’t going to be sleeping under a bridge.
That is the point. Once the worst case is quantified, the abstract fear loses its grip. You’re no longer worrying about a vague collapse. You’re looking at specific ways to survive.
But the next thing I did was start some side projects to prove to myself that I wasn’t just a one-hit wonder. I actually do have some entrepreneurial skill there somewhere.
Prove Your Skills Are Repeatable with Side Projects
I started a side project with a friend called Creator Empires. It runs mastermind events and communities for entrepreneurs. It has been going for almost ten years, has generated revenue for that whole time, and is genuinely fun.
I also started doing consulting inside other education companies, helping them work through whatever problems they were facing.
This kind of breaks the rules of entrepreneurship, right? You should really be focusing on one thing, because that’s how you grow something to its full potential. But the reality of running a business is not clean-cut. You’re not just focused on growth at all costs. You also have your own psychology to manage.
If you have a fear that everything will disappear, one of the easiest ways to cut it out is to prove to yourself that you can make money in other ways.
Side projects teach you that you are an entrepreneur, not a one-hit wonder. In my case, Creator Empires and consulting became evidence outside the main business that the skill was not pure luck.
Over time, that adds up. The 10k-a-month list shows you could survive. A side project shows you can build outside the main business. Consulting shows other education companies will pay for your help. Together they become enough proof that the fear starts to look illogical.
In my case, it took quite a few years. Eventually the proof was so overwhelming that my brain gave in and said, okay, I can probably stop worrying about that now. I haven’t had the worry again for years. I think I probably could have got there faster if I’d been a little more intentional about it.
But there is one more piece, the background music to all of this: keep your finances and lifestyle costs in check.
Keep Lifestyle Costs Low So Security Stays Reachable
There is a gap between where you are right now and the financial place you need to be in order to be genuinely secure. High lifestyle costs make that gap larger.
It’s hard to feel financially comfortable when your lifestyle costs are high. If you buy the big house, buy the car, and take on the obligations that come with them, you’ve pushed the feeling of security further down the road.
This is the big danger of lifestyle creep. When you start making money, you feel you’ve earned the right to spend some of it. You absolutely have. But if what matters to you is feeling secure, keeping your costs down is one of the fastest ways to get there.
I think it can be worth avoiding debt where you can, and paying it down aggressively, even if it might not make sense from a taxation perspective. The lower you can keep your lifestyle costs, the sooner feeling secure gets within reach.
When your costs are low and you have proof that your skills are repeatable, security no longer feels so far away.
The Fear Does Pass
So start with the list. Write down every realistic way you could make the amount you personally need each month if the business went to zero. Print it. Put it somewhere you’ll see it several times a day.
Then let the other work accumulate behind it. Keep lifestyle costs low. Pick a small side project that proves you can make money outside the main business.
The fear does pass. I think I probably could have got over it a lot quicker if I’d been a little more intentional about it.
Entrepreneurship is full of these strange psychological quirks. You can easily feel guilty about having them. They can make you feel inadequate, or somehow deficient. But they are real.
