I feel like what most people consider "risk" is more "fear of unfamiliar outcomes". To a gambler, a "risky" bet in a card game doesn't feel like it because both outcomes, winning and losing, are familiar. However that same gambler might not want to risk a smaller amount of money, even if the odds were better, in an unfamiliar situation.

So my advice is find safe ways to become familiar with the outcomes. Put yourself in situations where you will fail, or most likely will, but the stakes are low enough that it doesn't matter.

If you're worried about risking your time and energy on a side project, do a weekend version of it first. Find contests, hackathons, challenges that provide a scaled down, structured version of whatever you want to do and do those. Immerse yourself in the space (don't pretend to be an expert, just learn all you can), help people on related projects, and soon enough it won't feel risky anymore, you'll have a realistic intuition of the outcomes.

Also, beware of letting FOMO and envy motivate you. Those evaporate quickly.

It's like any muscle. Start with something small that feels very risky, but isn't. Maybe 5hr-per-week unpaid tech work for a charity you enjoy, or a 10hr-per-week paid gig. Buy and sell some stuff online for small money. Do things where, even if you failed COMPLETELY, it wouldn't really affect your life.

Eventually you'll find that your universe of "acceptable risk" has expanded. Previously risky things won't feel that way anymore.

Extreme risk tolerance is a skill, but it comes from a lifetime of trying things, having them fail, and finding out that actually it was okay.

Realize that the risk of failure does not equal the risk of catastrophe. If your side project fails, in all likelihood you will still have your health, wealth, and sanity. "Catastrophizing" is a psychological term for the irrational belief that any wrong move will be the end of you. Be rational: A side project is not guaranteed to succeed, but if it fails all that happens is you have gained valuable experience and are better equipped for your next venture.

It sounds like you're more averse to calculating risk. If you have your risk calculations right, there's no FOMO.

Have a baseline for your default path. In this case, it's corporate ladder and promotion. How much are you investing? Maybe an extra 20 hrs/week for a 50% chance of gaining $3000/year in income? That nets to about $1500/year, $1.44/hour.

What about a side project? Maybe 30 hrs/week, 10% chance of making $500/month. So about $0.38/hour.

So in that situation, the side project may not be worth it and there would be no FOMO. But if the numbers change - less odds of a promotion, or higher income from a side project, the calculations change. This is also missing the 1% chance of making $5000/month and you might want to add that.

If your problem is that you don't trust statistics enough, maybe try playing more games. Something like poker will give you a better intuition for it, whereas a game like Xenonauts might build an intuition for being cautious but taking risk where necessary.

I used to be super risk averse. One thing that helped me is to play games that punish being too risk averse. For me, that game was Poker. In Poker if you are too risk averse, since the game is naturally adversarial, you get crushed.

I would play online on PokerStars with free fake chips and over time I could actively feel myself becoming more risk seeking. I no longer always thought my opponent was better than me. I would bluff in crazy positions just to see what happens. Occasionally I would overstep my boundaries and become too risk seeking. Overall the game forces you to become more rational with how you perceive and act on risk. Would highly recommend!

A side project IS very risky if you expect it to make money directly.

If you want it to advertise your skills however, in my experience it works well.

Rather than climb a corporate ladder, you can try yourself at some interviews and see if you get a better deal elsewhere.

Typically, larger companies won't offer a raise by themselves, and you have to show them a counteroffer for them to listen.

But you can also take the counteroffer if they don't update your pay.

From my personal experience, sport help you develop the lack of fear for taking risks. Especially contact sport, as your body is in physical risk.

But, now, with almost 40 years of age, life got me ups and downs. So, now, I would say, make an assessment of the risk. What is the worst case scenario? If there is no logical reason, then just do it.

For example, what is the risk of living? Well, you can end up dead, but eventually, everybody dies, as life ends with death.

So, what is the risk for leaving a steady good income job and work on your project or a startup? Well, the risk is that you will lose steady income, maybe you will not have money for rent, food etc.. on the other hand, if you succeed, you will never need to think about money again.

If you fail, well, the risk is that you will need to find a job, start from bottom, but hey, you were there, on the bottom, and you know your way up. So the risk is minimum.

When you do want to focus time on a side project what's been most effective for me is to mitigate that risk by using stable income from a corporate job to establish savings. Then use that savings to take some time off to focus on a side project.

It is hard. And I don't know how to do it. I also have strugle with this. I was raised near the iron curtain so I understand this context. When I was leaving the job at state institution to go to freelancing a lot of people were like "Are you crazy? Leaving the job that you will have for rest of your life?"

Every job change was a challenge and stressful. You never know where will it lead. Did you miss out on something by leaving the job?

You know what works best for me? I try to leave by "There are no wrong choices. There is only life after the choice".

Only stake what you can afford to lose. Unfortunately this is somewhat dependent on your socioeconomic background.

Don’t YOLO your life savings on a business unless you have a fallback. Take Microsoft: if that company had flopped, Bill Gates had a prestigious and lucrative academic career to fall back on.

Not having the anxiety of failure==material insecurity will free up cycles to develop your endeavour.

There is some great advice here already, so I'll just add: From an ROI perspective, climbing the corporate ladder is actually very risky. You must invest a ton of time (years) and energy. Do things you may not want to do. Yet only a very few reach the top. Trying other things, like a side project, will yield success or failure a lot faster.

strategies I've used, with emphasis on derisking primary fear:

* decompose risk into small incremental steps, e.g., code the smallest dumbest thing possible in some new language, write a post about a problem instead of launching right into startup, etc.

* add bigger fear that forces you past other fear -- e.g., added juggling to some public talks for a while after feeling nervous about prep -- even if dropped a ball on-stage, talk was easy

* practice, practice, practice -- e.g., practice pitch every day and iterate it

* plan the next step -- ok, next i will, so response becomes automatic

* make it harder -- building a rocket to moon -- nah, building a rocket to fix James Webb if it breaks -- usually opens up fresh ideas

* sleep & other self-care

* breathe

You need to experience failure to realize it’s not as bad as you’re making it out to be.

To overcome the fear of taking rsisks... you need to take a risk.

Sounds banal (it is) but this is the only way to make it happen.

Though you always can try things with low cost and high reward first, like parachute jumping.

Here is how I think of it. No one is as concerned with my employment as I am. I cannot control what happens in a company owned by someone else. The economy is much more dynamic than it used to be. In the USA, at least, there is no loyalty either way: from the company to the employee or vice versa.

Therefore paradoxically it is safer for me to work for myself than for someone else.

And in the case of us tech types, we have an advantage in that we can often conjure up a business out of nothing. Maybe it’s just search engine optimization, maybe it’s a website agency, maybe it’s an application that you sell. So if you are a programmer, the cost of building your business can be minimal. If you pursue some more expensive form of tech startup, you can easily get funding for it if you’re good or the idea is good. (in the USA, venture capitalists tend to invest in the person more than the idea.)

I took this approach starting in the 1970s and have been mostly self-employed since then. It has worked out very well financially. I consciously decided to put family and work life balance first, which I knew would limit my earnings. I made millions, not hundreds of millions, but that was plenty. My strategy was to take plenty of risks that I could afford, and go for consistent singles or doubles instead of depending on home runs.

There's not necessarily anything wrong with living a low risk life.

The Man In The Mirror

When you get all you want and you struggle for pelf, and the world makes you king for a day, then go to the mirror and look at yourself and see what that man has to say.

For it isn’t your mother, your father or wife whose judgment upon you must pass, but the man, whose verdict counts most in your life is the one staring back from the glass. He’s the fellow to please, never mind all the rest.

For he’s with you right to the end, and you’ve passed your most difficult test if the man in the glass is your friend. You may be like Jack Horner and “chisel” a plum, And think you’re a wonderful guy, But the man in the glass says you’re only a bum If you can’t look him straight in the eye. You can fool the whole world, down the highway of years, and take pats on the back as you pass. But your final reward will be heartache and tears if you’ve cheated the man in the glass.

– Dale Wimbrow, 1934

This is wonderful. Thanks!