4 Ways to Think About Doing Something “Risky” in Your Career
We have, as a society, labeled some career paths “risky” and others as “stable.”
Doctor, lawyer, banker, consultant, software engineer — stable.
Startup founder, musician, influencer, novelist, freelancer — risky.
It’s true that the “stable” jobs often involve working for a corporation and getting a steady paycheck.
The “risky” jobs tend to be more independent and self-driven. You’re creating something and selling it directly to the end user, or to a major distributor who then gives it to the end user, on a piecemeal basis.
There are so many people that are intrigued by jobs in the so-called “risky” category.
They’d love to be independent. They want creative freedom and to be their own boss. They’re tired of navigating office politics or shaving down their vision to fit corporate priorities.
But leaving their job and doing their own thing seems so insanely risky that they shut down the possibility almost immediately.
Now I’m not saying you should quit your job and launch your own venture tomorrow.
But let me give you a better way to evaluate these so-called risky paths.
Decompose the failure statistic
“Risky” pathways always seem to have massive failure statistics attached to them.
“99% of startups fail.”
“95% of coaches never replace their salaries with coaching revenue.”
“98% of novelists never make a living from their writing.”
Etc. etc. (I don’t know if these are the precise statistics, but you get what I mean.)
These aggregated numbers obscure the true story.
Yes, the vast majority of people who try this fail.
But WHY?
What is CAUSING them to fail?
And do those same causal factors apply to YOU?
If 98% of novelists never make a living from their writing…
But 80% of that failure group is people who only work on their novel for a couple hours a week and spend more time procrastinating than writing…
What are your chances of success if you dedicate your full time, attention, and discipline to getting a novel published?
If 99% of startups fail…
But 60% of that failure group is companies that pivot too slowly and fail to find product-market fit before their money runs out…
What are your chances of success if you stay nimble, pivot fast, and do things cheaply until product-market fit is established?
Don’t be scared away by the aggregate failure number.
Take the time to understand what actually CAUSES success and failure on your risky path.
Then understand which of the success and failure factors apply to YOU.
And THEN decide what the true chances of success are.
Every endeavor has factors that are specific to that space, so dig in and figure out what they are for your thing.
AND let me give you a starting point for some success factors that I suspect are common across many areas:
Discipline and hard work
Giving sufficient time and focus to the endeavor
Some kind of relevant experience that means you’re not starting from zero
Enjoyment of the process
Connections, aka the people you need to sell to (customers, clients, VCs, publishers, whoever) are reachable within a few degrees of your LinkedIn or social network
(NOT that they’re your best friends and you feel 100% plugged in. Just that you can ping someone who can ping someone and get an intro call.)
Financial runway to fail until you figure it out
Whether you’re founding a startup, becoming a fashion influencer, or writing a screenplay…
If you are a hardworking person who knows how to tackle a project with real discipline and commitment
If you can give the project consistent time and focus over a long period of time
If you have some kind of experience or perspective that means you’re not a total beginner
If you enjoy doing the activities that are required to make this endeavor a success for their own sake
If the people you need to reach are a few emails or LinkedIn connections away
And if you’re doing this on the side while you work OR you can tide yourself over with savings for some time while you give this a try
If you fulfill even a FEW of the items on that list, you’ve already raised your chances of success astronomically.
Think in terms of possibility, not probability
Here are the facts:
There are thousands and thousands of coaches that make very little money in their businesses.
A very small number of coaches that make over a million dollars a year in their business.
But what do these facts MEAN?
If you think in terms of probability, this means: There’s a very low chance of creating a multimillion dollar coaching business. I shouldn’t even try. Why waste my time when the chance of success is so low?
If you think in terms of possibility, this means: It’s POSSIBLE to create a multimillion dollar coaching business. These coaches are a proof of concept.
They a concrete demonstration that:
Despite the existence of therapy and Headspace and yoga and thousands of self-help books, there is STILL unmet demand in the market for solutions that help people solve Life Problems.
That the product of “coaching” is an effective solution to those Life Problems.
That people are willing to pay enough for that product to sustain lucrative businesses across many niches.
Don’t use the shining successes in your dream field as proof that you CAN’T do it.
Use them as proof that you CAN do it. You don’t even have to be the first one. They’ve already started charting the path.
Understand your worst case scenario on both sides
Many people evaluate their options solely by looking at the chance of failure.
Doing my own thing: higher chance of failure.
Staying on the stable path: lower chance of failure.
Therefore, stay on the stable path.
Yes, failure seems embarrassing and scary, so people instinctively want to avoid it.
But what actually happens if you fail? And what actually happens if you don’t try?
I asked myself this question before starting my coaching business, and my answers were:
If I failed…
I would go get another corporate job.
My corporate career progression would be delayed by a year or two.
If I didn’t try…
I would lose the optimal financial window to take a risk (I had no kids, no mortgage, and was living at my parents’ house during Covid — there was no better time to take a career risk.)
On my deathbed, I would regret never having tried. (I’ve wanted to be an independent creator for my entire life. Deathbed Pooja would be furious at me if I didn’t even give it a shot.)
Yes, doing something on the “risky” path often involves fear and uncertainty and embarrassment and putting yourself out there in a way that seems terrifying.
And you can absolutely decide you don’t want those emotional experiences, and opt out!
But emotional experiences are different from concrete consequences.
Don’t conflate the two.
Give yourself a chance to look at the concrete consequences of failing and of not trying and then decide which emotional experiences you’re willing to sign up for.
Both paths have their own flavor of discomfort.
Looking at the concrete consequences can help you decide: Which flavor of discomfort is worth it to you?
Get to 50% certainty and then test the hypothesis
You might realize that you have a healthy chance of succeeding…
And that proof of concept of success already exists in the world…
And that your worst case scenario if you try isn’t that bad…
And still not have 100% certainty that you want to do this.
That’s incredibly normal.
There’s so much you don’t know that it would almost be weird if you DID have 100% certainty at this point.
I did this full analysis a couple years ago, checked the box on all three things above, and still only had about 50% certainty I wanted to be a coach.
I wasn’t fired up with conviction and inspiration. It was a coin-flip “maybe 🤷🏻♀️”.
When you reach this point, stop thinking, researching, and theorizing. You’re going to talk yourself in circles and only get more and more confused.
Once you’ve cleared the three hurdles above and you’re feeling a 50-50 sense of certainty that this could be the right path, set a timeline and test the hypothesis through DOING, not THINKING.
Hack together a low-tech version of your product and go get 10 users.
Make a pitch deck and go do 5 meetings with VCs.
Write a short story and submit it to 5 magazines.
Do 5 gigs as a musician.
Do 1 freelance project for free or low cost.
(For me, this was when I signed up for a coach certification and spent six months coaching my peers in the program. I only had 50% certainty I wanted to be a coach. But it was a viable enough hypothesis that I was willing to test it by getting started.)
If you’re thinking of doing something risky or unconventional as your next career step…
I know you want to make the most thoughtful decision possible.
And I’m here to support you however I can.
You can work with me one-on-one over the course of a full coaching package.
You’ll have dedicated time set aside every week to figure out the answers to all the questions above…
Structure and accountability to ensure you make steady progress…
And a space to problem-solve as you gather more data and troubleshoot your path to success.
You can do it on your own — you’re 100% capable.
It’s just way faster and easier when you have structured support.