Back in the day, choosing a career was pretty simple.
You didn’t.
You did what your family did, or worked at the only job in the village, and that was that. People rarely switched careers, because there weren’t ‘careers’ to go to.
And as for ‘career satisfaction’…
Well, you did what you needed to feed your family, end of story.
(Our ancestors stuck with careers for so long, they even got surnames attached to them: The Smiths, the Fishers, the Masons etc.)
It sounds horrible, but the irony is…
They were probably more ‘satisfied’ with their jobs than we are!
Fast forward to the present, and take a look at the sheer number of jobs we can do nowadays:
You can be a teacher, a content creator, an influencer, a business owner, a self-taught programmer specializing in one of 20 programming languages…
Plus, the dizzying number of education options - from coding bootcamps, to career change schools, to part time MBAs and ‘externships’…
The result of all this choice?
We constantly second-guess ourselves, we can’t relax & commit to one career, and we’re left with a gnawing sense of FOMO: Did I make the right choice?
It’s a common theme I see in the questions I get in my inbox too, like this one from a few days ago (kinda paraphrased):
“I’m stuck — I could stay at my current company and get promoted in 2 years. But I’m feeling a little bored. Maybe I should join a startup for something more exciting? Or switch careers entirely and learn programming? Or just move to another stable corporate role for a change of scenery?”
Ultimately:
More choices => more uncertainty.
It’s a real problem, so today I thought I’d offer up a few different perspectives that might help.
Let’s go.
📈 Progress >> inaction
When faced with a decision, we tend to freeze up, and agonize over picking the right fork in the road.
A better solution?
Start taking action down one path. Usually you can change your mind later anyway - choices aren’t always as permanent as we think they are.
After all, what’s better: trying to figure out the best option for 6 months from the sidelines, or taking 3 months to try out each one? (The latter!)
Here’s a practical takeaway:
Instead of debating in your head for weeks, spend the next two weeks taking one small step down a path you’re curious about. For instance, if you’re unsure whether to focus on project management or data analytics next year, carve out two afternoons to try a short online tutorial in analytics. See how it feels.
Movement beats endless overthinking.
🖐️ The "5/5/5" rule
Smoked salmon vs. cream cheese? Java or Python? Should I marry Jane or Rachel? When faced with decisions big and small, I like the 5/5/5 rule:
Will this matter in 5 days? 5 months? Or 5 years?
This might help you understand the real weight of the decision and make it easier to choose. Often, many decisions we’re ‘stuck’ on won’t even matter in a few months, much less a few days. Recognizing that takes the pressure off.
🥲 Counteract FOMO with JOMO
Instead of the Fear Of Missing Out, embrace the Joy Of Missing Out:
The liberating feeling that by choosing one path, you're freeing yourself from the negatives of the other paths.
Put a tad more… visually: the grass isn’t always greener on the other side – sometimes it’s dry, unkempt, and covered in dog poop.
An example:
If you choose a stable path inside your company (maybe focusing on building a reputation in your current department), you’re avoiding the uncertainty and stress that might come from hopping to a totally different role somewhere else.
🎲 Lower the stakes
Where we often get in trouble is making huge, rash, life-altering decisions without having the full picture.
IMO, a better approach is designing small, low-stakes experiments to test the waters. This way, you can gather information to make a more informed choice without needing to fully commit.
Let’s say you're trying to choose a career.
Arranging a conversation with someone who’s been in the industry for a while will help you figure out if you like it on an average Tuesday far more than watching a trendy Netflix series or a Youtube ad.
Another example:
You’re thinking about switching careers to become a UX designer: you want to design web and mobile user interfaces for companies. But you’re not sure you’re going to love it.
A low-stakes experiment you could run is to do a freelance design project. Sign up as a freelancer on platforms like Fiverr or Upwork, and do a small 10-hour project at a low entry-level rate. You'll deal with real clients, real deadlines, real problems and get a much clearer picture than you would otherwise.
🧊 You don’t make the right decision…
When I was agonizing over making a decision between two good options, a buddy told me:
“You don’t make the right decision, you make the decision right.”
It sounds weird, but it’s freeing. If there’s no “perfect decision”, then you’re free to pick either and make the best you can of it.
