I used to be the world's worst overthinker. Every decision, big or small, would send me into an endless loop of "what ifs." In today's Mentor's Corner, I'm sharing what finally helped me break free - and how you can too. If you’ve been stuck on a decision lately, this should give you some clarity.

Before we begin... from our research team.

This is Coached Weekly, my career notes where I share the tiny % of ideas that actually work in real careers. It takes 5 minutes to read, but could speed up your career by years. I write this myself and I read your replies. —Rohan Mahtani (LinkedIn).

It’s okay to have ‘materialistic’ goals

Quick rant: I don't think it's bad at all to have materialistic goals (like wanting to fly business class, or buy a nice handbag). People sometimes get judgy about it, but I think whatever motivates you is good - especially if it gets you moving. Often the "shallow" goals push you and then later on you end up finding deeper reasons to keep pushing forward anyway. So don't discount them - and definitely don't judge others for theirs either.

How I beat overthinking before overthinking beat me

There's a thought experiment called Buridan's ass: place a donkey exactly between a bucket of water and a pile of hay, equally hungry and thirsty, and it'll die — because it can't choose between them.

No donkey has ever actually died from indecision. But I've met plenty of humans who've come close. I was one of them — overthinking everything to the nth degree, wasting days, weeks, sometimes months on decisions that turned out not to matter.

What bothered me wasn't any single bad outcome. It was realising how much overthinking had cost me in ways I couldn't see — all the weeks burned agonising over choices that made zero difference, the mental energy spent on loops that went nowhere.

Here's what actually helped me break out of it:

💪 The real cost of getting it right

For a long time I thought overthinking meant I was being thorough. I was being careful. The word I used was "perfectionist," and I wore it like a badge.

But perfectionism isn't free. It just feels free because the cost is invisible. You don't see the two weeks you spent choosing between Option A and Option B — during which you could've tried both.

For example: before I started Resume Worded, I spent months trying to find the perfect startup idea. Does it have demand? Is it venture-scale? Is the market too crowded? I must've talked myself into and out of a dozen ideas without trying any of them. In the time I spent planning the perfect business, I could've tested five real ones. (Irony is, Resume Worded started as a random side project that broke most of my own rules.)

Once I started actually noticing this pattern — how long am I spending on this decision, and does the outcome even change? — the answer was almost always no. I'd land on the same choice I would've made on day one. I'd just tortured myself for a fortnight first.

That realisation made me receptive to a simple idea I'd have previously dismissed:

⏰ Give yourself less time

There's a principle called Parkinson's Law: work expands to fill the time you give it. Give yourself three weeks to decide something, it takes three weeks. Give yourself three days, it takes three days. And — this is the uncomfortable part — the decision is usually no worse.

So I started setting deadlines for decisions, not just tasks. Can't choose between two roles? Decide by Friday. Tweaking your resume for the eighth time? Ship it tomorrow. (Or finish it once and for all with this tool!)

It felt reckless at first. But the thing about deadlines is they don't just speed you up — they reveal what actually matters. When you only have two days, you stop deliberating over things that don't make a difference. The constraint does the thinking for you.

⏰ Match effort to stakes

Not all decisions deserve the same amount of your time. That sounds obvious, but most people get it wrong constantly.

I use a quick filter: will this matter in 5 minutes, 5 months, or 5 years?

If the answer’s 5 minutes, a coin-toss might do. If the answer’s 5 years, even a week-long hike to clear your head is not a terrible idea.

Sushi or Thai for lunch? Won’t matter in five minutes. Stop treating it like a five-year decision. Just pick.

Conversely, choosing a mortgage rate is a decision that'll follow you for decades — so it probably deserves more than the three minutes most people give it.

The mistakes go both ways. We overthink trivial things because the options are right in front of us, and underthink big things because they're abstract and distant. The 5-5-5 filter helps correct both.

🪧 Kill your options

Here's something I wish I'd understood years ago: the main driver of overthinking isn't that choosing is hard. It's that you're choosing between too many things.

This is why Netflix is so stressful. Not because you can't decide — because you're scanning 10,000 shows, which is a fundamentally different problem than picking between two. The browsing is the problem. Forty minutes of scrolling, and you end up rewatching The Office.

Before you agonise over six options, eliminate four. Cut ruthlessly, then decide between what's left. The act of eliminating is itself progress, and two options is a decision. Six options is a fog.

🤯 An idle mind will eat you alive

This one's less of a tactic and more of a warning: an unoccupied mind is an overthinking machine.

Most of my worst spirals didn't happen when I was busy. They happened when I had little going on — no project, no workout, nothing demanding enough to keep my brain from turning on itself. A free afternoon becomes three hours of replaying a meeting from last Thursday.

The fix is almost stupidly simple. Exercise. A side project. A long walk. Not because these are "self-care" or whatever — but because an occupied mind doesn't have room to loop. You're not distracting yourself from the problem. You're removing the conditions that let overthinking take hold.

꩜ Let your subconscious work

There's a story I love. An intern joins marketer Gary Halbert on a project he has to deliver for a big client. Gary's getting paid $40k but only has a week to do it.

With such little time to deliver the project, the intern is understandably shocked when Gary tells him they should spend the day or two fishing. A few days dater, Gary finally sits down, grabs a notepad, and the ideas just pour out.

The point isn't that fishing is productive. It's that overthinking is often your conscious mind grinding on a problem your subconscious has already solved — or would solve, if you'd get out of the way.

The best thing you can do for a stuck decision is sometimes to do something completely unrelated and let the answer surface on its own.

(I wrote more about this in a recent essay on why you need to embrace boredom in your career — worth a read if this resonates.)

🗺️ Decide, then correct

The deepest source of overthinking, I think, is the belief that decisions are permanent. Pick wrong and you're stuck.

But almost nothing is permanent. You can take a job and leave it. Move to a city and move back. Launch something and change direction.

More importantly: deciding gives you data. You learn what works, what doesn't, what you never expected. Staying in indecision gives you nothing — just more time in the fog.

The trick is to stop seeing decisions as forever-things. They're more like... experiments.

That's what helped me. I hope it helps you make some progress on whatever you've been stuck on.

Hopefully that’s a piece of advice you haven’t heard before. If you enjoyed this:

Speak soon,

Rohan Mahtani
Founder at Coached & Resume Worded

Btw, I like reviews. They motivate me to keep the quality high. Like this one:

You can leave one here. I’d appreciate it. Thank you so much.

🤣 BTW: you shouldn’t be writing your cover letter from scratch anymore. Instead, for a real, actually good cover letter, use this AI cover letter tool. It’ll write cover letters that actually have personality and don’t sound like AI — unlike ChatGPT.

Try it just once for a job you actually want — see how good it is for yourself.

If you’re new here, join at Coached.com to get the next one. If you want the web version, it’s at the top of my list of essays here.