How To Make That Decision You’re Debating

Here’s what you should do

While I was home over the holidays (visiting everyone and their mom, and my own), three different friends asked my opinion on three different decisions.

  • Friend 1: whether she should sell her 2nd vehicle (a luxury sports car)
  • Friend 2: whether she should move to a different gym
  • Friend 3: whether she should make a career change

Rather than tell them what to do, I asked them these sort of questions. (Though because these were friends and I already knew #1, in all cases, I started with #2.)

1. What are your values?

If you’re not honest enough with yourself to understand what you want in life and how this decision fits into it, you’re gonna have a bad time.

What do you absolutely need, and what sends you into a spiral when it’s threatened? More than one answer is okay. A wrong answer is common. No answer is not okay.

2. What is this “thing’s” primary “job” in your life?

What’s its MAIN goal?

The main job of a job is to earn a living (usually), the main job of a gym is to give us a place to work out. The main job of a sports car is status — and joy.

Many things in life are meant to bring us joy. Not everything — not a job, always, and not a marriage, always, and not our families, always, and not the investments we make into our physical and financial wellbeing, not always — but in a privileged society such as our own, many things are, especially discretionary items such as sports cars.

“What if joy isn’t the biggest factor?”

It may not be — this was an example. Your “decision’s” primary role in life may be something else entirely. That’s for you to decide.

“What if I don’t know if it does the job?”

Then you need to get in touch with yourself. My best tip here? Meditation.

“What if it satisfies some main values but makes me unhappy?”

This is pretty common — especially with things like “jobs” and “marriages.” The primary “goal” of these things often isn’t (much to our misled dialogue around it) to bring joy — joy is an important part of staying with these decisions, but they serve other major human objectives as well (stability, status, security, comfort, consistency, support, fun, company, etc.) Read on.

“What if it does the job but I’m not sure if it’s worth it?”

See next section.

3. What other “objectives” should it serve?

What is its entire “success criteria?”

We go to restaurants primarily to eat, but if you went to a restaurant expecting a.) food and b.) a place to sit, and it only served the former but failed on the latter, you’d (rightfully) call it a bust (unless you knew this going in — or the food was so good you didn’t care; I don’t know. Those are edge cases.)

The point is: what’s the “portfolio” of priorities here? What else is “make or break” after this “thing’s” number one job?

Some things in life — especially the “big” things, like jobs and cities and spouses and kids — aren’t straightforward, and satisfy a web of values.

In the case of a job, it may also be “a sense of purpose,” “status,” “social engagement,” “control,” or even, simply, “something to do.”

For anything, it may be “stability,” “adventure,” “intimacy,” “passion,” “privacy,” “control”… any number of things.

What else does this “thing” need to serve, after its primary job? What are its “requirements,” so to speak?

For a diet, the primary goal is likely weight-loss. But a diet might also need to be affordable, straight-forward, convenient, etc.

With my friend who was debating whether or not to move gyms (when can be costly, not to mention other impacts), I asked her what the pros and cons were for each.

Current gym: she liked the community and the relationships she’d built, as well as the amenities (it’s bigger.) The only con: it’s 30 minutes away.

Potential new gym: it’s 1/2 the distance and the same price. The cons? It’s an unknown community, with no established relationships, and fewer amenities.

So, I asked:

“What’s important here? What do you care about?”

And: “How well might each gym meet those needs?”

4. Is it serving (or will it serve) those goals?

Answering the “primary job” question first.

Friend One asked me: “Do you think I should sell my sports car?”

“I don’t know,” I said. “I can’t make that decision for you. But I will say this: that car’s sole purpose in life is to bring you joy. That’s its only job in life. So: does it bring you joy?”

She sighed. “I mean, it’s just so expensive.”

“Forget about the costs for a second. Pretend there weren’t any. Just ask yourself: does it bring you joy?”

She paused, then said, “no.”

She said, “It honestly doesn’t. It’s finicky and constantly needs work and I hardly even get to really enjoy it, and when I do, I still don’t.”

And the answer, to me, seemed obvious.

If something is not serving its primary purpose, the decision is easy.

That’s not (again) to suggest that everything (especially big things) should be dropped if you’re unhappy — some things, especially relationships and parenting, take a great deal of work. But if something isn’t doing its main job, then fire it from your life.

5. Do you actually care about the cons? Which scenario’s downsides “hurt” more?

Sometimes things just sound bad or look bad on paper, but we don’t actually care deep down inside.

Like motorcyclists who build and rebuild and constantly work on 1970’s café racers. It takes a certain type of rider to own this type of bike, because the ratio of time spent riding to working is like 1:10. And yet they don’t sell them, because for them? The downsides aren’t bad enough to sell them.

Same for parents who have more children after the first one vomited and pooped and cried and kept them up. The downsides are worth it.

So, ask yourself:

Which would bother you more: having the worst of one decision, or having the worst of another?


Try not to speculate!

Avoid imagining “best” or “worst” case scenarios, which is hard because humans have a tendency to imagine bad things as worse and good things as better than they’ll actually be.

Ideally, this should be based on actual experience, and though that’s not always possible, it’s hugely beneficial to get as close to “actual” as you can. Shadow someone, test drive the car, buy a day pass at the potential new gym, babysit someone’s kids… and pay attention.

How do you feel about this?

Leave room for being wrong

Humans are notoriously bad at understanding what will make us happy — even when it’s right in front of our face, only made worse when it’s harder to imagine. Sometimes what we think will make us happy doesn’t.

If you think you have to get it all correct right out of the gate, you’re going to work yourself up into an unnecessary, anxiety-soaked tizzy. Calm down, and rather than demanding The Perfect Decision right off the bat, try something. Experiment, take a stab, see how it feels.

Leave room for changes

The happiest people are those who understand life means change. The unhappiest ones are those who fight it. Short of children, few things are set in stone. And sure, you kinda wanna nail the spouse and career question — or at least get close — but recognize that your role will change within a career, and your relationship will grow and change no matter who you choose.

“What if it’s something big I can’t do-over?”

Then take your time, and really understand a.) what you want (see this post) and b.) how much “fear” is motivating either option — because some of the best decisions are made out of “attraction,” and the worst are made out of “fear.” But also know: no decision is a decision. The universe will just make it for you, which means you live less of your own life.

“What if I still don’t know what I value most?”

Then you are lost, my dear — and I say that gently, because many of us are.

My best tip? Meditation. You’ve probably heard it before, and maybe you’ve tried it (or maybe you haven’t.)

Maybe you think it won’t work, or you think something else holds the answer — but it doesn’t. It’s all in you. And if you can’t access it, it’s because you are lost, and out of touch.

Learning to meditate means learning to sit with yourself — which means that you will gradually be aware of all those quiet vibrations and emotions and physiological reactions we all spend so much time suppressing and stomping down — the same inner workings we then need to guide us for things like this.

Meditate rebuilds that.

“What if I know what to do but just can’t do it?”


I will say: you’re not alone. But beyond that? That’s a different post.