12 min read

How to make hard decisions

A practical guide to tough choices.
How to make hard decisions

Hello, grownups!

There's a passage from Sylvia Plath's The Bell Jar that I think about often.

I saw my life branching out before me like the green fig tree in the story. From the tip of every branch, like a fat purple fig, a wonderful future beckoned and winked. One fig was a husband and a happy home and children, and another fig was a famous poet and another fig was a brilliant professor, and another fig was Ee Gee, the amazing editor, and another fig was Europe and Africa and South America, and another fig was Constantin and Socrates and Attila and a pack of other lovers with queer names and offbeat professions, and another fig was an Olympic lady crew champion, and beyond and above these figs were many more figs I couldn't quite make out. I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn't make up my mind which of the figs I would choose. I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet.

The best thing about being young is the feeling that you can still choose to be anything.

This is also, of course, the worst thing about being young.

I'm a pathological life-optimiser, but I'm also somebody who's always struggled making hard decisions. Ending relationships, starting new careers, moving cities... It takes me AGES to think through questions like this. I tie myself in knots thinking through every possible eventuality. I make spreadsheets. I make pros and cons lists. I make mind-maps. And then weeks go by and I realise I still haven't made... a damn decision.

Chidi Anagonye, kindred spirit

After many, many years of patiently listening to me fret over life decisions, my dear friends Meg and Maya suggested this 15-minute TED talk by philosopher Ruth Chang. It's been one of the most valuable ways I've ever spent 15 minutes (thank you, M&M!).

Ruth's talk helped me understand what hard decisions are, and why they're hard. She points out that HARD decisions aren't the same thing as BIG decisions. A big decision is one that has a large impact on your life. But BIG decisions can be EASY: you're offered your dream job, and it's clearly better than your current job; your partner is abusive and you should definitely leave them; Dolly Parton offers you a hug.

A HARD decision is when you have to choose between two different options that are both equally good (usually in different ways). A small decision can be a hard one: which of these two puppies are you going to cuddle first? IMPOSSIBLE CHOICE because every puppy is perfect. But of course, hard small decisions don't matter very much. It's BIG and HARD choices that really drive you crazy.

So, the first thing to do when you're feeling vexed over a BIG decision is to work out whether it's actually a HARD decision. Sometimes, a decision feels hard only because you don't have enough information about it. It's a decision that does have an objectively better answer, you just might not know what that answer is. Choices like, "should I buy this house" often become easy to after you do a bit of research and thinking. Choices like, "should I marry this person" usually don't.

Making big decisions easier

Chip and Dan Heath's book Decisive is a great playbook for making BIG decisions EASIER. They outline four traps we tend to fall into when making decisions:

  1. Narrow framing: we view a decision as a choice between two things, when actually there might be other options we're not considering.
  2. Confirmation bias: we pre-decide something, and then only notice information that supports the beliefs we already have.
  3. Short-term emotions: we place too much emphasis on how we feel in the moment, and too little on the long-term ramifications of a decision.
  4. Over-confidence: we think we can predict the future better than we can.

If you ever notice that you're trying to choose between competing options, and it feels hard, that might be because neither option is good enough. A big part of making choices is creating new options for yourself. We often fall into the trap of thinking that decisions are all-or-nothing, when actually a little bit of something might be the best outcome for you.

As an example: what if you've got a job that pays the bills but your real passion is teaching parrots to yodel. Should you quit your job to focus full-time on your yodelling parrot choir? Well, those aren't your only two options. You could try renegotiating your job down to a four-day work-week, or you could get a different job that involves more parrots than your current job. Don't get stuck looking only at the options right in front of you, you might miss some better ones in your periphery.

You can also make some decisions easier by gathering more information about your options. It can help to actually write down your assumptions, and then go and do some research and check whether they're true. Most big decisions benefit from a few hours of research! Like, if you're trying to choose what to study at university, you might want to look up the average post-graduate employment rates of people with those degrees. If you're stuck in a decision with your partner, maybe you need to drag yourselves to couple's therapy and make sure that their views on a matter are actually what you assume they are.

We are hopelessly bad at forecasting how we'll feel in the future. Address that by speaking to real people who've made similar decisions in the past and ask how they feel about their decision now. Reddit can be a great place to ask anonymous questions of people in unusual careers, or who have been through similar situations to you. Even better: if you can, try taking your options for a test-drive. If you're considering a new job, ask if you can work on contract there for the first month to see if it's a good fit for you; if you're thinking of moving somewhere, go on a holiday there first.

Try, as much as you can, to ignore short-term feelings when making long-term decisions. Don't NOT break up with somebody you should break up with because the immediate process of breaking up with them sucks. Don't NOT quit a job because you'll feel bad for disappointing a kind boss. They'll get over it. You'll get over it. The outcome you'll be left with matters more.

Combat confirmation bias by actively looking for the counter-points to your assumptions: ask your most sensible businesswoman friend if they think you should take a job at an NGO; ask your most romantically cynical pal if you should get married. You're not letting other people tell you what to do, you're just making sure you're seeing the whole picture.

Lastly, understand that few decision are forever, and it's healthy to learn more about a decision later and decide it's no longer right for you. I'm a big believer in actively setting up deadlines to review big decisions a few months down the line. The Heaths call this "setting a tripwire". It's important to do this, because all of us are guilty of the sunk-cost fallacy, where we tie ourselves to poor decisions because we don't want to "waste" the time/resources we already invested into them. I do this by literally setting a calendar entry a few months after I make a big decision reminding myself to reassess it, and ask myself if it is still what I want to commit to. That's how you prevent a bad decision from becoming a life-alteringly bad decision.

So, a quick action plan for making a big decision easier:

  1. Brainstorm alternative options.
  2. Make a list of actions you could take to get more information about your options (e.g. look up questions online, ask people who've made a similar decision, seek out counter-views, "test-drive" the options, make a spreadsheet).
  3. Ask yourself how you might feel about this 10 minutes, 10 months, and 10 years from now. Try to ignore your short-term feels as much as you can. Another way to get distance from your emotions is to ask yourself: "what advice would I give to my best friend in this situation"?
  4. Set an appointment with yourself sometime in the future to review your decision (put it in your calendar).

Often, you'll find that if you go through these steps, what looked like a difficult choice is actually a perfectly easy one: there is an option that is clearly better than the others.

Don't spend too long trying to make a decision. You will never be able to perfectly predict the future, and you'll drive yourself nuts trying. As Oliver Burkeman puts it, "The future will never provide the reassurance you seek from it." Do your best to choose well, but don't dither forever.

What do to with hard decisions

But here's the deep shit, friends: sometimes you'll be confronted with a choice that can't be made easier. No amount of research or thinking will give you an objectively better option. These are the truly hard choices, and they are the most important ones you'll ever make.

Like many people, I had a dramatic quarter-life career crisis in my mid-20s. I hated my job and I wanted to do something else. I went through all the steps above: I found alternative choices, I filled a whole notebook with research about my options. I invented an elaborate system where I rated each option against a list of weighted priorities, hoping that I could just get a score that would tell me what I should bloody do with my life. TELL ME WHAT TO DO, NUMBERS!

Oh sweet, foolish 20-something Sam.

I dug up this notebook the other day, and was just overcome with affection for the confused dolt who wrote all this.

I was approaching it like a problem to be solved, a question that had an objective correct answer that I just needed to find. In other words, I was treating a hard decision like an easy decision.

But of course, some decisions have no objectively best choice. Some decisions are a pure act of will, of self-determination.

Often, with hard decisions, your options are good in different ways. They support different values that you have. But how do you rank the values themselves? There is no external or objective way to do that. All that's left is you: what kind of person you want to be, what kind of life you want to live.

Human beings are excellent rationalisers. We're great at coming up with reasons that explain the choices we made, even though those were often not the actual reasons we made the choice. When a choice is hard, you have the power to create good reasons for either choice. You get to author the story of your life.

This is where Ruth Chang's work was so helpful to me. Ruth points out that moments like this few, and that each one is a gift.

It’s here, in the space of hard choices, that we get to exercise our normative power, the power to create reasons for yourself, to make yourself into the kind of person for whom country living is preferable to the urban life. When we choose between options that are on a par, we can do something quite remarkable: we can put our very selves behind an option. Here’s where I stand. Here’s who I am. I’m for banking. I’m for chocolate donuts. This response in hard choices is a rational response, but it’s not dictated by reasons given to us. Rather, it’s supported by reasons created by us. When we create reasons for ourselves to become this kind of person rather than that, we wholeheartedly become the people that we are ... You become yourself through hard choices. Hard choices are precious opportunities to celebrate what’s special about the human condition. That’s why hard choices are not a curse, but a godsend.

You can't make a hard choice using the strategies that help you make an easy choice. You have to just... make it. And then you have to live with the choice that you made.

Ultimately, the best exercise I've found when making a hard choice is this: tell the story of your life, having made one decision. I like to have these long imaginary conversations with myself while I'm out walking (pro-tip: put headphones on so people don't realise you're talking to yourself, like a WEIRDO). Try explaining to an imaginary person how your life brought you to the point where you had to make this choice, and then why you made the choice you did. Now, do the same thing with the other choice.

Which of those stories do you want to live with?

You get to choose.

The tie-breaker

Okay okay okay, are you still ENTIRELY CONFUSED? Here's one last rule of thumb for times when you've thought through a choice in detail, and you STILL don't know what to do, from Oliver Burkeman. The tie-breaker.

When stumped by a life choice, choose “enlargement” over happiness. I’m indebted to the Jungian therapist James Hollis for the insight that major personal decisions should be made not by asking, “Will this make me happy?”, but “Will this choice enlarge me or diminish me?” We’re terrible at predicting what will make us happy: the question swiftly gets bogged down in our narrow preferences for security and control. But the enlargement question elicits a deeper, intuitive response. You tend to just ”know” whether, say, leaving or remaining in a relationship or a job, though it might bring short-term comfort, would mean cheating yourself of growth. (Relatedly, don’t worry about burning bridges: irreversible decisions tend to be more satisfying, because now there’s only one direction to travel – forward into whatever choice you made.

Wishing you hard choices, yodelling parrots, and growth,


Spring is coming!

Updates from Sam-Land

Somehow, loves, I survived the Winter of Weird. And boy, was it weird. We're still in strict lockdown here in the UK, but it's amazing how much better everything feels now that the days are getting longer and brighter, buds are appearing on trees, and seeds are poking hesitant sprouts up through the soil.

"Weird" was a pretty successful theme for winter: it helped me choose books I wouldn't have chosen, films I wouldn't have watched, games I wouldn't have played, activities I wouldn't have tried. I don't think it was as emotionally rejuvenating as I'd hoped it would be, but that miiiiight have had something to do with the fact that I've been imprisoned in my house since October during a pandemic, who knows!

I haven't decided on a new theme for spring yet. I've been thinking about something like The Spring of Amateurism, because I'm working on a creative project that's pushing me far outside of my comfort zone, and the imposter syndrome is strong! I'd love to be planning the Spring of Going to South Africa and Giving All My Friends and Family a Giant Bloody In-Person Hug, but that's probably not on the cards just yet :)

Whether you're going into spring or autumn (the best season), I'm beaming you a big virtual hug anyway.

Recent lovely things:

  • Sara Gran's City of the Dead, a mystery novel about an esoteric detective. It didn't quite work for me as a mystery, but it slapped as a portrait of post-Katrina New Orleans.
  • Paul Tremblay's A Head Full of Ghosts. Horror novel about a teenage girl who might be possessed by demons or might be suffering from schizophrenia. Absolutely brilliant; one of my favourite novels of the year so far.
  • Austin Kleon's Show Your Work, a book for people who hate the very idea of self-promotion but have to do it anyway. It's excellent, and Austin's blog is one of my favourite places on the Internet.
  • The 2013 documentary Fire in the Blood, which is on Netflix. It's about how pharmaceutical companies and Western governments intentionally obstructed access to life-saving antiretrovirals during Africa's HIV/AIDS crisis, leading to the completely avoidable deaths of approximately ten million people. It is devastating, enraging, and all-too-bloody timely, considering the vaccine inequality unfolding again around the world right now.
  • The teen horror-romcom movie Spontaneous, recommended by my friend Dale, which is about teenagers that start spontaneously exploding, and is much more poignant than you'd expect it to be.