I’ve been having a lot of conversations about decision-making lately. How I knew I was ready to have a baby. How I ended up doing the work I do. Why I started writing and how I keep going. It’s not that people think I have my life figured out—I think we just like asking each other how things happened. There’s something comforting about hearing someone else’s version of “and then I just did it.”
We’re obsessed with the “how” of things. How to get rich, how to find your passion, how to parent without completely screwing up your kid, how to be productive, healthy, attractive, happy. I ask Google and ChatGPT these questions.
I ask people I know. Sometimes I get great answers. More often, I get something that sounds good but doesn’t quite fit when I try to apply it to my actual life.
What I’ve learned (and what I’m still learning) is that there are a few approaches that work for me. Not because they’re universal truths or because I’ve cracked some code, but because they help me move forward instead of staying stuck. So here they are, documented in my little corner of the internet for anyone who stumbles across them.
This is written for my peers. All my love to them.
The perfect choice vs. perfecting the choice you make
the idea of a “correct” choice is mostly fiction. Take a classic scenario—you have two job offers. One keeps you close to home with all the familiar comforts but limited growth. The other means moving to a new city, lots of potential, also lots of uncertainty and starting from scratch.
There isn’t a right answer here. There’s just a set of trade-offs, and you’re the only one who can weigh them. What makes this liberating, once you accept it, is that your choices become “right” by virtue of you committing to them. By showing up. By not bailing when it gets hard. By creating value and learning from what works and what doesn’t.
When I decided to move to Goa, I knew I’d never find a traditional job here. Like, a Goa-based job I could commute to. Given what I do and the industry I’m in, there just isn’t much here. So I moved knowing everything I did from that point forward would need to be remote. I’d have to be okay with that. I’d need to get better at presenting my work online, building relationships through a screen, being visible in ways that felt uncomfortable.
And I have. I’ve switched industries more than I expected. I’ve leaned into creative work. This blog has become part of my professional identity, which is something I never imagined when I started it. Did I make the “right” career decision? I don’t know. I’m not sure that’s even the question. What I know is I’m actively making it right by continuing to show up for it.
So now when I’m faced with a big decision, I try to remember: it’s less about the choice itself and more about what you’re willing to do with it afterward. You can’t really make a “wrong” choice if you’re committed to learning from it and adjusting as you go.
Escaping the how-trap
I’ve noticed that the most inspiring answers rarely come from asking how.
How did you manage to do that? How did you find the time? How did you get your kid to sleep through the night? How did you figure out your career path? It feels like the logical question to ask when you’re stuck. If someone else did it, I’m sure they can tell you the steps, right?
Wrong. Or at least, wrong-ish.
The internet is FULLL of people telling you how to live your life. I’m literally doing it right now (the irony isn’t lost on me). There’s so much clout in being The Person Who Figured It Out. They’ve got so much advice!!! I’m not saying we gain nothing from these answers. But here’s what I’ve realized: the answer to “how” depends on a thousand factors we can’t control. Timing. Circumstances. Luck. Who you know. What city you live in. The economy. Your health. The health of those you care for.
No one’s life will ever line up perfectly enough for their path to look like yours. And here’s how I know the “how” doesn’t actually matter that much: there’s nothing I find more inspiring than when people say, “If you told me a year ago my life would look like this, I wouldn’t have believed you.”
That statement is so alive! It means THEY had no idea how either. And yet here they are. They did the thing without a roadmap, without certainty, probably while feeling like they were completely winging it.
That’s the good stuff. That’s what proves things can change. That’s how we know we’re more capable than we think. That how we know that we can get what we want, even when we don’t know the exact steps.
Guesswork sometimes is the bestwork
Guesswork doesn’t get enough credit.
If our own decisions are sometimes just educated guesses (and let’s be honest, they usually are) why do we look at other people’s successes and hope for a clear roadmap? We forget that those paths only look clear in hindsight. When they were in the middle of it, they were probably just as lost as we are.
I find it comforting to know that others are dealing with what I’M currently dealing with, without perfect information. Especially as a parent. Millennials and Gen X are the first cohorts of parents doing this alongside the internet. We’re subject to endless amounts of advice, opinions, and pros and cons for every single decision.
What should you do about screen time? Social media? Sleep training? Food? Discipline? Schooling? Every choice you make for your kid can be questioned, optimized, or criticized by someone online who swears they have the answer. The information overload can be paralyzing. You’re making decisions every single day about another person’s life, and there’s always someone ready to tell you you’re doing it wrong.
Now I’m not saying DON’T get advice. I’m not saying don’t learn from others. Asking how can spark curiosity, give you useful insights, help you solve concrete problems. But it’s important to recognize when the quest for answers becomes a trap. When you’re endlessly scrolling through parenting groups, taking online courses, and following people who promise some formulaic path to success.
At some point, you just have to trust yourself and wing it. Make your best guess with the information you have, and commit to adjusting as you go.
Decisions need follow-through, not just good intentions
Making a decision is just the beginning. The real value comes from what you do next.
There’s often this post-decision hangover filled with doubt and second-guessing. Did I make the right choice? Should I have done something differently?
You’ve got to wear in your decisions like new shoes. At first they feel wrong, uncomfortable, maybe even painful. But with time, if you keep living in them, they start to feel more natural. More right.
And nobody gets there overnight. You have to decide on something, and then very shakily followed through. Over and over. Less shakily each time. That’s how it works. You commit, you act, you stumble, you keep going.
You can clap for someone who has made a great decision all day long, but without action, it’s just unrealized potential. It’s a nice idea that goes nowhere.
Regret is an okay thing to feel
Nearly all my good decisions have some regret attached to them. There, I said it.
There are no perfect decisions that lead to a perfect life. That’s not how any of this works.
I had a baby before I turned thirty. It was something I always wanted. And I mean genuinely, deeply wanted. But it also comes with regret. I missed out on some experiences that you can only really do in that sweet spot of late twenties-early thirties. The spontaneous trips. The reckless career pivots. The freedom to be completely selfish with my time.
I don’t think this should be controversial, but somehow regret has gotten a terrible reputation. Like if you feel any regret, it means you made the wrong choice. That’s bullshit. If I think long enough about any decision I’ve made, I can find something to regret about it.
I can’t fault myself for not having all the answers when I made these decisions. I can’t expect myself to have predicted every possible outcome. What I can do is accept that both positive and negative feelings. The joy and regret, the satisfaction and loss. These feelings will accompany most meaningful decisions. They’re part of the deal.
My job isn’t to have zero regrets. My job is to manage the regrets I have, make peace with the trade-offs, and keep moving forward anyway.
The thirties so far (all six months of them) have given me a bit more perspective than my twenties did. But absolute certainty is completely out of reach.
I can only make choices with the wisdom I currently have. Apparently I’ll gather more as I go along, so I guess things are looking up.
Over-optimizing is a useless exercise
When I first moved to Goa, I was so excited about living near the beach that I decided I HAD to go a certain number of times per week. I made a plan to go 30 times before turning 30. I took something inherently joyful and spontaneous and turned it into a checkbox on my to-do list.
I turned fun into a chore. I’m very good at this, btw.
Don’t get me wrong—I completely understand putting routine into things you want to prioritize. I have a writing routine because I don’t believe in waiting for inspiration to strike. Structure is necessary. But too much rigidity kills the thing you’re trying to nurture.
After nearly three years of living here, I go to the beach when it feels right. Sometimes once a week, sometimes once a month. But every single trip is more memorable than when I forced it. I’m more present. It always feels like I’m in the right place at the right time, like I got lucky catching that particular sunset or that perfect wave of fresh air on a day when I really needed it.
I don’t have concrete plans or schedules for beach days anymore. I just stay open and willing to enjoy them when they come. That’s enough.
Lessons arrive when you’re ready (not before)
You can’t learn the lesson until you’re ready to learn it. This is why we find ourselves stuck in the same patterns, ignoring good advice, walking straight into the same problems we swore we’d avoid this time.
The lesson is out there, waiting. But we have to catch up to it first. As Tolstoy put it, “Truth, like gold, is to be obtained not by its growth, but by washing away from it all that is not gold.”
Learning lessons has been a process of stripping away everything that isn’t essential. Sometimes that process takes forever. Sometimes I have to go through the same experience multiple times before the lesson finally sticks.
This has been especially true with friendships. I have this naive tendency to see people the way I want to see them, not as they actually are or as they present themselves to me. I ignore red flags. I make excuses for behavior I’d never tolerate from strangers.
My friend told me over and over: when people show you who they are, believe them. And yet I rarely did. I had to learn this lesson again and again. Maybe I’ve finally learned it, though I’ll never really know until I’m tested again. Maybe it took me a decade too long. Maybe that’s fine. I’m wiser for it now.
The point is, you can’t force yourself to learn something before you’re ready. You just have to trust that when the time is right, the lesson will land.
Impermanence is a nice thing
Most (most!!!!!) decisions aren’t permanent. In fact, very little in life is permanent.
Most of it is a sequence of temporary phases, each like a window that opens for a while and then closes. These phases could be anything: the early days of being a parent, switching careers, moving somewhere, or starting a new relationship or a business.
Each phase has its own set of experiences and challenges, but the common thread is that they’re all temporary. The ‘newness’ is temporary, and the difficult starting phase is temporary. Some phases have a clear end, while others are more open-ended.
During tough times, it’s comforting to remember that things will change, and new phases will begin.
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Okay, those are the decision-related thoughts I’ve gathered this year.
I’m trying to practice them, especially now as I struggle to make sense of the world we’re living in. I find myself questioning whether wisdom even matters, whether any of these thoughts hold up in light of the appalling things happening around us.
There’s too much I don’t understand. Too much I don’t want to accept. Too much that makes everything else feel small and pointless.
These are strange times. Hang in there.
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