The first month of 2023 flew by and after doing a quick end-of-month reflection, I’ve concluded on a sincere but mundane assessment—life’s pretty good! As always, I feel like I could be having more of an impact at work and outside of it, but overall I feel really good about my relationships, engaged in my hobbies, and excited for the rest of the year.

There’s a lot to be grateful for and I’d like to think it’s because I've made a series of good choices.

I tell myself I’m a good decision-maker but I also acknowledge hindsight bias makes that statement hard to evaluate objectively. I can’t ignore how impactful it’s been to end up being at the right place at the right time and around the right people. We do the best we can but oftentimes our lives are largely dependent on factors we can’t control.

I’ve been thinking about that a lot lately. If it’s possible to make good decisions and still fail or bad decisions and still succeed, how would I even know I’m making good choices? How do I actually improve as a decision-maker when there are so many factors that convolute our judgment both during and after the decision’s been made?

If we could graph every decision along some personal utility curve with discrete probabilities and expected values for each outcome, life would just be one big math equation I can solve on my window Beautiful Mind style. 

It’s too bad that we’re influenced by hard-to-quantify things like our emotional state, our identities, and our unconscious biases.

But I’m convinced there are still tangible ways to make better choices. We can adopt processes that mitigate the capriciousness of our emotions, mindsets that ease our anxiety with uncertainty, and habits that ensure we’re progressing toward our goals.

I’ve explored some frameworks in the past but I haven’t yet reflected on how I personally make decisions.

What are some of my tendencies? What areas do I struggle with? And what are concrete ways I plan to actually improve my decision-making process?

If our lives are just a collection of the choices we make, I think we all stand to benefit from figuring out answers to those questions.

Ceding responsibility

I often find myself as the designated decision-maker at work and the stakes can range from something fairly benign like "What happens after someone clicks this button?" to something more substantial like "What does everyone spend time working on this year?"

As someone with a tendency to people-please, I’ve undoubtedly made these decisions based solely on how others were feeling.

Empathy and collaboration are critical ingredients for good decisions, but there’s also a fine line between incorporating other perspectives versus making decisions purely to keep others happy.

When I get in that mode, I seldom pause to ask the surprisingly difficult question: “What do I actually believe?” 

Instead, I put the decision to a vote or I just listen to my manager or I just mindlessly apply some previously-used, agreed-upon procedure. None of these behaviors are necessarily bad on their own, but when done mindlessly, we give up ownership of the actual decision. 

We relinquish agency whenever we lack confidence in our own decision-making process. Going with the flow is often easier than pressure-testing our assumptions or engaging in productive debate. 

By spreading responsibility to other people or another process, we also detach ourselves from the outcome. When things go wrong, we have a ready-to-use excuse: Hey, it wasn’t my fault…I did what I was supposed to do!

We need to take responsibility for our decisions and it requires a level of self-assuredness especially if that decision goes against the grain.

One of the best pieces of advice I’ve ever received is to “show your work” when making decisions much like what our math teachers tell us to do. You articulate what you’re trying to solve for, you lay out what assumptions you hold, and then walk everyone step-by-step through your reasoning.

You bring people along with you in your decision-making process, forcing yourself to follow a logical train of thought while also inviting feedback to reinforce your thinking. 

It’s also much easier for others to buy in when they know what went into the decision in the first place.

Because people understand the inputs behind a recommendation, you’re able to debate and discuss those inputs rather than relitigating the entire proposal.

“Let’s eat here because it’s close to work” seems much more reasonable than demanding “We’re going to eat here”. Maybe being near the office isn’t the right criterion and my friends would actually prefer a place with an excellent happy hour.

By doing this, you get the benefits of collaboration while maintaining the intellectual rigor of owning your decision. 

Punting decisions

But I’ve also been guilty of being overly rigorous in making a decision. The type-A perfectionist in me is deathly afraid of making a mistake so I push off making a decision.

That idle time isn’t usually spent thinking critically. Most of the time, I’m quietly hoping the situation can resolve itself or I convince myself that what’s happening isn’t so bad.

Meanwhile, I tell the team we need more data. I tell my friends that I’ll think about it. I tell myself that I’ll decide when the situation feels right.

But doing nothing is still a choice. Every moment I defer a decision is an explicit choice to keep things the way they are. When I say I’m not ready to decide, what I’m really saying is “I am choosing the status quo.”

I recently learned about this decision-making philosophy from Toby Lutke that really resonated with me: 

If we’re meeting to solve a problem, we are not allowed to walk out of this meeting without deciding to change something. Because if the problem really exists right now, keeping the status quo clearly won’t solve it.

- Toby Lutke (paraphrasing)

Indecision has a real cost. It not only leaves the problem unresolved but also creates additional anxiety and uncertainty for yourself and those around you. We should ask ourselves whether that additional time or incremental data point outweighs the benefits of taking decisive steps and building momentum toward a plan.

I've been thinking a lot more about how I can make decisions faster even if it means I'm wrong more often. Unless the consequences are going to occupy a lot of my attention for the next few months—like a major personal or financial decision—I'm likely able to reverse what I decide.

I'm better off acting now, gathering feedback, and then change course if necessary. I can ride the momentum of making progress rather than carrying the emotional burden of waffling back and forth.

And we also shouldn't shy away from tackling the riskiest parts of our plan first. If your goal was to teach a monkey how to recite Shakespeare on a pedestal, you’re better off figuring out how to teach a monkey to read first before building your pedestal.

It’s easy to push decisions off. It’s easy to keep the status quo. And it’s easy to just do things you know how to do. But they’re not what moves the needle in terms of achieving your goals. Don't waste time doing what's easy when success is going to come from the hard stuff. 

Biasing towards action. Failing fast. Maximizing shots on goal. Whatever you want to call it, I think most of us can benefit from making more decisions faster.

Doubling down

Speaking of goals…deciding what we choose to pursue might be some of the most important decisions we make in our lifetime. 

We set out to achieve things based on what we personally value. Maybe we run a marathon because we value doing hard things or we start a non-profit because we think others could benefit from it. 

We also tend to make our goals pass-fail in nature. Once we’ve decided what race we want to run, we're failures from the time we cross the starting line until we finally reach the finish line. Getting to that destination becomes our sole focus and so we put our heads down and start grinding away.

Grit and perseverance make it possible for us to achieve incredible things, but they can also lead us astray when we forget why we're even pursuing the goal in the first place. 

As someone who takes pride in being able to make things happen, I've certainly been guilty of this. Whether it’s launching a project, selling someone a point of view, or hitting a certain metric, fulfilling that milestone becomes all-consuming. 

I develop a vision for how this journey needs to go and I’m determined to bend reality to my will. My point of view becomes a treasure to be preserved at all costs rather than a hypothesis to be tested. 

Every challenge or contradicting viewpoint becomes just another obstacle to overcome rather than new inputs for me to reevaluate.

My self-worth gets tied to crossing the finish line and my decisions become fixed events even as all the inputs that led to that decision evolve.

I'll often justify my lack of flexibility with those classic sunk-cost fallacies.

“We’ve come too far, let’s just finish it.”

“We said we were going to do it so we’re going to do it”

“I’m not going to be a quitter”

When achievement is at the forefront instead of the original intent of a particular choice, we lose that self-awareness, curiosity, and flexibility that’s so critical in consistently making good decisions.

It’s why defining milestones ahead of time is so important.

You’re not just breaking down a seemingly insurmountable task into more manageable chunks, you're recalibrating your definition of progress and success. 

When success isn’t purely defined by one hyper-specific end result, we won’t feel like we’ve wasted our time and energy if things don’t turn out according to plan. As a result, we’re much more nimble decision-makers—more willing to reassess, change direction, and objectively grade our thought process.

I’m also a big fan of attaching due dates to your milestones because it forces a natural point of reflection. We make decisions with a given set of inputs and if progress isn’t materializing at the rate we expect, it’s likely something has changed.

Instead of pressing on, we can re-evaluate whether or not the conditions for success still hold. Was one of our original assumptions incorrect? Was there an input we didn’t consider? What’s true today that’s no longer true when we constructed our plan?

Being willing to pivot doesn't mean we quit every time something gets hard. It means we constantly evaluate whether we're striking the right balance between conviction and open-mindedness. 

Closing thoughts

So I'll admit a lot of what we just discussed can appear to be contradictions of one another.

We should be rigorous when weighing decisions. But not so rigorous that we’re slow and indecisive. But don’t be so decisive that you’re not willing to change course.

That’s why being a good decision-maker is really hard! There’s no playbook with set instructions to apply to every situation. I'm convinced every good decision-making process has elements of rigor, speed, and flexibility but we need to figure out for ourselves how to balance them in each situation. 

What we explored obviously wasn't exhaustive, but they are—at least for me—tangible ways I hope to improve my own decision-making. 

It's a lifelong journey. I have a long way to go. But I’m excited to continue working on this in the years ahead.