Why People Fail to Make Important Choices

Decision-making is a skill you can practice

Via Lucas Crespo.

Sponsored By: Elle By Respell

Meet Elle, your AI-powered team member that evolves with your processes and data, integrating seamlessly with Gmail, Notion, Airtable, Salesforce, and more. Elle's genius lies in suggesting, building, and executing workflows tailored to your needs. With the capability to create agents and schedule automations, Elle ensures efficiency and is fully SOC-2 compliant. Try Elle now and experience the future of team collaboration. 

PS: Use the promo code PHmagic to unlock the future of teamwork.

As founders, we are constantly faced with choices—where to focus, who to hire, and what direction to pursue. And there are few things worse for a company than a founder who is blocked in making decisions.

Yet making important decisions can be hard. When faced with a choice that might have an existential impact on the business, it's easy to drag our feet and avoid the decision instead of committing to a path and following through.

This was the case in the first company I built, Hacker Paradise, a travel community for digital nomads. My cofounder and I took nearly two years to decide whether to treat it as a side project or a business we were trying to grow.

We tried to make the business financially sustainable, but also shied away from changing it in more substantial ways that might have made it more lucrative (but less fun to run). We worked harder on it than a side project would have warranted, yet focused less on revenue and growth than we would have if we were treating it as a business.

In the end, our indecision made the choice for us. Three years into the business, my cofounder and I burnt out. We had built a nice little business, but one that was shaped more like a restaurant than a startup: we had low margins, and it took a ton of work to run.

At that point, we didn't have the energy to go all in on it as a business, and it was too much work to continue as a side project. So we stepped back and passed the torch onto new leadership.

I’ve observed a similar pattern in friends and clients. From the outside, the avoidance is obvious, and it’s often clear what choice needs to be made. But for the person making the decision, it can still be agonizingly difficult.

Acceptance and commitment therapy (ACT) can help us understand why we get stuck around important choices and how to practice the skill of choosing well. In this piece, we’ll explore the inner barriers to decision-making and how you can unblock yourself to make choices that matter.

Elle by Respell isn't just an AI chat agent; it's a revolution in workflow automation. By learning and adapting to your team's unique processes, Elle makes work smoother and smarter. From generating new workflow suggestions to executing them with precision, Elle is the teammate you didn't know you needed. Its integration with your existing tech stack, like Gmail and Salesforce, means you get a unified, powerful tool at your fingertips. And with Elle's full SOC-2 compliance, you can trust in its reliability and security. Don't miss out on the opportunity to elevate your team's productivity. 

Why we resist choosing 

There are a few reasons why we shy away from making key choices in our work and our lives.

Choice = loss

In his book, Staring at the Sun, psychologist Irv Yalom writes that major decisions can bring up existential anxiety. We feel this way because choices are like a mini-death, where we lose a possibility of what our lives and work might become. 

As Yalom puts it, “For every yes there must be a no, and every positive choice means you have to relinquish others.” If you are unwilling to face the loss that a decision requires, this can lead to procrastination and avoidance.

I see this most often with early-stage founders, who chase overly broad markets instead of making hard choices about who their ideal customer is. When asked who their product is for, they say things like, “Anyone who has a phone,” or, “People who care about their health.” Rather than picking a niche to win and then expand from, they try to be all things to all people.

Even if you have a broad vision for your company, the only way to achieve it is to start with a small and achievable step. Yet choosing not to do everything at once can feel like a loss to a founder, as their fully fleshed-out vision is relegated to the realm of “someday.”

Fear of making the 'wrong' choice

Real choices involve risk. When we make decisions, we open up the possibility of choosing wrong. To avoid the fear of making a mistake, people can end up stuck in analysis paralysis—or simply decide to do nothing, sticking with the status quo by default.

This fear can occur in founders at all stages. At the early stage, people try to think their way to a “right” answer, when what they really need to do is talk to users and get real-world data. At the later stage, founders may hesitate to risk what they’ve already built for an uncertain future, even if that direction might ultimately be better—the classic innovator’s dilemma.

Kodak is an apt example of this. They were the dominant player in photography for decades, holding a strong position in both film manufacturing and camera sales. Despite inventing the first digital camera, Kodak hesitated to make the shift toward digital.

The company was heavily invested in traditional film, and the transition to digital imaging threatened to cannibalize its core business. Eventually, Kodak lost market share to other companies that embraced digital photography, like Canon and Nikon, and filed for bankruptcy in 2012.

Not knowing what you actually want

It’s hard to make a decision if you don’t know what you actually want. You can get stuck in this pattern when you approach decision-making in an overly rational way. 

Logic is important, but “wanting” is an experiential process. A decision can make rational sense, but still feel wrong in your gut. When you approach decisions in an overly analytical way, you lose touch with the emotional aspect of decision-making—which is the part that tells you what you truly desire.

Take job hunting. You can evaluate jobs based on criteria like money, status, or the potential for career growth. But if you’re disconnected from how you feel, you might say yes to a job that looks good on paper—only to realize months later that you hate the day-to-day work.

The same goes for decisions around who to date or what company to start. The logical choice is not always the option that will make you happiest.

Sometimes waiting is reinforced

One reason we procrastinate on major decisions is because sometimes, waiting to get more data really is the right decision. For example, if you’re debating whether to launch a new product, it’s often wise to gather user feedback before diving straight into creating a prototype. This will help you ensure that you’re building a product that people actually want.

However, it’s important to distinguish between procrastinating on a decision and intentionally delaying a choice, because waiting on a decision can kill a company. Consider the case of shipping company Shyp. An attempted turnaround failed because the founders hesitated on the decision to narrow their focus to business customers.

When the founders finally pulled the trigger on this decision, the company started making real revenue—but it came too late. As cofounder Kevin Gibbons wrote in his post-mortem of the business:

"The progress was exciting, thrilling even, to everyone involved with the business—if only we’d made it sooner. Unfortunately, our earlier mistakes had left us with too little runway and insufficient resources to continue pursuing the new direction."

The key is to strike a balance between gathering data and making decisions. And if you find yourself delaying a major choice, make sure you’re doing so intentionally and not just falling prey to avoidance.

How to choose well

In ACT, we see choosing is a skill you can practice. Rather than avoiding decisions or getting stuck in analysis paralysis, you can learn to confront the choices in front of you in a way that allows you to move forward.

Here are a few of the micro-skills that can help you make choices when doing so is hard.

Noticing decision avoidance

The first micro-skill is noticing when you’re avoiding making a decision. To do this, start by paying attention to what you do, think, and feel when you’re avoiding making a decision.

For me, this typically involves rumination. If I’m repeatedly going over alternatives in my head without making progress, it’s a sign that there’s something inherent to the choice that I’m avoiding.

When this happens, I try to drop out of that chain of thought and get a sense of what it is that I’m avoiding. Whether it’s the fear of making a mistake or a loss associated with the decision, noticing and naming what I’m running from often takes the energy out of the cycle of avoidance

Sometimes this alone is enough to unblock a decision. And when it isn’t, it still helps create space for the next micro-skill: connecting with what you really want.

Noticing your desires

We can get so caught up in what others want or trying to make the “right” choice that we lose touch with what we ourselves actually want. So it can be helpful to practice putting yourself in your own shoes and noticing what’s important to you.

To start, notice simple preferences. For example, do you prefer chocolate or vanilla ice cream? Which parts of your job do you enjoy, and which drain you? Who is your favorite band, and how do you feel when you listen to Nickelback?

If you pay closer attention, you’ll notice that each of your responses above corresponds to a felt sense in your body of “like” or “dislike.” If you practice this in daily life, you’ll notice that all throughout the day, you’re bombarded with little tastes of pleasant and unpleasant—things you’re pulled toward and away from.

Noticing this layer of experience is a vital part of decision-making. Through paying attention to your preferences and what you’re intrinsically drawn toward, you are more likely to make decisions that align with what you truly desire.

Practicing willingness

The third micro-skill is willingness—making space for fear and potential loss as you choose a course of action that aligns with what you care about.

One of my clients is six years into her startup, and for the past year and a half she had been considering hiring someone to replace herself as CEO. The company is doing well, but technology has changed a lot in the past half decade, and she has new ideas she wants to explore.

Through our work together, she decided to stick things out at her company. She cares about her team and enjoys supporting them on a day-to-day basis, and has decided to invest another year and see if they can reach the next level of funding or liquidity before bringing in an outside executive.

She knows that by making this choice, she’ll sometimes feel jealousy when she hears other founders talk about the hot new AI tech they’re building and doubt whether she’s being effective in how she uses her time. But she decided she’s willing to experience those thoughts and feelings at times in service of continuing to try to make real progress with a team she loves, even if their business is in a less-sexy space.

You don’t have to practice willingness with big, high-stakes decisions. Rather, you can begin by paying attention to the small choices you make each day and the alternatives they exclude. Over time, you’ll build the muscle memory to make choices that reflect what you truly desire, even when fear and loss can seem overwhelming.

Putting it into practice

Making important decisions is hard, as choices involve risk. However, inaction often leads to worse outcomes than choosing poorly. By practicing the micro-skills above, you can equip yourself for the big choices life throws your way.

To incorporate these in your life, here are a few questions you can use to reflect in times of indecision:

  • What’s the hardest part about the choice you’re sitting with?
  • By saying “yes” to either option, what would you be saying “no” to?
  • When you imagine each option, how do you feel in your body?
  • If no one ever knew what you chose, what would you prefer?
  • What do you think a close friend or family member would say about what would make you happy or content?
  • If you were more willing to experience fear and uncertainty, what might you do?

With practice, you can learn to choose well and free yourself from the cycle of indecision. When the stakes are high, this skill can be the difference between success and stagnation.

So get out there and make some bold choices. Success is not guaranteed, but it beats sitting on the sidelines, waiting for certainty that will never come.

Casey Rosengren is a founder and executive coach based in New York. If you’d like to learn more about coaching, drop him a note.

Like this?
Become a subscriber.

Subscribe →

Or, learn more.

Thanks to our Sponsor: Elle by Respell

Elle is more than just an AI; it's a game-changer for teams seeking efficiency and automation. With its intuitive learning and integration capabilities, Elle stands out as a leading solution in workflow management. Plus, with the free Starter plan available until the end of the year, there's no better time to try it out. . 

Use the promo code PHmagic to unlock the future of teamwork

Read this next:

No Small Plans

The Paradox of Control

Sometimes you need to let go to succeed

3 Sep 19, 2023 by Casey Rosengren

No Small Plans

How to Do Hard Things

A therapy practice helped me face my struggles as a founder

Apr 25, 2024 by Casey Rosengren

No Small Plans

Hack Your Focus With Body Doubling

Get a productivity buddy

4 Aug 22, 2023 by Casey Rosengren

Napkin Math

Crypto’s Prophet Speaks

A16z’s Chris Dixon hasn’t abandoned the faith with his new book, 'Read Write Own'

13 Feb 1, 2024 by Evan Armstrong

Napkin Math

Profit, Power, and the Vision Pro

Will Apple’s new headset change everything?

5 Feb 6, 2024 by Evan Armstrong

Thanks for rating this post—join the conversation by commenting below.


You need to login before you can comment.
Don't have an account? Sign up!
Jennie Pakula 7 months ago

Thanks Casey, this is really helpful. I find it uncanny how often your posts speak to an issue I’m working through!

Casey Rosengren 7 months ago

@JPak -- glad you found it useful!

Every smart person you know is reading this newsletter

Get one actionable essay a day on AI, tech, and personal development


Already a subscriber? Login