What If It's Ok That Making Decisions Is Uncomfortable?

How to stop fighting uncertainty, overthinking your options, and second-guessing yourself.

I've been having a lot of conversations about decision-making lately.

One client has a big decision to make, and she's frustrated that the answer isn't coming as quickly as she'd like. She's trying to be patient, but the uncertainty is making her anxious. She wants to know what to do, and she wants to know now (relatable, no? 😅).

Another client recently made a decision after doing a tremendous amount of research, weighing her options, consulting people she trusts, and checking in with herself about what she really wants.

She felt good about her choice.

And then she started second-guessing it.

As we talked, she described how exhausting the entire process had been. All the thinking and analyzing beforehand. The pressure to make the right choice. And then, even after deciding, the nagging question of whether she'd gotten it wrong.

She wanted to know how to make decisions with more ease.

And it got me thinking.

What if part of what makes decision-making so difficult is our expectation that it shouldn't be?

What if we're making an inherently uncomfortable process even more uncomfortable by fighting the discomfort?

Why does making a decision feel so hard?

Think about what we're actually doing when we make a decision.

We're choosing a path forward without knowing exactly where it will lead.

We're working with incomplete information, trying to anticipate future circumstances, and weighing possibilities that may involve competing needs, values, and desires.

Even when we've done our research and thought things through carefully, there's almost always something we can't know.

Will I enjoy this new job?

Will this relationship work out?

Will I regret moving?

Will I be happier if I leave?

Will this business idea succeed?

We can make educated guesses. We can gather information. We can talk to people who've been there.

But we can't know the future.

And for many of us, not knowing feels really uncomfortable.

Our brains are constantly trying to predict what will happen next. Uncertainty can register as a potential threat, particularly when a decision involves something important to us.

So we try to resolve it.

We research. We analyze. We make pros-and-cons lists. We ask friends for advice. We imagine every possible outcome.

And sometimes, all of that is genuinely useful.

But sometimes we're no longer gathering information to make a thoughtful decision.

We're trying to make the uncertainty go away.

That's a very different project.

When thinking becomes a way to manage anxiety

I'm a big believer in thoughtful decision-making.

In fact, I've written before about why we shouldn't dismiss careful analysis as a problem. Some of us naturally process decisions by gathering information, examining possibilities, and thinking things through.

There's nothing inherently wrong with that.

The trouble begins when our thinking stops helping us understand our options and starts functioning primarily as an attempt to feel certain.

Maybe you've experienced this. You spend an hour researching something and feel better because you've learned something useful. But the next day, the anxiety returns.

So you do more research. You revisit your pros-and-cons list. You ask another friend what they think. You mentally rehearse a conversation you've already imagined twenty times.

And for a little while, you feel some relief. Until the doubt creeps back in.

The problem is that you're asking your thinking mind to do something it can't actually do: eliminate uncertainty about the future.

And no amount of thinking can guarantee that you'll never experience disappointment, regret, or an unexpected outcome.

One question I often find helpful is: Am I thinking about this because there's something useful left to learn, or because I'm uncomfortable not knowing?

There's no judgment in that question. It's simply an invitation to notice what's happening.

Because if what you really need is support tolerating uncertainty, another three hours of research probably isn't going to give you that.

The discomfort of uncertainty—and the discomfort we add

Here's where I think things get particularly interesting.

There's the discomfort of not knowing what to do. And then there's the discomfort we create by believing we should know what to do.

Think about the difference between these two experiences.

I'm facing an important decision, and I'm feeling anxious because I don't know how things will turn out.

Versus:

I'm facing an important decision, and I'm feeling anxious because I don't know how things will turn out. Why can't I figure this out? What's wrong with me? Why am I taking so long? I should be better at making decisions.

The first experience is uncomfortable. The second is often downright miserable.

Because now, in addition to navigating uncertainty, you're criticizing yourself for struggling with it.

This is something I see frequently in my coaching practice. People don't just want to make a good decision. They want to make it quickly. Confidently. Without overthinking. Without anxiety. Without regret.

And when their actual experience doesn't match that ideal, they decide they're doing something wrong. But what if they're not?

What if feeling uncertain, anxious, or conflicted doesn't mean there's something wrong with your decision-making process?

What if it just means you're a human being making a decision that matters to you?

Sometimes you actually need more time

I want to be careful here, because I don't think the answer is always to stop thinking and just make the decision already.

Sometimes we genuinely need more information. Sometimes we're weighing competing values, and it takes time to understand what matters most. Sometimes we need to have a difficult conversation, explore an option, or see how circumstances unfold. And sometimes we need to let an idea sit for a while.

Have you ever struggled with a decision, stepped away from it, and discovered a few days later that something had shifted?

Maybe you saw the situation differently. Maybe a preference became clearer. Maybe you realized that something you'd been treating as essential wasn't actually that important.

Not all clarity comes from actively working on a problem. Sometimes it emerges when we give ourselves space.

But if we're constantly telling ourselves that we should have figured it out by now, we make that waiting period much harder than it needs to be.

Instead of asking, Why is this taking me so long?, we might ask: What if this is simply how long this particular decision needs?

Of course, there's a difference between allowing clarity to emerge and indefinitely postponing a choice because we're afraid to make it.

Which brings us to another useful question.

How do you know when you've thought about it enough?

I use a simple framework in my coaching practice that I call Clarity + Capacity + Courage.

It's a way of thinking about what we need in order to move forward.

And I think it's especially helpful when we're feeling stuck in a decision.

Clarity: Do I know enough to choose?

Notice I didn't say, Do I know everything? Because that's usually impossible.

Instead, ask yourself:

• Do I understand my options and their likely consequences?

• Do I know what matters most to me?

• Is there specific information I still need that could meaningfully change my decision?

If the answer to that last question is yes, perhaps you have more exploring to do.

But if you've already gathered the relevant information and you're simply revisiting the same questions, more thinking may not help.

Capacity: Do I have what I need to navigate this decision?

Sometimes the issue isn't a lack of clarity. It's that we're exhausted, overwhelmed, or dealing with too many other demands. Our capacity matters.

Ask yourself:

• Do I have the emotional and practical resources to make this decision right now?

• Am I so activated by anxiety that I'm having trouble thinking clearly?

• What support would help me navigate the decision and whatever comes afterward?

Maybe you need to talk something through with someone you trust. Maybe you need to take a walk, get some sleep, or step away from the decision for a few days. Maybe you need to build a financial cushion or create a contingency plan before moving forward.

Supporting your capacity isn't the same as avoiding the decision.

Courage: Am I willing to choose without a guarantee?

Sometimes we have enough clarity. We have enough capacity. And we're still waiting. Waiting to feel completely confident. Waiting for the anxiety to disappear. Waiting for some unmistakable sign that we're making the right choice.

But what if that feeling never arrives? At some point, making a decision may require us to acknowledge that we can't eliminate all uncertainty. We can only make the most thoughtful choice available to us with what we know right now. And then see what happens.

That's not recklessness. That's courage.

What if you made room for the discomfort?

One of the things I teach in my coaching practice is how to relate differently to uncomfortable thoughts, feelings, and sensations.

Our instinct is often to get rid of them. We want the anxiety to stop. We want the fear to disappear. We want to feel calm, confident, and certain. But sometimes our attempts to get rid of discomfort are exactly what keep us stuck.

What might happen if, instead of trying to eliminate your decision-making anxiety, you made a little room for it?

You might start by noticing what's happening in your body. Is your chest tight? Is your stomach churning? Are your shoulders creeping toward your ears? Can you take a moment to feel your feet on the ground, look around the room, and allow your body to settle a little? Then, instead of immediately trying to solve the decision, get curious.

What am I afraid might happen?

What am I trying to protect myself from?

What would help me feel supported right now?

And perhaps most importantly: Can I allow myself to feel uncertain without interpreting that uncertainty as a problem I need to solve immediately?

This isn't about forcing yourself to be comfortable with something that feels uncomfortable. It's about learning that you can experience discomfort without needing to make it disappear. And when we stop spending so much energy fighting our feelings, we often have more capacity available for the actual decision.

What about after you've made the decision?

Unfortunately, making a decision doesn't necessarily make the uncertainty disappear. Sometimes we finally choose a path, feel a moment of relief, and then immediately start questioning ourselves.

What if I should have chosen the other option?

What if I overlooked something?

What if this turns out to be a mistake?

And off we go again.

But second-guessing yourself doesn't necessarily mean you've made a bad decision. Sometimes it simply means you're still uncomfortable with uncertainty.

You made a choice, but you still don't know how it's going to turn out. And now that you've committed to one option, you're more aware of the possibilities you've left behind.

That can be uncomfortable, too. When this happens, I think it can be helpful to ask:

Do I have new information that genuinely warrants reconsidering my decision? Or am I experiencing a new wave of anxiety about the uncertainty that was already there?

If something meaningful has changed, by all means, reconsider. But if nothing has changed except how you're feeling, perhaps the invitation isn't to reopen the decision.

Perhaps it's to allow yourself to feel uncertain about a choice you've already made.

You don't have to feel confident about your decision every minute of every day. You don't have to eliminate every doubt. And you don't have to interpret every uncomfortable feeling as a sign that something has gone wrong. Sometimes you can simply say:

Yep, I'm feeling anxious about this. That makes sense. I made a thoughtful choice, and I don't know exactly how it's going to turn out.

And then get on with your life.

What if ease doesn't mean what we think it means?

When my client told me she wanted to make decisions with more ease, I understood what she meant. Who wouldn't want to spend less time overthinking, worrying, and second-guessing? But I've been wondering whether we sometimes misunderstand what ease actually looks like.

We imagine that making decisions with ease means feeling confident, calm, and certain. That we'll somehow reach a point where we know exactly what to do, make our choice, and never look back. But I'm not sure that's a realistic goal.

Some decisions are genuinely hard. They involve competing desires, meaningful trade-offs, and outcomes we can't predict. Sometimes making an aligned decision means disappointing someone we love. Sometimes it means giving up something good in pursuit of something that might be better. Sometimes it means accepting that there is no perfect option. And sometimes it means making a choice that feels scary, even when we know it's what we want.

Maybe ease isn't the absence of discomfort. Maybe ease comes from no longer being at war with the discomfort.

From allowing ourselves to take the time we need, without constantly criticizing ourselves for it. From recognizing when we've done enough thinking, without demanding absolute certainty. From making room for fear and doubt, without allowing them to run the show. And from accepting that being human means making choices without knowing exactly how the story will unfold.

A different way to approach your next decision

The next time you find yourself stuck in a decision, I'd invite you to pause and ask yourself three questions:

1. What do I actually need to move forward?

More information? More time? More support? Or a willingness to choose without certainty?

2. What am I making it mean that this feels uncomfortable?

Am I telling myself I'm indecisive, incapable, or doing something wrong because I haven't figured it out yet? Can I offer myself a little more compassion?

3. What would change if I stopped expecting this decision to feel easy?

Would I give myself permission to take more time?

Would I stop researching and make the choice?

Would I allow myself to feel anxious without immediately trying to fix it?

Would I finally let a decision I've already made be made?

There's no single right way to navigate every decision. But I think we can make the experience a whole lot less painful when we stop treating discomfort as evidence that something has gone wrong.

You don't need to become someone who never feels uncertain. You can become someone who knows how to be with herself when she does.

And that, to me, sounds like a much more meaningful kind of ease.

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