How to make strategic decisions as a business owner

May 18

Every business owner has been in the same place - they have a decision they need to make and another day has gone by of convincing yourself “oh, I’ll think about it after I get this email drafted” or “I need to do a bit more research.” When you’re the boss, the decisions almost always fall to you and it can be draining over time.

And it’s not just the big ones: everything from your CRM software, how to handle a situation with a client or bringing on a new contractor can weigh on your brain.

After now 5+ years in small business and talking with a lot of fellow business owners, I’ve noticed that the problem usually isn’t needing more information (even though we like to convince ourselves that another Claude search will clarify everything. Most business owners who find themselves stuck in analysis paralysis aren't indecisive people. They're hitting mental blocks that make it feel impossible to decide and then beating themselves up for not having decided.

That’s why I think it’s so important that we real talk about decision making as a business owner, what actually makes it hard and dive into some ways to get unstuck.

Prefer to watch? Here's the video!

Embed Block

Enter a valid embed URL or code.

Why you're stuck on business decisions (and how to get unstuck)

Not all decisions work the same way

The simplest reason I think a lot of business owners get stuck because they think all the decisions need to be approached the same way. In fact, there are different types of decisions and we need to understand what we’re deciding on in order to be able to move forward.

Some decisions are comparisons: you know what you're choosing between and the question is just which option is the better move. Think like choosing between Diet Coke and Coke Zero (Diet Coke is the correct answer, btw). Or between softwares to use for your CRM.

Other decisions are more open ended - they are trying to address a problem with practically infinite potential solutions. Needing more clients is a good example. There are a hundred different ways to solve for that, which means "just picking one" isn't really a decision-making problem, it's a strategy problem. These decisions are about trying to find the solution that will address your problem. These feel more complicated than the first category because you’re not just evaluating features or functions but trying to come to an educated conclusion of whether what you choose will be effective at what you want it to solve.

And then there's a third category: decisions that aren't just about whether something will work, but about how it will affect bigger things like your lifestyle, your capacity, and what your business actually looks like to run day to day. These decisions are even more complicated than the open-ended decisions because the question isn’t about whether something will work but whether it will work for you.

When you’re trying to decide if how to get more clients, you can use evidence and experience from other people to help shore up your confidence in whether something will work. When you’re deciding on a path in terms of whether or not you’ll like it, enjoy it or be good at it, the only person you have to look to is yourself.

Most business owners get stuck not because they're indecisive or missing information, but because they're in that second or third category and trying to apply the logic of the first.

The analysis paralysis comes from trying to find an objectively right answer in a situation where there is no objective right.

Getting clear on what type of decision you're actually making is the first move. It may not solve the whole thing, but it usually changes what you realize you need in order to move forward.

Four ways to work through a practical decision

If you're dealing with a concrete choice, like picking a software tool, deciding whether to invest in a coach or consultant, comparing two vendors, here are four approaches that tend to make the path forward clearer.

Narrow it to two choices. Research has shown that the more options you have, the harder it is to decide. So narrow the field first. That can mean action versus inaction (hire the consultant or don't), or it can mean picking the two strongest candidates and comparing just those. Fewer options, easier decision.

Separate must-haves from nice-to-haves. This is especially useful when you're choosing a software tool. There's usually one feature, or a small set of features, where if they're missing, the decision is a failure regardless of everything else the tool does well. Figuring out your must-have criteria upfront lets you cut through the marketing noise and evaluate what actually matters. (If you're currently in the middle of a software decision, this video goes deep on how to work through it.)

Look at your risk profile. The concept of asymmetric risk is useful here. A good bet is one where the potential reward is large relative to the potential risk. Spend $10,000 to potentially make $100,000? That's asymmetric in your favor, and often worth it. Spend $10,000 to make $10,000? Less compelling. The more important check is the flip side: if the upside is great but the potential downside involves losing client trust, damaging your reputation, or taking on financial exposure that dwarfs any possible return, then that should dissuade you from the decision. Taking a few minutes to force yourself to think about the risk reward balance can help cut through some noise.

Make it numerical. One way to get unstuck is to put some numbers to the decision. Our favorite way to do this is to calculate ROI. It forces you to put actual numbers on the table, not just in dollars but in time, and to estimate a realistic potential return. (Here's the video where I walk through how to calculate it.) Have you actually mapped out the costs of the decision in money and your time (or your team’s time)? Have you actually estimated how much money you think it will make you or time it will save you? And what’s the alternative in time and money? Putting things in real numbers can force you to get honest about your assumptions and think a level deeper.

But beyond the math, there's something about seeing the two numbers side by side that can work like flipping a coin: you often immediately recognize what you were already leaning toward. Sometimes the exercise is just the push that gets you across the line!

Why complex decisions feel impossible

Some decisions don't fit neatly into a side-by-side comparison. They're layered, interconnected, with a reasonable argument on both sides. What should you do to close more clients? Should you launch the new offer? These decisions are not just about picking the better of the two options, because what makes one option better than the other is more complex. Here are three reasons why these types of decisions are easy to get stuck on:

You're not clear on the problem you're trying to solve. This comes up often in client conversations at Exhale. Someone wants to bring on more business but has no idea where their hours are actually going. Or they want more visibility but can't pin down what's holding them back. When the cause is unclear, picking a solution feels like throwing a dart at a dartboard: you’re trying something and hoping it does what you want. If this is where you're stuck, keep evaluating solutions isn't the answer. Stepping back to diagnose the root cause is. Once you know what's actually driving the problem, the decision on how to solve it usually becomes a lot more obvious. (We almost always work through this with our clients so if you’d like some support here, reach out!)

You're not clear on the trade-offs. Say you want to build a digital products business, but you haven't fully thought through what fulfilling those products looks like, what it means for staffing, or how you'd handle customer issues. When choosing a strategy comes with a whole host of unknowns that might pop up as a result, of course it feels intimidating! Mapping out the second-order effects, what's downstream from this decision, tends to clear things up. Write down your potential next steps and then jot down any potential impacts you think that might have on your business (your time allocation, the flow of traffic through your website, software you’d need, jot down anything you can think of!) Once you have a clearer picture of all the ramifications of a decision, you’re likely to start to see which ones you're willing to accept, which ones you might be able to mediate the risk of and which after-effects you aren’t willing to even risk.

But the third reason why we see many business owners get stuck on a decision is…

You don't actually know what you want. This is the root problem underneath both of the above. Not "I want a successful business and to make money." That's the surface. There are deeper visions you have for your life, for your business, for what you want your days to look like but if you aren’t clear about them than evaluating solutions or tradeoffs gets very complicated because you’re not just choosing a next step, it feels like you’re choosing a life path.

For business owners, some deeper questions that many haven’t yet answered: do you want to be publicly known or stay relatively private? Do you want to manage a team, or stay solo? Are you building toward some big external outcome like a sale or a merger, or would you be happy running your business until you decide to close it down (many people call this a lifestyle business)?

If you can’t answer these questions with conviction, of course it’s hard to make big strategic decisions for your business because you’re not sure if you want to commit yourself to a certain long term path with this next decision. Once you start to get clear for yourself on the longer term vision, you start cutting large branches off the decision tree and ass we discussed above, when there are fewer options, decisions feel easier to make.

The phrase I use when I'm feeling stuck on a decision

Even after working through all of the above, decisions can still be hard. As a recovering perfectionist, I (Sam, Exhale Founder!) can spiral into real anxiety trying to map out every possible scenario, every potential failure, every downstream consequence. What I realized was that I was putting an impossible job on today me: account for every problem that might come up over the next year (or more) before taking the first step.

The phrase that I turn to regularly: trust your future self.

When I'm sitting with a big decision, I can't predict every scenario, even if I try to convince myself I can. I can't know what will change or what the situation will look like six months from now. Trying to think through all of that isn't preparation. It's just pressure, and I'm putting all of it on today me.

So instead, I make the best decision I can with what I know right now. And then I trust that future me can handle what comes next.

If the decision turns out to be wrong, future me will find a solution. If something starts going sideways, future me will see it and make adjustments. If it goes really wrong, future me will cut losses early. That's not a failure of the original decision. It's good business.

Reminding myself of that doesn't mean making decisions carelessly. It means releasing the expectation that today you has to be omniscient. Your job is to make the best call you can with the information in front of you. Trusting that future you is capable of handling what comes next takes a surprising amount of pressure off the decision you're trying to make right now.

If you're sitting on a decision that's been taking up mental space, start here: figure out what type of decision it actually is. That one step can get you moving. Still stuck? Try drafting out must haves vs. nice to haves or make it numerical. Still feeling stuck after that? Consider whether there might be something deeper about your own clarity that’s making the decision hard. And if you’ve done all the background work but still feel paralyzed? Can you put the trust in future you and just make the best decision you can with the information you have right now so you can get moving?

Frequently asked questions

How do I figure out what type of business decision I'm making?

Start by asking whether there's a clear right answer at all. If you're choosing between two specific options and the question is really about which one performs better, that's a practical decision and the tactics above apply directly. If the problem you're trying to solve has practically infinite potential solutions, or if the decision involves bigger questions about your lifestyle, team, or business model, you're in more complex territory. In that case, before evaluating options, try to clarify what the actual problem is, what trade-offs you're willing to make, and what you actually want from your business at a deeper level. The type of decision shapes what approach will actually help you move through it.

What should I do when I've analyzed a decision from every angle and still can't commit?

Try making it numerical first. Calculate the ROI of each option, including your time as a cost, and put it on paper. The act of forcing numbers onto a decision often cuts through the fog faster than more analysis will. If you've done that and you're still stuck, the issue usually isn't the decision itself. It's the pressure you're putting on yourself to get it exactly right. That's where trusting your future self comes in: your job right now is to make the best call with what you know today, not to guarantee that nothing will ever go wrong. Future you is capable of adjusting if something doesn't work out the way you hoped.

Is it okay to change your mind after making a business decision?

Yes. One of the things that makes decisions feel so heavy is the belief that they're permanent, and most aren't. Changing direction based on new information isn't indecision. It's how good businesses operate. The goal of any decision is to make the best call you can with what you have at the time. If the situation changes, or if the decision clearly isn't working, adjusting is what you're supposed to do. Building in a review point after major decisions, rather than treating them as fully fixed, can also make it easier to commit in the first place.

How do I calculate the ROI of a business decision?

ROI for a business decision means estimating total cost (including your time converted to a dollar value, not just direct expenses) and comparing it to a realistic potential return. The calculation: potential return minus total cost, divided by total cost, times 100. But the math is less important than the exercise itself. Putting both sides of the decision in writing forces you to be specific about what you're actually risking and what you're realistically expecting to get back. That specificity tends to make the right direction much clearer. This video walks through how to apply it in practice.

When should I get outside help to work through a business decision?

When you can't get clear on the root cause of the problem you're trying to solve, or when you've been circling the same decision without making progress, outside perspective is usually worth it. A fresh set of eyes from someone who understands your business model and isn't inside the emotional weight of the decision can surface what you've been too close to see. At Exhale, working through strategic decisions is one of the first things we do with new clients — diagnosing what's actually going on before deciding what to do about it.