How to Make a Big Decision Without Regret

You've got a big decision to make. You've thought it through. You're pretty sure you know the answer.

Then it's 2 a.m., you're staring at the ceiling, and a little voice pipes up: "What if this is a huge mistake?"

And just like that, you're back at square one.

After 30 years on Wall Street and investment management making big investment decisions, I've learned that even good decisions can turn out badly. Believe me, I’ve made my share of doozies.

So in the next few minutes, I'll show you how to make a big decision without letting fear drive your decisions, how to shrink the risk, and how to quit second-guessing yourself afterward.

I'll also tell you about a client of mine who used all this to change her life. And there's one question near the end that'll change how you look at every decision you make. Hang around for that one.

Here's something I've noticed about people who get stuck on big decisions.

A lot of them are really successful. They've spent years making tough calls at work. They've managed people, put out fires, and taken on way more than their fair share.

Then it's their own life on the line, and they freeze. And they can't figure out why. 

Well, there's a good reason. We'll get to it in a second.

At work, you've got a goal. You've got facts. You can line up your options and pick one. It's pretty clean.

Your own life is a different animal. Now you're not thinking about what you could win. You're thinking about what you could lose.

You worked hard to get where you are. You built a life that's safe and familiar. Maybe parts of it make you crazy, but hey, at least you know what to expect.

And that's where the trouble starts.

Your brain starts playing a little movie of everything that could go wrong. And it never plays the happy ending. Nope. It skips right to the disaster scene.

There you are, six months from now, thinking, "What on earth was I thinking?"

Here's the weird part. None of that has happened. You haven't even made the decision yet. And you're already feeling lousy about how it turned out.

There's actually a name for this. It's called anticipated regret. That's a fancy way of saying you're scared you'll make a choice and wish you hadn't.

And it gets better. You can feel that way about either choice.

Say you're thinking about leaving your job. If you leave and it doesn't work out, you'll kick yourself for not staying. But if you stay, you might look back in five years and wish you'd had the guts to go.

So now you're scared to leave, and you're scared to stay. Quite the pickle.

So what do you do? Nothing.

You just keep thinking about it, because thinking feels safer than choosing. It also feels like work, which is a nice touch.

But here's the thing. Not deciding is still deciding. You're choosing to keep everything exactly as it is. And that choice has a price tag, too.

You might be giving up time you'll never get back. You might be passing on something that would make your life a whole lot better.

Now, I'm not saying you always have to change something. Sometimes staying put is the smart move. I just want you to pick it because you thought it through, not because you were too scared to pick anything else.

So here's a question for you. If there's a big decision you've been putting off, what happens if you do nothing? What does your life look like a year from now? Is that really what you want?

Hold onto that, because I'll circle back to it.

First, I want to deal with the biggest reason this is so scary. It's the belief that if things go wrong, it means you made a bad choice.

That's not always true. And I know that because of how I spent my career.

If 30 years of investing taught me anything, it's that you can make a good decision and still lose money.

Picture it. You spend weeks digging into a company. You study the business. You see how much money it makes. You work out what you think it's worth. You do your homework.

Then you buy the stock. And six months later, it's down.

Was that a bad decision? Not necessarily.

Maybe something happened that nobody saw coming. The economy shifted. The company hit a problem that wasn't there when you bought it. You made the best call you could with what you knew at the time. That's all anyone can do.

Now flip it. Say your neighbor tells you about a "sure thing." You don't know a thing about the company. You never looked at the books. You just buy it.

And the stock doubles.

Wonderful. Does that make you a great investor?

Nope. It makes you lucky. And if you keep investing like that, your luck's gonna run out, probably right around the time you stop paying attention.

Here's my point. A good result doesn't always mean you made a good decision. A bad result doesn't always mean you made a bad one. Those are two different things.

And that goes for your life, not just your money.

Say you've been miserable at work for years. You've saved up. You've figured out what you'd like to do next. You've looked at the risks. So you quit and start your own business.

A year later the economy tanks and things get rough.

Does that prove you were wrong? No. You ran into something you couldn't have seen coming.

Now, if you quit with no savings, no plan, and no clue whether anyone wants what you're selling? Different story. That's not a risk you thought through. That's crossing your fingers and hoping.

Here's the part I really want you to get. You can't control what happens after you decide. But you can control how you decide.

You can do your homework. You can think about what might go wrong and how much risk you can stomach. You can make sure the choice fits the life you actually want.

Then you make the best call you can with what you know. Because if you wait until you know how everything turns out, you'll be waiting a very long time.

Trust me on this one. Even the people who get paid a fortune to predict the future are wrong all the time. They just explain it in longer sentences.

Now let me show you what this looks like in real life, because I worked with a woman who was stuck in exactly this spot.

Her name was Sarah. Big career. She'd worked her way up to director, with a ton of people reporting to her and a mountain of responsibility. From the outside, she was crushing it.

There was just one small problem. She was miserable. Burned out. She wasn't happy with the work anymore, and she was starting to wonder if she wanted to do this for the rest of her career.

What she wanted was to take everything she'd learned over the years and start her own business. She loved the idea of being her own boss. She wanted to do work she actually enjoyed and have a say in how she spent her time. And she wanted to live wherever she felt like living. Her job had her tied to one place, and she was tired of building her whole life around her company's needs.

So starting a business made total sense. At least until she started thinking about everything that could go wrong.

What if it failed? She had a good job and a good paycheck. Why give that up for something that might not work?

Then she started worrying about what people would think. What would her colleagues say if she walked away? Would her friends think she'd lost her marbles?

And then there was her boyfriend.

He wasn't exactly cheering her on. She knew a new business would eat up a lot of time, especially at first. She was already stretched thin, and she worried it'd leave even less time for them. Then another question crept in. If he didn't support something that meant this much to her, did she even want to stay with him?

So now Sarah wasn't just deciding whether to leave her job. She was trying to sort out her career, her future business, and her love life, all at once. And the more she poked at one, the more it tugged on the others.

You can see how this spirals fast. She felt like she had to solve her entire life before she could make one single move.

That's where she was when we started working together.

Now, I didn't tell Sarah to quit. I didn't tell her to start a business. And I definitely wasn't going to tell her what to do about her boyfriend. That's not my job as a coach. My job is to help you get clear enough to make your own call, because you're the one who has to live with it.

So we worked through my seven-phase C.L.A.R.I.T.Y. framework. It's a step-by-step way to handle big decisions without drowning in fear and confusion.

First thing we did was slow way down. When you're worried about a big decision, your brain bounces from one problem to the next. You haven't finished the first worry, and you're already stressing about year five. It's exhausting.

So we got clear on what Sarah was actually trying to decide. Sounds simple, right? But you'd be amazed how many people spend weeks agonizing over a decision without ever saying out loud what the decision is.

With Sarah, it wasn't one decision. It was several. Once we pulled them apart, we could look at each one without dragging the others along.

Take the business. Sarah was afraid it might fail. Well, she was right. It might. Starting a business is risky, and I wasn't going to sit there and tell her it'd all work out if she just wanted it badly enough. I looked at too many companies for too many years to believe that fairy tale.

But risky doesn't mean don't do it. It means understand the risk.

So we sorted out what she could control and what she couldn't. She couldn't make people buy. She couldn't control the economy. And she couldn't know how big the business would get.

But she could decide how much money she was willing to put on the line. She could find ways to protect herself if things went sideways. She could decide what needed to be in place before she took the next step.

Now that she could work with. Instead of sitting there worrying the business might fail, she started figuring out how to lower the odds. And that changed everything.

Then we looked at something bigger. What did Sarah actually want out of her life?

She'd spent years climbing. She'd earned that director title, and that's a big deal. But at some point you have to ask yourself if the thing you worked so hard for is still something you want.

Sometimes it isn't. Sometimes your life changes, but you keep chasing the same goal because, well, you've been chasing it forever. And letting go is hard. You've put in so much time that walking away feels like tossing it all in the trash.

But Sarah wasn't tossing her experience. She was planning to use it a different way.

And as we dug into what mattered most, she realized freedom was way higher on her list than she'd thought. She wanted to enjoy her work again. She wanted control over her time. She wanted to choose where she lived. Those things mattered more than hanging onto a title that no longer made her happy.

That was a big shift. Now she wasn't only asking what she'd lose by leaving. She was asking what she could gain.

Then we got to the relationship. And this was a tough one.

Her boyfriend wasn't excited about her plans, and she was starting to wonder if he was the right guy. So we looked at that too. What did she want from a partner? How much did it matter to have someone in her corner? And what could she actually control?

Well, she could be honest with him about what she wanted. She could explain why this mattered so much. And she could decide what she needed in a partner.

But she couldn't make him feel a certain way. She couldn't force him to be supportive. That part was up to him.

And this was a big aha for Sarah. She'd spent so much time worrying about how everyone else would react that she'd almost forgotten she got a vote in her own life.

Once we'd worked through the decisions, sized up the risks, and figured out what mattered to her, Sarah could finally see a way forward. Not because the risks had vanished. Not because she suddenly knew the future. But because she knew what she wanted and what she could do about it.

And she made her decision. She decided to start her own business. She was going to use her experience to build something of her own, something that gave her freedom to do work she loved and live where she wanted.

But here's the part of her story I find most interesting.

Remember the boyfriend? The one who wasn't thrilled?

Something happened once Sarah made her decision. When she took that step and showed him how serious she was, his attitude changed. He saw how much this meant to her. And instead of pulling away, he gained a whole lot of respect for what she was doing. He ended up supporting her way more than she ever expected.

Now think about that. Before she decided, Sarah spent ages worrying about how he'd react. And she had good reason to. But she couldn't know until she actually made her choice. And his response turned out better than she'd imagined.

Now, I'm not saying everyone in your life will throw you a parade when you make a big decision. That'd be lovely. I wouldn't count on it, though.

The point is that Sarah couldn't control his reaction. She could control how she made her own decision. And once she got clear on what mattered, she took the next step.

She didn't need to know how it'd all turn out. She needed to understand the risks, figure out what was important to her, and make a choice she could stand behind.

And here's the part I think is even more valuable. She didn't just solve one decision. She learned a method she can use again. Because life isn't going to stop handing you tough choices just because you handled this one. I wish it would. But I wouldn't plan on it.

Now, if you're hearing Sarah's story and thinking, "Yep, that's me," I've got something for you.

When I coach people through big decisions, I almost never find that they need more information. They need less noise. All those worries and everybody else's opinions get so loud you can't hear what you actually want. I call that decision noise.

So I put together a free Decision Clarity Audit to help you figure out what's getting in the way. The link's in the description below.

Okay, now let's talk about what happens after you make your choice. Because making the decision is one thing. Not driving yourself nuts afterward is another.

Say you've finally decided. You thought it through. You looked at the risks. You know why you're doing it. Great.

Then a few days later you wake up and think, "Hang on. Did I do the right thing?"

And boom, you're right back to worrying. You start thinking about the road you didn't take. You wonder if you should've waited. Before long, you're replaying the whole thing like it's game film.

Sound familiar?

Here's what I need you to know. Changing your mind because you learned something new is not the same as changing your mind because you're scared.

Say you started a business, and a few months in, nobody's buying. That's real information. Maybe you tweak what you're offering. Maybe you find better ways to reach customers. Maybe you decide it's not gonna work. That's not a failure. That's learning.

But say nothing's changed. You just wake up one morning feeling jittery and wondering if you blew it. Well, feeling nervous doesn't mean you made the wrong call. It might just mean you're doing something new. And new stuff feels weird.

People treat every uncomfortable feeling like a fire alarm. Sometimes it is. But sometimes you're just scared because you don't know what happens next. And those are very different things.

That's why the last phase of my C.L.A.R.I.T.Y. framework is called Yield the Learning. It's about looking back at what happened after you decided, and learning from it. What worked? What didn't? What did you know when you made the choice, and what do you know now? Then you use that to make better calls down the road.

You don't need to spend the next five years beating yourself up because it didn't go exactly like you pictured. Trust me, that gets you nowhere.

In my years in the investment business, plenty of my decisions didn't pan out. Comes with the territory. And if I'd decided I was a total idiot every time something went down, I'd have had a very short career.

Now, sure, sometimes I really did screw up. Maybe I missed something big, or leaned too hard on one piece of information. When that happened, I had to figure out what I did wrong so I wouldn't do it again. But that's a long way from assuming every bad result means a bad decision.

Same goes for your life. You can make a thoughtful choice and still end up disappointed. You can take a shot and watch it miss. That doesn't mean you shouldn't have tried. It means you've got something to learn.

And one more thing. Making a decision doesn't mean you're stuck with it forever. Some decisions are hard to undo. Others you can change. Knowing which is which is one of the best ways to take the edge off the fear.

Thinking about a business? You might be able to test the idea before you quit your job. Thinking about moving? Maybe spend a few weeks in the new place first. Kick the tires.

The point isn't that every decision can be made safe. It can't. The point is you can often lower the risk before you make the big move. And when you do, the whole thing gets a lot less scary.

Okay. Earlier I promised you a question. This is the one.

Instead of asking yourself, "How do I know I won't regret this?" ask this:

"With what I know right now, could I still feel good about this choice, even if things don't work out?"

Totally different question. Because now you're not trying to predict the future, which, as we've established, even the pros are bad at. You're asking whether this choice makes sense based on what you know today.

Have you thought about the risks? Do you know why this matters to you? Have you done what you reasonably can to give yourself a shot at success?

If you have, you might be ready. Even if you're still a little nervous. And that's okay. You don't have to feel 100 percent sure to take the next step.

So here's what I want you to walk away with.

When you've got a big decision to make, the goal isn't to find a choice with zero risk. There usually isn't one. And the goal isn't to make sure you never feel disappointed, because sometimes you will.

The goal is to make a choice you can stand behind. You want to know you thought it through, you looked at what could go wrong, and the decision fits the life you want to build.

That's what Sarah figured out. She couldn't know if the business would work. She couldn't know how her boyfriend would react. But she could get clear on what mattered to her and decide what to do next. And once she did, she moved.

That's what I want for you, too.

Because you can burn a big chunk of your life waiting to feel completely sure. And with the decisions that matter most, you're probably never gonna feel completely sure. There'll always be something you don't know. There'll always be a chance it doesn't go your way.

But that doesn't mean you have to stay stuck. You don't need to know how everything turns out. You need to know how to make a good decision with what you know today.

And if it doesn't work out? You learn. You adjust. You keep going.

Because the real goal isn't to become someone who never makes a mistake. It's to become someone who can make a call, trust yourself enough to act, and handle whatever comes next.

And that's a skill you get to keep for life.

Now, if you're still chewing on the same decision over and over, you might be stuck in analysis paralysis. That's when you keep thinking and thinking, but you're not getting any closer to an answer. And the annoying part is it feels productive.

I've got another video, "Stuck in Analysis Paralysis? Do This Now," that explains why this happens and how to get out of it. I'll put it right here on the screen.

Watch that one next.

YOUTUBE DESCRIPTION 

How do you make a big decision without regret? If you're afraid of making the wrong choice, stuck overthinking, or second-guessing yourself, learn how to make hard decisions with confidence—even when you can't predict the outcome.

After 30 years making high-stakes investment decisions, I've learned something surprising: You can make a good decision and still get a bad outcome.

In this episode, I'll show you how to stop fearing the wrong decision, manage risk, and make choices you can stand behind. I'll also share how one of my coaching clients used my seven-phase C.L.A.R.I.T.Y. framework to make a life-changing career decision.

What You'll Learn

• Why fear of regret keeps you stuck in indecision
• How to tell a good decision from a bad outcome
• How to reduce risk when making big life decisions
• How to stop second-guessing yourself after deciding

FREE Decision Clarity Audit: Discover what's keeping you stuck and what's getting in the way of making a clear decision.

👉https://www.gofreecrest.com/surveys/1UX1jcYts7iM2Xwp7aVr1yFt 

Timestamps

• 00:00 – What if you make the wrong decision?
• 00:30 – Why fear of regret keeps you stuck
• 04:45 – Good decisions can have bad outcomes
• 08:15 – Sarah's story: A career and life crossroads
• 14:45 – Free Decision Clarity Audit
• 15:20 – How to stop second-guessing yourself
• 19:00 – Making decisions you can stand behind
• 20:30 – What to watch next

👉 Watch Next: Stuck in Analysis Paralysis? Do This Now.
https://youtu.be/VFvPCFhlWaU?si=_YVszZqxInncA406 

#DecisionMaking #FearOfRegret #DecisionClarity