You did everything right. So what went wrong? [better work #39]


better work issue #39

Imagine you're out with friends celebrating a major milestone. You sip a few cocktails and feel warm and fuzzy. Closing time comes.

You realize you drove there. Rather than call a taxi and deal with picking up your car tomorrow morning, you choose to drive home. You get in your car, press its ignition button, and pull out of the parking lot.

You get home without getting into a wreck - a good outcome.

Does that mean drunk driving was a good call? Nope.

You can make a bad decision (drinking and driving) and end up with a good result (making it home safely). It's not because you're an excellent driver while intoxicated. It’s not because you’re more clever than people who did get DUIs or an even worse result.

The outcome was good because you got lucky.


The luck factor

It’s easy to judge decisions by their end results, but results don’t happen in a vacuum. Good or bad, results are contaminated by chance. That’s why a good decision - one that was thoroughly researched and practically perfect in every way - can end badly. That’s why the opposite holds true too.

When you’re staring down the barrel of a bad result, it’s hard not to kick yourself a little.

I should have known better!” But you didn’t.
Why didn’t I see this coming?” Because you’re not psychic. (...Are you? 🧙🏻‍♀️)

It’d be nice if we weren’t working with a dozen variables all the time, but we are. Shifting how we internalize “bad results” helps us see our life more clearly. Because sometimes a good decision, like getting married, gets us a bad result, like getting divorced.

Let's continue with that divorce example for a moment. It actually happened to an acquaintance of mine. Years ago, I met a woman named Michelle. She was in her forties and truly fabulous.

Michelle was the embodiment of sunshine. I couldn’t imagine why a single person wouldn’t adore her. When she casually mentioned her divorce, I immediately assumed her ex-husband, the bastard!, fucked up.

I was wrong.

Michelle shared that they got married straight out of graduate school. They lived a pretty peaceful life for 10 years. One day, they realized they were closer to siblings than partners.😬

They had no kids and no drama in their divorce (a rarity).
"He's still my best friend," she said with a bright smile.

A divorce sans drama is still a divorce, arguably a “bad” result. No one gets married believing they’re divorce-bound. But it happens. So is marriage a “bad” decision if it comes to an end?

Not always. Michelle is living proof.


The fear you're actually feeling

Think about all the bad decisions you've made. Big and small. Now go down your list and ask yourself: Why do I view that as a bad decision?

Oftentimes we judge our decisions based on the consequences they have on us.

  • Bad result = bad decision.
  • Good result = good decision.

It’s important to look at your life holistically. You make thousands of choices per day. The closer you look, the more you’ll see this clearly: there’s no one equation that leads to good results or bad ones.

Still, when you get bad results you think, “I’m no good.”

It's simpler to believe we must have made a mistake. The monkey on our back tells us we didn't plan enough, we didn't consider enough angles, we didn't use enough discernment before moving forward.

That’s not always the case, especially when high-performers are involved.

High-performers are terrified of making the wrong decision. We will stay in miserable jobs, relationships, and situations until we feel capital-C Certain about leaving them. Even after we do, we will second-guess ourselves no matter the outcome - what if there was an even better option we missed out on??

Many clients of mine come to me wanting to change their lives but admit they’re scared to make the wrong decision. The first thing I tell them is they’re misnaming their fear.

You’re not afraid of making a bad decision.
You’re afraid of getting a bad result.

Sitting in one spot for too long and mulling options over - that's a decision too, and it is not a neutral one either.

Then we lower the stakes. It's highly unlikely something horrendously bad is going to happen. The odds are incredibly low that one decision will blow your life to pieces.

So low, that you could bet nothing will happen and win almost every time. Like this guy, who made two million dollars after betting “nothing will happen” to every non-sports event.

I'm not going to tell you to "just stop" being afraid of making the wrong decision because that's more useless suggestion than solution.

Instead, practice making decisions with uncertainty. The actual result doesn't really matter - it's how you respond to that result that matters in the end.

This can be really simple. Walk into a new restaurant without checking the reviews because you simply liked the vibe. Say yes to a coffee chat with someone outside your field. Pitch a half-baked idea in a low-stakes team meeting without prepping yourself for hours.

Regardless of the results, I promise you will not die.


May the odds be in your favor

The skill of making decisions based on unknowns takes a combination of research, creativity, courage, and luck. Luck is the most random factor of all our decisions.

It’s the one we don't like thinking about because we can't control it, though it's amusing how we try.

Fingers and toes crossed.

We don't like to believe that no matter what we do, the randomness of luck can tip the scale. That's why you’re already ahead when you confront it.

If you want to get better at making decisions amidst uncertainty (a skill that's going to be highly coveted in the future - it’s one AI can’t do), you first need to reframe how you view good vs. bad decisions, especially the latter.

Next time you receive a bad result and catch yourself saying, "Ugh, I should have known better."

Follow that with, "I did the best I could with the information I had at the time."

You have to forgive yourself when you get bad results.

Forgiveness is what grants us permission to try again. This is how we learn to trust ourselves with future decisions.

If you want to strength train your uncertainty muscle, we have a program for you. Forward on Purpose is having its inaugural cohort this September.

Together, we are working toward clarity on what we want and the conviction to move toward it without waiting for perfect conditions.

Fear of the unknown? We don’t know her. You can apply to join us today.

Faith in yourself is easiest to build with a group of people rallying behind you. That's the secret behind those who seem to always get 'good' results. They don't avoid the bad results - instead, they surround themselves with good people and trust themselves enough to know how to make things good again.


Susan Lee

Founder and Career Coach, Hey Ms. Lee, LLC

Here are 3 ways I can help you:

  1. There is a framework on how to live beyond survival and you'll find it inside Forward on Purpose this September. Book a no-strings call with me to see if this program is right for you: apply here (4 spots left).
  2. Struggling to make a decision on something and need an unbiased perspective? 🧠 Rent-My-Brain sessions are now available! Use the code BETTER10 for 10% off your first session (must book before 8/31/2026).
  3. If you're ready to make an unconventional career pivot and want an expert in your corner, learn more about 1:1 coaching with me.

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Susan Lee

better work is a personal development newsletter that helps high-performing women find out who they really are, what they actually want, and how to find work that finally aligns with their values - without the self-help bullshit.

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