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 "I don't know what to do, Jess!"

Most coaching sessions start here, with decisions that feel like being stuck between a rock and a hard place: Fire the underperformer everyone loves? Risk damaging company culture in favor of hitting runway targets? Leave the prestigious role that's making you miserable? Hire externally and potentially alienate your team, or promote internally and take a bet on an unproven rising star?

We’re taught that we need more data, more frameworks, and more expert mentors. For much of your career, this external approach—distilling what you "should" do from what others have done—has worked.

But for the toughest calls, there is no universal "right" answer. That’s why my clients arrive exhausted, either from researching what they should do or from avoiding the decision entirely.

Somehow, these conversations almost always end with: "Actually, the choice is pretty obvious, isn't it?"

So, what's happening during that conversation? What's the secret alchemical ingredient that transmutes "🤷" into "💡?"

It’s Not Alchemy, It’s Archaeology

I recently worked with a senior leader facing a "should I stay or should I go" decision. She had amazing compensation, solid benefits, and tons of flexibility needed for family life.

Buuuut, she was miserable.   

Her boss resisted innovation, there was little hope for advancement, and little autonomy. All of which added up to a wholly unfulfilling work life. “But then again, the pay and flexibility are so good, isn’t it worth just sucking it up for another year or two?” 

As we navigated the maze-like “shoulds” and “what-ifs”, we hit bedrock: 

 "It's too many hours to be away from my family doing something that makes me miserable. It needs to be more meaningful work."

"I think you just answered your own question," I pointed out.

So, what happened? What was the alchemical ingredient? Afterall, I hadn’t given her any new information; I just helped her move the debris of “shoulds” out of the way so she could see her situation more clearly. 

Turns out, she didn’t need alchemy; she simply needed to excavate. 

As humans, we gravitate to formulas and frameworks, right answers and easy buttons. But in the middle of these rock-and-a-hard-place decisions, clarity isn’t handed to us in a convenient framework; it’s buried under layers of: 

• Fear of making the "wrong" choice

• Anxiety about what we can't control

• Grief for the option we'll have to let go

• Stories we've told ourselves about who we "should" be

This type of excavation can be uncomfortable, time-consuming, and messy. But the end result is usually paydirt.

How to Excavate The Answer

1. Get clear on what you're actually optimizing for

Not what you think you should optimize for. Not what would make your loved ones proud or impress your LinkedIn network. What matters to you, right now, in this specific season of your life?

My client initially framed their decision around compensation and career trajectory—the "sensible" factors. But as we talked, we discovered what they were really optimizing for: meaningful work that justified time away from young children. That removed much of the fog around their decision.

For another client—a CXO deciding whether to promote internally or hire externally for a VP role—the real question wasn't about the candidate's capabilities. It was about what kind of team culture he wanted to cultivate and how much risk he could absorb given everything else on his plate.

If you did last month's reflection and intention exercises, this is where it pays off. When you know what you're building toward, decisions stop feeling arbitrary and start feeling aligned.

2. Test-drive the outcomes

Simply knowing you're blocked doesn't unblock you. To cut through the mental gymnastics, it helps to bypass the conscious brain entirely. Here is how:

Flip a coin. 

Assign Choice A to heads and Choice B to tails. The data isn't in how it lands; it's in your reaction to the result.

As that coin is dancing in the air, pay attention to the split second where you find yourself rooting for one side over the other. If it lands on tails and you feel a flash of disappointment (or a wave of relief), you have your answer.

Don’t have a coin handy? Close your eyes and imagine you've made Choice A. Sit with it for 30 seconds. How does your body feel? Now imagine Choice B. Notice the difference in your heart rate or tension in your body.

Your body often recognizes a pattern or a truth before your conscious mind has finished processing all the variables. By simulating the outcome, you're treating your physical reaction as a high-speed data point that bypasses your internal filters, and leverages the same shortcut as when you “listen to your gut”.

3. List the factors—including the emotions

Make your pros and cons list. But don't sanitize it. Include the hidden information your test-drive exercises uncover, and the messy truths that are tough to look at: 

• "I'm scared of disappointing people."

• "I don't want to admit I made a mistake taking this job."

• "I'm worried I'm not good enough for what comes next."

Emotions aren't obstacles to good decision-making. They're data. That fear? That grief? That excitement? All information about what matters to you and what the real stakes are.

My client's list included not just the obvious professional factors, but also: "I'm worried I'll regret giving up financial security" and "I'm afraid of what it means if I admit this prestigious role isn't right for me." 

Once those were named, they could be weighed appropriately rather than lurking as nebulous anxieties.

4. Acknowledge what you're losing

I once had a boss who’d describe choosing one priority over another this way: 

“Real priorities should be painful. It’s like deciding whether to cut off your right arm or left leg. Both seem vital. But you are only allowed to keep one to move forward.“

Gruesome metaphor? Absolutely. But it forces you to acknowledge the reality of decision-making: 

Even when you make the "right" choice, you lose something—and it likely hurts.

• In deciding to leave the job that's making you miserable, you'll miss the financial cushion and the flexibility. 

• In firing the problematic direct report, you'll miss the bandwidth they provided when you didn't have to absorb their workload. 

• When you leave the relationship that's run its course, you still miss the times when it was good.

Psychologist Lori Gottlieb observes: "Change and loss travel together." You can't have one without the other. And if you don't acknowledge the loss, it'll sabotage your commitment to the change.

So give yourself permission to grieve. You don’t have to wallow; just acknowledge it. "Yes, I'm going to miss X. And I'm still choosing Y because it's more aligned with what I need right now."

5. Commit and manage the outcomes

The addendum to the analogy above is this: Choose one, tourniquet the other, and keep going.

Once you've made the call, your job shifts from deciding to executing. Set aside the second-guessing. Stop fantasizing about the discarded option. Put your energy into making your choice work.

This doesn't mean blind optimism. It means: "I've made the bed, and I'm going to do everything I can to make lying in it comfortable." Adjust as you go. Learn from what unfolds. But keep moving forward.

Start Small, Build the Muscle

Decision-making is unavoidable, doubly so when you’re leading an organization in this day and age. If you’re not facing a massive decision right now, I’m willing to bet it won’t be long before you have to.

Take the time now to practice with lower-stakes choices:

• Which clearly qualified candidate to hire for an IC role

• Whether to attend that conference

• How to structure your week

The skill of trusting your own judgment builds through repetition. Each time you make a call, honor it, and manage the outcome, you strengthen that muscle.

If you are facing a rock-and-a-hard-place decision, time to stop looking to others for the answer. You already know what you need to do. You might not like it. You might be scared of it. You might be grieving what you'll lose by doing it.

But you know.

Keep reading, keep leading,

Jess.

P.S. If The Left-Hand Column has resonated with you, consider supporting my work by clicking on one of the ads below. It's a small action that has a big impact!

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