How to Make Big Career Decisions Without Fear: The 4-Part Risk Framework

You’ve been thinking about asking for that promotion for three months.

Or finally having the conversation with your boss about switching teams.

Or starting that side business you’ve been researching on weekends.

But every time you get close to pulling the trigger, you freeze.

“It’s too risky,” you tell yourself. “What if it backfires?”

I get it.

I spent 18 months agonizing over whether to leave Google. It felt like such a massive risk.

Giving up the salary, the security, the prestige of being a “Google executive.” Everyone thought I was crazy to even consider it.

But then I did something that changed my mind:

I made a 4-part spreadsheet.

And what I discovered shocked me.

The Problem

Big decisions feel scarier than they actually are because we think about risk as one giant, overwhelming thing.

“Should I leave my job?” feels terrifying. “Should I ask for a promotion?” feels impossible. “Should I start that side business?” feels uncertain.

But here’s what’s interesting: Research shows we’re worried about the wrong risk.

Dan Pink’s World Regret Survey found that people overwhelmingly regret the chances they didn’t take.

Neal Roese’s research on counterfactual thinking backs this up: the things we didn’t do haunt us more over the long run than the mistakes we made while trying.

So while you’re asking “What if this backfires?” the real question should be: “What if I don’t try and spend the next decade wondering ‘what if’?”

And when you break it down, most “big risks” aren’t as risky as they feel.

The Big Small Thing

Before you make any big decision, break down the risk into 4 categories. Then rank on a scale of 1 – 3.

1 = low risk

2 = medium risk

3 = high risk

1. Physical Risk

Will this affect your health, sleep, or physical wellbeing?

For leaving Google: I gave this a 1 (low risk).

Staying was actually worse for my body.

I had hip pain from stress. My eye was constantly twitching and my hair was thinning. I was up between 2-5 AM most nights with lowercase-a anxiety. I was essentially working five full-time jobs — my core role, running Own Your Career, handling outside speaking requests, being a wife, and being a mom.

Leaving would make me healthier, not sicker.

2. Cognitive Risk

Will this create mental stress, decision fatigue, or cognitive drain?

For leaving Google: I gave this a 1 (low risk).

I knew I’d learn more and grow faster as an entrepreneur.

At Google, I was doing incremental learning — a little bit each day. But starting my own business would be step-function learning. The kind that gives you butterflies in your stomach because you’re not sure how to handle a particular business decision.

I actually get excited by emails that challenge me now. That didn’t happen in my last few years at Google.

3. Emotional Risk

Will this create fear of rejection, judgment, or identity issues?

For leaving Google: I gave this a 3 (high risk).

My identity was deeply tied to being a “Google executive.” I worried: What if I fail? What if nobody wants to hire a 45-year-old who tried entrepreneurship and failed? What will people think when I leave this prestigious role to become a “starving artist”?

This was my highest risk category.

4. Financial Risk

Will this affect your ability to pay bills, save for the future, or maintain your lifestyle?

For leaving Google: I gave this a 2 (medium risk).

Yes, I’d lose my Google paycheck. But after talking to my financial advisor, I realized I needed less than half of what I was making to support my family.

I had plenty of runway. And I could always get another corporate job if things didn’t work out.

My total score: 7 out of 12 = Low Risk

Suddenly, leaving Google didn’t feel terrifying. It felt obvious.

Staying was actually the riskier choice!

Here are other examples I’ve mocked up in a spreadsheet:

Your Turn:

Pick something you’ve been avoiding because it feels “too risky.”

Score it 1-3 in each category (reminder 1 = low, 3 = high):

Physical Risk: ___

Cognitive Risk: ___

Emotional Risk: ___

Financial Risk: ___

Total: ___ out of 12

7 and under = Low risk (probably worth trying)

8 and over = High risk (proceed with caution)

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How This Helps You Get What You Want

When you break down risk into specific categories, you stop being paralyzed by vague fear and start making decisions based on data.

That “impossible” career change might actually be a 6 out of 12.

That “scary” conversation with your boss might be a 7 out of 12.

That side business you’ve been thinking about for two years might be lower risk than staying in a job that’s slowly killing your creativity.

Make the spreadsheet.

Face the numbers.

You might surprise yourself.