I’m excited to welcome Bracey Halbrook as a co-author for this next blog post in the series on Making Better Career Decisions[1] . I first met Bracey when we were working together at a large healthcare company. Bracey operated on the finance and operations side of the business, and I always admired his sharp, analytical thinking. Eventually, we both moved on from that company, and Bracey transitioned into the consulting world.
A few months ago, we grabbed lunch to catch up. He started sharing how he was helping a family member think through a major career pivot using a surprisingly formulaic approach. It is the exact same method he has used to guide his own successful career moves over the years. Because we are in the middle of a series on how professionals make job changes, I asked him to pull up a proverbial chair and unpack his “left-brain” blueprint for us.
Why Career Decisions Feel So Heavy
One thing I (Kent) have learned after hundreds of recruiting conversations is that very few people struggle because they lack options. They struggle because every option comes with tradeoffs.
Should I take more money?
Should I stay because I love my team?
Should I risk leaving a stable company?
Should I wait another year?
I have watched hundreds of professionals fall into analysis paralysis. In some cases, that overwhelming feeling comes from trying to find the single “perfect” move.
Shifting Your Mindset About Career Decisions
Early in my career, I (Bracey) realized the value of thinking differently about career decisions. After making a handful of strategic job changes over the years, I stumbled upon a phrase I’ve used dozens of times in conversations with family members and friends that are trying to make the best decision about a new job opportunity:
“Your career isn’t one giant decision. It’s a series of strategic decisions that open pathways to future opportunities.”
That simple shift changes everything.
In finance, we do not view investments as a guaranteed, singular outcome. We view them as opportunities with uncertain outcomes. Then we decide whether or not to invest. Your career is no different. It is a series of strategic choices using probabilities and expected values.
Instead of relying purely on gut feel or hyper-focusing only on the best-case scenario, you can make highly rational decisions by estimating the true mathematical value of a move. This approach strips the panic out of job hunting. It changes the question from “Is this job perfect?” to “Is this a smart decision based on my current viewpoint and long-term goals for my career path?”
The Five-Step Framework for Making Your Next Career Decision
To look at a career move objectively, I (Bracey) created my own personal Strategic Career Design Framework. Over the years, it’s helped me and others I know make better, more thoughtful decisions when it comes to career opportunities. And the good news is that you do not need an advanced degree in statistics to use it.
For any major career decision, I walk through five simple steps to create plausible scenarios and calculate whether a move makes sense:
1. Define the Time Horizon
Do not try to look 20 years down the road. The market changes too fast. Instead, decide on a realistic time frame that you want to judge the move from. Maybe it’s 2-3 years. Maybe it’s 5-6.
Ask yourself: “At the end of this time frame, what would make this move worthwhile?”
That simple exercise creates a surprising amount of clarity in comparing your current job with a new opportunity.
2. List Distinct Outcomes
Within your timeline, identify three to four plausible outcomes for the new role. Instead of assuming everything will go perfectly, write down several realistic possibilities.
Here are a few examples that you could build from:
- The new company has opportunities for you to get promoted quickly or the company grows.
- You will stay at the same organizational level, but you gain steady skill opportunities and stable compensation.
- The culture is a better fit and you have a stronger quality of life.
- The company underperforms or funding doesn’t come through and you find yourself laid off or looking again in a year.
Then bucket your outcomes into three categories: best-case scenario, most-likely, and worst-case scenario.
The goal isn’t optimism or pessimism. It’s realism.
3. Assign Probabilities
Based on the data you have gathered during your interviews and market research, look objectively at the company and assign a realistic percentage to each outcome.
- Maybe your best-case scenario has a 20% chance.
- Perhaps the most likely outcome is closer to 60%.
- The worst-case scenario might only be 20%.
Just make sure your total equals 100%. This forces you to separate what feels scary from what’s actually likely.
4. Score Each Outcome
On a scale of -5 to +5, rate the value of each scenario. Do not just look at salary. Base your score on factors like compensation, skill acquisition, lifestyle, advancement opportunities, network growth, and how well the job aligns with your personal values. A great culture might score a +4, while getting laid off in the worst-case scenario might score a -4.
5. Calculate Expected Value
Now, do the quick math. Multiply each probability by its corresponding score and add those numbers together. The final number is your Expected Value. You can run this exact same math on your current job to get a baseline number, and then compare it directly against the potential new opportunity.
A Quick Example of Running the Numbers
Let’s say you’re deciding between staying in your current role or accepting a new opportunity. On paper, staying put feels “safe.” But after working through the framework, you might realize the numbers tell a different story.
Analyzing Your Current Job
| Outcome | Probability | Score | Expected Value |
| Best-Case | 10% | +5 | 0.5 |
| Most Likely | 80% | 0 | 0 |
| Worst Case | 10% | -4 | – 0.4 |
When you calculate the expected value, the result is only +0.1.
Analyzing a New Opportunity
| Outcome | Probability | Score | Expected Value |
| Best-Case | 60% | +5 | 3.0 |
| Most-Likely | 20% | 0 | 0 |
| Worst Case | 20% | -4 | -0.8 |
Even with more risk, the expected value jumps to +2.2.
Does that guarantee the new job is the right decision? Of course not. But it gives you a much more objective way to compare the opportunities. Instead of asking, “Which option feels safer?” you’re asking, “Which option creates the greatest long-term upside based on what I know today?”
Taking this objective look helps you spot where you might be over-weighing a flashier, low-probability opportunity, or under-weighing a stable, high-probability opportunity with massive long-term upside.
Remove the Panic & Paralysis of Career Decisions
What I (Kent) appreciated most about Bracey’s framework wasn’t actually the math. It was the discipline.
As a recruiting leader, I often tell candidates to think beyond salary and recency bias. This framework forces you to do exactly that. It slows the conversation down. It removes some of the emotion. And it helps you compare opportunities using the same criteria instead of whatever you’re feeling on a stressful Tuesday afternoon.
Bracey would be the first person to tell you this framework isn’t meant to replace intuition. You need to acknowledge your own psychological tendencies and see how they might factor into your scoring system. For example, if you are naturally risk-averse, you might score a “worst-case scenario” way lower than it actually deserves. Recognize your personal risk framework and be honest about how comfortable you are with uncertainty.
There will never be a formula that guarantees the perfect, stress-free career move. Life doesn’t work that way. But there are better ways to think. That’s what I appreciate most about Bracey’s framework. It gives you a repeatable process you can review and update over time as you learn, grow, and collect new data points. The goal here isn’t to find an absolute guarantee. The goal is confidence—the confidence that comes from knowing your next move will make a positive difference in the long-term value of your career.
By Bracey Halbrook & Kent Wilson
Bio for Bracey Hallbrook:
Bracey Halbrook is a seasoned executive in finance and operations, currently serving as Chief Financial & Operations Officer at rule of three, LLC, a healthcare advisory firm dedicated to collaborating with organizations across the industry as they navigate today’s complexities and achieve progress toward a high-value and sustainable tomorrow. With 25+ years of experience, Bracey brings expertise in healthcare finance, planning, and consultative analysis to deliver measurable improvements in revenue and profitability. His prior experience includes leadership roles at Ardent Health Services, HCA Healthcare, and Parallon. A Tennessee native, Bracey has earned a Master’s degree in Healthcare Administration from the University of Saint Francis and a Bachelor’s degree from the University of Tennessee, Knoxville.