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The Most Important Question to Ask When Making a Big Career Decision

Steve Schlafman
Steve Schlafman
5 min read
The Most Important Question to Ask When Making a Big Career Decision

Last week, I Zoom'd with a friend / mentee who is on the verge of negotiating a new compensation package with his employer. Given the impending negotiation, he's starting to think about his possible futures - both within and outside the organization. He wasn't sure how to proceed.

During our time together, he peppered me with questions to hear my perspective on his situation and potential paths forward. How should I think about compensation? How does it compare to industry benchmarks? Should I sign up for another 2-3 years? Should I think about making a change? What might come next? What should I do?

At the end of our conversation, I invited my friend to reflect on this question as a next step:

What do you want to optimize for in the next phase of your career and life?

Just about everyone I've coached knows this is one of my favorite questions. I often ask it to my coaching partners several times a day.

To optimize is to make the best or most effective use of a situation, opportunity, or resource. Focusing on what you'd like to optimize for helps you identify what's truly important and strip away the non-essential. In other words, it captures the essence of what matters most.

When faced with a big career decision like my friend, I usually suggest starting with defining what you want to optimize for and what's most important to you. In my experience, this is far more powerful than making a list of pros and cons.

It doesn't matter whether you're deciding to stay in your current role or evaluating multiple offers. Getting to the heart of what you want is vital.

So you might be wondering, how do I figure this out for myself? Where do I start? Is there a process to follow? How do I determine what to optimize for?

I usually recommend kicking off the process by carving out at least a few hours to go inward, reflect and journal. View this time as an investment in your career and future. In these sessions you'll begin to unearth the attributes that matter most to you.

Regardless of where you are in your career, there are dozens of attributes you can optimize for professionally and personally. Here are some of them:

  • Competitiveness: Is the company a proven or emerging market leader?
  • Leadership: Do I believe in management and their ability to lead?
  • Team: Do I like and respect the people I would work closely with?
  • Mission / Vision: Can I get energized by where the company is going?
  • Impact: Can I and the company have an impact on issues important to me?
  • Product: Does the product or service resonate with me?
  • Reputation: Does the company have credibility with customers and partners?
  • Compensation: Am I able to earn and save to meet my desired quality of life?
  • Benefits: How much do I value non-financial benefits?
  • Equity: How important is economic upside?
  • Growth: How much am I able to learn in this role?
  • Creativity: Am I able to create and express myself?
  • Role and Responsibilities: Does the role excite me and map to my strengths?
  • Title: Does the title reflect my role, contributions, seniority and aspirations?
  • Autonomy: Do I have agency over my work?
  • Work-Life Balance: How much do I value balance and boundaries?
  • Culture: Is this a culture that I'm attracted to and can thrive in?
  • Values: Does the company's values align with mine?
  • Stage: Do I want to join startup or more mature company?
  • Stability? How important is the stability of the role and/or company?
  • Power: Does this role make me important externally or internally?
  • Geography: Where do I want to live and why?

This list is by no means exhaustive, but should be a good starting point for you to reference.

When journaling, I recommend writing quickly and capturing your stream of consciousness. Don't judge what comes up. Write without editing or censoring. Remember, journaling helps the brain process and solidify information. Be open. See what emerges. Dive freely into each attribute that surfaces and calls for you to explore more deeply.

Once you've finished identifying the attributes that are important, it's time to review what you've written. What stands out? What are some common themes? What patterns have emerged? Were there any surprises? If so, what were they? What attributes are screaming for your attention? What have you learned?

Now here comes the hard and fun part: selecting and prioritizing the attributes that matter most to you. I recommend selecting no more than five. That doesn't mean that you can't value and honor other attributes. This step is a forcing function to help you gain even more clarity.

In order to narrow down the list, I suggest tapping into your core values. Remember, our core values highlight what we stand for. They guide our behaviors, decisions, and actions. When you know your core values, you can live in line with those values. This leads to greater fulfillment, purpose, and intention.

If you haven't identified your core values, here are a few prompts to help you tap into your them and surface your deepest needs.

  • What do I value most in my life and work?
  • What aspect of life and work give me energy?
  • What do I need emotionally and spiritually in the next phase of my life and career?

By now you should have a good sense of the top attributes you'd like to optimize for. If you're still not sure, I recommend taking a break.

Put it down. Step away. Go for a walk. Exercise. Cook a nice meal. A short pause may be what your brain needs to process the work that you started. When you come back to it, see what changes and emerges. This is very much an iterative process. Take your time with it and have some fun.

Remember, there's no right answer. This is a highly personal exercise. What might be relevant to your co-worker is likely different than what is relevant to you. What comes up in this exploration will be heavily influenced by your aspirations, needs, beliefs, values and life stage. Context matters.

I often recommend revisiting this exercise every six months. This will help you assess the quality of your decision and identify anything that has shifted. Most importantly, you'll get to know yourself better and hopefully make even better decisions in the future.

I wouldn't be where I am professionally without answering this question for myself. In fact, this process was indispensable when I was deciding whether to leave Primary and become a coach. I was able to strip away all of the noise and focus on what was most important at this phase of my life and career.

Just one year later, I've never been happier, more fulfilled and productive professionally. My situation is far from perfect but it's close. I'm doing exactly what I want in a way that aligns with who I am and what I value. That's the power of defining what you want to optimize for.

Next time you're faced with a big career decision and are unsure how to proceed, start by asking yourself the magic question: What do I want to optimize for in the next stage of my life and career? You might be surprised what you learn about yourself.

Godspeed. I wish you all the best on your journey no matter where it takes you.

CareerCareer AdviceCoaching

Steve Schlafman Twitter

Exec coach. Writer. Student of Change.


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