Every Career Choice Has a Hidden Cost
If you don’t decide what you’re optimizing for in your career right now, you’ll wake up frustrated by tradeoffs you never consciously chose.
Every role you accept optimizes for something and costs you something. I didn’t understand this at the time, but I can trace my own blind spot back to the moment I finally earned a role at Amazon.
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Live to Work or Work to Live
I remember how proud I was to get my Amazon employee badge. I had just joined a world-class team and I eagerly shared the update on LinkedIn. Finally becoming an Amazonian felt like validation of all the work I had put in and proof that I was winning the career game.
Then an older mentor left a comment:
“Congrats, Justin! Just don’t forget to work to live too!”
The advice felt trite and ill-fitting for a moment when I was celebrating a big win. My only focus was how to keep climbing the ladder and I dismissed the message as something people say who’ve already won.
It took me years to realize that “work to live” wasn’t a dismissal of ambition—it was a warning about unchosen tradeoffs. Careers aren’t just shaped by companies, roles, and pay, but by what we quietly give up to get them.
The Question You Should Be Asking
Every season of your life imposes constraints on what you can and should optimize for in your career. Most people, however, spend their time fixating on roles and companies while ignoring the more consequential tradeoff decisions underneath them. The real question you should ask is: What am I optimizing for in my career and what am I giving up as a result?
In practice, most people chase the shiny object or borrow their parent, spouse, or company’s vision for their career without considering what they want to make a priority.
I’ve summarized four career priorities below, including when it likely makes sense for you to pursue it and what tradeoffs it will require. If you want to dive deeper, there is a worksheet linked at the bottom of this post that will allow you to reflect and start making your priority intentional to start the new year.
4 Career Priorities
You can touch all four over a lifetime, but you can only optimize for one at a time.
Before you think about your next role, it’s worth naming which of these priorities you’re actually optimizing for right now.
1) Opportunity
Optimizing for a promotion, visibility or network growth.
When It Makes Sense: You’re early in your career or deliberately focused on expanding your reputation, network, or skills to take advantage of a unique opportunity. It may be that you want to work at a great company on the rise or choose a role that will catapult you to a new level of excellence. Molly Graham calls this a J-curve career move.
The Tradeoff: At Microsoft, I saw many people optimizing for opportunity. The issue is that these people build credibility inside their company, but weak networks outside of it. As your reputation increases, you become increasingly dependent on your manager, organization, and salary so pursuing a passion project or taking a parallel role (even if it better fits your skills or interests) is increasingly prohibitive. These opportunities are often highly demanding, so you have to be willing to pay the price of sacrificing personal time and flexibility for the opportunity.
2) Income
Chasing higher compensation or asymmetric upside.
When It Makes Sense: You’re intentionally building financial runway or at a place in life where sacrificing time for increasing financial reserves makes sense. It also may be the case that you’re required to pursue a higher income due to cost of living or personal obligations (paying off student loan debt, caring for an aged family member).
The Tradeoff: At Amazon, I watched (and experienced) how easily stress and long hours became normalized. Once equity starts vesting and lifestyle adjusts, it’s tough to choose a different role or take a step back when it means economic loss. Also, leadership is generally aware of how much everyone is paid, and higher pay often comes with higher expectations of being “always on” and available. Golden handcuffs can lead to a high personal cost to health, family, and loved ones. As Jon Bellion sung, “I know a lot of CEOs with billions and resentful kids, yikes.”
3) Flexibility
Choosing a job or company with options around hours, location, and remote work.
When It Makes Sense: You’re in a season when optimizing around family, health, or experiences is most important. If you have young kids and are in a two-income household, this priority can offer a lot of benefit for one or both partners. Alternatively, if you want to take 1-2 years and travel or experience the world, then a high flexibility role can provide a lot of value.
The Tradeoff: You’re willing to be the first to be laid off, the last to be promoted, and are in a place where flexibility is prized over higher earning or career development. Bluntly, this priority is riskier for people who are not yet mid-to-senior in their career and would limit this priority to 1-2 years for younger generations who want to grow their career over a long-time horizon. For the vast majority of people, early momentum still requires time, proximity, and sustained effort.
4) Stability
Reducing volatility, protecting against downside, and choosing a steady company/role.
When It Makes Sense: You’re deliberately prioritizing stability over growth to support caregiving, education, recovery, or a planned transition. It may also make sense if you are not looking to build your career but prefer a safe job where you can work 9-5, leave for the day, and not carry work home with you.
The Tradeoff: If you’re reading Career Field Guide, I’m going to assume that a small minority of you are going to prioritize this area. That said, stability trades optionality for predictability. In seasons of personal tumult or high obligations (death in the family, pursuing graduate school, or partner with a high-risk job), it can help to not have to think often about work-related stress. Also, if you’re nearing retirement, a stable job can keep you engaged while minimizing career-building expectations. That said, for early and mid-career professionals, stability can stagnate the development of new skills and make it tougher to take advantage of future opportunities.
What Are You Prioritizing and Does it Make Sense?
Clarity in your career comes when you name what you’re optimizing for and accept what that choice costs.
The goal isn’t to choose the "universally-correct” priority (there isn’t one) or to assume that the same priority must apply for an entire lifetime. The goal is to choose the right one for this season, on purpose, rather than inheriting it by default.
Put a meeting on your calendar right now for when you can take 30 minutes to work through this short worksheet and think through the season you’re in, what you’re actually optimizing for, and what you’re knowingly giving up as a result. While there’s no right answer, the goal is that you’re making these decisions on purpose. This type of work and alignment sets the foundation for a meaningful and rewarding career.
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