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Career

5 Questions to Weigh When at a Career Crossroads

For the first time in your career, you have options. And where you land and the work you do next will have a huge impact on your career trajectory. Jump on the right train by using this checklist to help make your next move.


This crossroad looks unfamiliar—for the first time in your career, you have options. You now have experiences under your belt, connections in the industry, and a work history that reflects your talents. This next decision is different than your first career decision because where you land and the work you do influences your trajectory.

If you jump on the wrong train without forethought or because you’re anxious, you waste time, or worse, you end up somewhere that’s difficult to find your way back. But because you’ve never been in a situation like this before, it’s time to cultivate curiosity and ask good questions.

Below is a checklist that will encourage you to be crystal-clear about where you stand when you are faced with the career decisions that need to be made in order for you to move forward.

Question 1: Who will I become if I take this opportunity?

In an interview with the prolific entrepreneur Seth Godin, Tim Ferris was curious about how Seth says yes or no to speaking engagements. Ferris wanted to get a better understanding of how Godin has deliberately shaped his long-standing and fruitful career.

Seth responded with a fantastic and simple framework: “What impact am I trying to make? And will this help me move things forward?” 

At first I believed that this was a framework that only someone as successful as Godin could use. However, you can distill his response into one key question that is applicable to anyone in the middle of their own crossroads: Who will I become if I take this opportunity?

Meaning: How will this contribute to my life’s goals? How will this open up more opportunities for improving my work? How does this connect to my values, my mission, and what I stand for?

The question behind the question is about understanding what kind of decision you’re about to make and the path it’s putting you on. Are you taking this next opportunity because of the pay or because working at that company will shape you into the person you want to become? (Neither is wrong! Just be deliberate.)

Question 2: What is the opportunity cost of this opportunity?

Opportunity costs are everywhere, and sometimes they’re hard to measure especially when you’re in the middle of career crossroads.

When Charles Darwin heard of the HMS Beagle and the voyage it was embarking on, he saw an opportunity to champion his curiosities about the world. The opportunity cost of not going would have been devastating because traditional education bored him and his environment was not nearly as rich as, say, the Galapagos islands, Brazil, or the Andes. 

While the endeavor was fraught with risk and possibly death, Darwin was compelled to go. An adventurer at heart, he sailed the seas for five years, collecting fossils, insects, and plants to help him devise a theory that would challenge deeply rooted ideologies and would ultimately change our world.

If he didn’t go, what would he have done instead? That’s opportunity cost in a nutshell. If you don’t take that job offer, what would you do instead? If you did nothing, what will that cost you?

This is also why I went from freelance to full-time. The opportunity cost of what I was continuing to do was no longer sufficient. The train slowed down. In order to level up and become the person that leads a career I desire, I had to hop onto a different train.

Question 3: What “frames” are around my options?

It’s easy to get fixated on a career option. Maybe it’s a prestigious company and just thinking about working there has your imagination running free.

The placement of “frames” around a potential decision influences how you act and what you can or cannot see. When you remove those frames for just a moment, you begin to see possibilities that didn’t exist before.

For example, if one of your career options is a remote position, the possibility of working from home sounds glamorous, but at what cost? Are you a person who thrives being alone all week or being surrounded by your team and grabbing a beer after work on Friday?

You want to ask yourself this question to create clarity in your reasoning to fully understand the impact of your decision. Why is your attention stuck on this picture? What happens if you removed those frames—what new insight reveals itself to you? What were you ignoring or missing?

Question 4: What sacrifices do I need to make if I take this opportunity?

Let’s say the options in front of you are glowing with potential—they demand your skills, the organization has a wonderful culture, and the role will challenge and push you to learn. But… you need to move across the country, make new friends, and pay double the rent.

When we laser-focus on the short-term discomfort, we willfully ignore the long-term gains. Challenging your biggest comfort zone and making difficult sacrifices is simply a part of life.

There are no right or wrong answer here. The goal is to be clear that these sacrifices, this decision, is the best possible route that will build the career and life you desire to lead. It’s hard to leave friends and family, the hometown which shaped you. And there’s the crux: stay in your comfort zone and make the best out of any opportunity that’s nearby, or venture into new territory and make your mark?

Question 5: Is it worth it?

Once you have an idea of who you will become and the opportunity cost of this next endeavor, you need to ask the grand question: Is it worth it?

You need to make a decision tree. A decision tree helps you see the consequences of your decision, the cost of resources, and chance events that may get in your way. It’s about being unmistakably clear about the decision you’re going to make so that (almost) nothing comes as a surprise.

You’re essentially asking yourself, If I take this route, where will this road take me?

You can probably imagine Darwin’s decision tree, if he made one. Stay at home or go on this ship? Be comfortable at home or face an untamable sea?

When we reach the end of our decision tree and know in our heart that the decision is scary but worth it, we should listen to the words of gonzo journalist Hunter S. Thompson when he said, “Buy the ticket, take the ride.”

What is the best piece of advice you’ve received that helped you make a tough career decision?

Paul Jun

Paul Jun is a writer and author. His latest book, Connect the Dots: Strategies and Meditations on Self-education, is available. His blog, Motivated Mastery, is where he connects the dots between subjects like mastery, philosophy, psychology, culture, self-awareness, and more.

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