Career Evaluation: Taking Stock of Your Life and Work at Year’s End

The end of the year is a natural time to take stock of your life. Work is an important part of many people’s lives. As we enter the holiday season, I wonder if this isn’t a good time to ask: What do you want your career to do for you? Do you know what you […]

The end of the year is a natural time to take stock of your life. Work is an important part of many people’s lives. As we enter the holiday season, I wonder if this isn’t a good time to ask: What do you want your career to do for you? Do you know what you want to get out of the rest of your life — working or otherwise? Be honest in this career evaluation. Is where you are everything you’d hoped for out of a career? It might not be. But it might be the right next step toward what you want the rest of your life to be.

I’d like to help you think about what you want out of your time on the planet and how your career can be a tool to aid you in that mission. I don’t pretend to have everything figured out myself. But, as a professional on the other side of 40, I do have some 20/20 hindsight that can help.

It’s not about the job.

A job is seldom an end in itself. A job is usually a means to an end. It’s a tool to get something else you want.

When you get up in the morning and go to work as a developer, you aren’t excited about typing on a computer. You probably aren’t excited about reading documentation all day. If you do feel some excitement, it’s about the people you’ll get to do the job with or the prestige you’ll gain by doing the job well. You might enjoy the gratification of solving a tricky problem and feeling that you’ve helped others or the idea that you are adding to your personal legacy by creating something great. It’s not about the code — it’s about what the code enables you to do.

Or, let’s be honest, it may be about the money and benefits you get in exchange for your time, energy, and expertise. But the money and benefits are also a means to an end. They give you the freedom to be able to do the things you want to do.

This begs a scary and intimidating question: What do you want to do with your life?

Figure out what’s important in life and work.

These are important things to figure out regardless of where you find yourself on a life’s journey. You’ll spend most of the rest of your life working. Shouldn’t that investment of time and energy line up with what you want to accomplish? Early on in my career, a personal mentor led me through an imaginative journaling exercise designed to help me think about what I wanted to accomplish in life and who I wanted by my side.

The career evaluation exercise involved imagining my 80th birthday. My mentor asked me to focus on who was there. Who was sharing my life? On this important day, who showed up to honor me? Then my mentor asked me to imagine that the different people at the party got up to speak about the impact I’d had on them over the years.

For me, this exercise crystallized the idea that that forming a loving, supportive family was important to me. It also showed me that I wanted to be able to experience life with a significant other with whom I experienced a close, personal connection. I also discovered that traveling and living abroad were very important to me. Being in a position where I could be honest and transparent with those around me also mattered. Further, I realized that I liked building things that would make the world a better place. I also discovered that strong execution and follow-through helped me feel a sense of accomplishment.

I’d encourage you to take some time to engage in a similar exercise. It doesn’t need to take long or go into much depth. You’ll need a quiet place, something to write on, and about 30 minutes of time. You might want to take more than one try at this exercise. When you feel you have a pretty good understanding of what your end looks like, you’re ready for the next step!

Focus back on work.

Once you understand what’s important to you, you’ll be much better equipped to make decisions that align with those goals. One of those decisions is where you’re going to spend your career.

I would encourage you not to think about what sort of position you want in 20 or 30 years. That’s a long time horizon. Planning in decades has very little utility in the real world. Like the luminary Mike Tyson said, “Everyone has a plan until they get punched in the mouth.” Life has a way of punching us all in the mouth. Sometimes, life happens and things don’t turn out the way you thought they would.

Although you can’t know exactly how your career will end up, you can choose where you are now. And that choice can influence where you end up in 20 or 30 years. Make a choice that isn’t in line with your mission, and you could end up far off-course years down the line. If a ship’s captain is a fraction of a degree off in navigation at the beginning of a journey, that fraction of a degree turns into being hundreds of miles off-course at the end of a voyage.

Focus on your next steps, but keep the horizon in your back pocket.

As you think about where you want to work, consider the next five years: What would you like to be doing? Who would you like to be working with? Where would you like to be? Five years is a short enough time span that you should be able to take your first step with that realistic end in mind.

A lot of books have been written about how to check in with yourself, evaluate the course of your career, and measure your progress toward far-off goals. But as you take stock at the end of this year, set the furthest horizon at five years. Then think about what the best next step will be to reach that horizon. This way of thinking is both lightweight and purposeful. It doesn’t have a lot of everyday overhead, but it allows you to stay focused on the next major stage in your journey toward your goals.

Annual career evaluation is a key practice.

Taking time to look strategically at what we are doing with a majority of our waking hours is a key practice to take part in at the end of every year. Hopefully, this rough outline for career evaluation is helpful in your process of finding your way.

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