Map Out a Plan, But Shift Course Often

You wouldn’t leave for a hiking expedition without a map (or at least a smartphone with GPS). Why embark on a career without one?
Maps help us to visualize where we’re going, and there is something very powerful about visualization. Golfers try to visualize the ball on a perfect flight—landing exactly where intended—before they even attempt to hit the shot. Olympic ice skaters see themselves landing the triple axel before they’ve even laced up. If we can see it, we can often do it.
The same goes for your career. You need to imagine it before you do it. If you’re still early on in your career, think about what your life will look like at forty. If you’re forty today, try to visualize what you’d like sixty to be like for you. And then write it down. And be specific. What exactly are you doing in twenty years—working for your dream company or maybe owning a business of your own? What do your days look like? What are you spending the bulk of your time doing? Hopefully, it’s something that you love and are pretty darn good at.
Now what? Figure out how to get there. Look at the period between now and then and map out exactly what it will take for you to get to that goal. Do you need a degree in graphic design? Do you have to learn how to code or earn a professional degree? Are you in the right geographic location or do you need to move? Do you know the right people, or do you really need to invest in your network? By mapping out how to get “there” from “here,” the steps that you need to take will become that much clearer. And with a solid long-term plan in place that is then broken down into short-term, achievable goals, it is almost unbelievable how much you can accomplish in just a few short years.
But there’s a problem. How can you reach the promised land if the destination keeps changing? And it will change. Your “dream career” will likely look very different when you’re forty than it does when you’re twenty. You will have seen more options; you will know yourself better, and your priorities and views on life will likely have shifted. The world does not remain static either. When I was twenty, the list of things that didn’t exist (at least in the mainstream)—smartphones, Kindle, Facebook, Twitter, YouTube, podcasts—is almost comical. Today, these innovations form a substantial part of our economy and the bedrock of millions of people’s careers. There would have been no way in 1998, for instance, to describe a 20-year career goal as: “be a well-known e-Book author and podcaster, with a large following on Facebook and Twitter.”
So, you need to change. You need to be conscious of your surroundings—in the form of new industries and opportunities arising—and you need to be conscious of your own interests. And your interests will change. Over the course of your career, different subjects will light your fire. You need to pursue them. These are the areas, to be cliché, that don’t “feel” like work, but rather, you’d do them even if you weren’t getting paid. Maybe that sounds too good to be true, but I’ve personally had many over the course of my career. I was dazzled with the world of finance and investment banking in my twenties. I read every book I could get my hands on, pursued every degree I could (hence the MBA and CFA), attended every drinks event I was invited to you and didn’t bat an eye at working 12-hour days. I was “in it” and loving it.
Later on, while benefiting from all the knowledge I had picked up in the investment banking world, my interests shifted to marketing, writing, videography, and podcasting—basically, I became infatuated with storytelling. Again, I dove in deep. I wanted to read every book, listen to every podcast, and build my network. And it’s true, while you’re in it, while you’re completely infatuated with something, it doesn’t feel like work; it’s thrilling and it’s personally (and hopefully professionally) rewarding.
So, am I giving you conflicting advice by telling you to have a 20-year plan but then go wherever the wind blows with your short-term interests? I hope not. I think you need to know where you’re going, and, in some way, shape or form have a “true north” or “guiding light.” Having this direction can help you decide if a particular choice in the short term gets you closer to that long-term goal or not.
But you need to listen to yourself. Your gut will guide you to your areas of passion. And building expertise in these areas will be much easier than laboring over something you really don’t enjoy. And that’s one of the things I love about this philosophy of having a long-term goal with a willingness to both change that goal and to follow your current interests. It’s a more sustainable path. You are so much less likely to get burned out if you’re spending your time in the places that light your fire. And in this marathon, we call our careers, you need to keep it interesting.
So, don’t wander aimlessly through your career. You’ll probably end up in a place you don’t like. Map out a plan. Follow it but be ready to change—and you may need to change quite often. If you can remain flexible and follow your interests by throwing yourself completely into them, I think when it’s all said and done, you’ll have an impressive list of accomplishments that are rewarding both personally and professionally—or in other words, you will have built a fulfilling career.
This article is an excerpt from my recently published book, Say Good Morning Like a Human: 50 Unwritten Rules for Surviving the Modern Workplace and Building a Career You Love.