Yes, You Should Have A Five-Year Plan

Having a good strategy is the starting point for your career or startup plans. Here’s how to picture where you’ll be in five years.

Yes, You Should Have A Five-Year Plan
[Photo: Flickr user Dineshraj Goomany]

“Where do you see yourself in five years?”


If any question ever felt like a trick, this one certainly does. Some days, it’s hard to say where you see yourself after lunch.

If it’s asked in a job interview, there’s a temptation to be less than sincere to land the gig: “Here at your company, of course, working tirelessly for you!” When you’re only asking yourself, five years from now can seem like a vast span of possibility or potential for change. Considering the changes the last five years have likely brought for you–new technology, unexpected life events, relocation, or finding a new passion–how can we say anything for certain about the next five?

Matthew E. May, author and founder of EDIT Innovation, reasons this necessary confrontation with the unknown in an article for 99u:

Here’s the thing: Your strategy is just a collection of guesses until they’re tested. There is real power in making bold assumptions, because you can turn them into clear hypotheses, and then scientifically test them in a rapid, iterative way.

May also outlines ways to nail down that five-year plan, while leaving plenty of wiggle room for change.

What’s My Wildest Dream?

The answer to this is what defines success for you, even if it’s on a grandiose level. Writing a New York Times bestseller, running a Fortune 500 company, or just owning a local shop that thrives for decades–your big, long-term goal helps guide steps you’ll need to take in the next five years. This isn’t the answer to the five-year question, but gives a target that can help narrow it down


What Am I Willing To Do For It?

This is where your strategy narrows. You probably already know what kind of bestseller you want to write, or what service your future-household-name company will provide. How you get there involves a process of taking jobs, starting projects and making moves to get closer to it. It also means saying no to things that aren’t within that field of vision.

In a 99u interview, award-winning illustrator Yuko Shizmu talked about her big dream to become known for her art, and what choices she made to get there:

Shimizu’s choice was commercial illustration for hire, not fine art illustration. She targeted advertising agencies and design firms. “[My work] is kind of specific,” she says.”So if the job doesn’t fit in the specific criteria they will call someone who does something a little more general. So it’s a decision you have to make.”

What Gives Me An Edge?

This isn’t a list of strengths and weaknesses, says May. Your skills are useful, but might be too common to your competition. Shizmu, for example, wouldn’t list her artistic skills as an edge, because her market is flooded with people who excellent artists. But her background in PR, that makes her better at self-promotion than the rest, makes her stand out.

After answering these questions for yourself, the next five years look a little more manageable–and you can answer that question confidently.

[h/t: 99u]

About the author

Freelance tech, science and culture writer. Find Sam on the Internet: @samleecole.