Why Entrepreneurs Need Career Plans

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All too often I hear the refrain, “Career planning isn’t really applicable to entrepreneurs.” We commonly think of a career plan as a tool for climbing the corporate ladder. When you’re at the top, there’s nowhere else to go, so what’s the point of learning how to climb? Such thinking misses the point of what career plans are really about. Everyone, including founders and CEOs, needs a career plan.

I’ve long noted that your career plan needs to encompass more than just your job, and certainly more than your job title. The starting career plan questions I recommend are as much about your needs in life as they are about your job. Regardless of your title you need to think about the impact of your job on your life.

When we think about our jobs, they are not just a source of money. They can also provide happiness, engagement, challenge, motivation, satisfaction, a sense of purpose, socialization, and other non-monetary benefits to us (or a lack of any of those).

For some people, a single job may offer that for years on end; others need new challenges. Consider this exchange on Law & Order between white shoe law firm partner Rebecca Shane (Kathleen Turner) and New York City ADA Jack McCoy (Sam Waterson).

Rebecca Shane: You know, our firm is thinking about expanding. Have you ever considered private practice?

Jack McCoy: Considered it and dismissed it a long time ago. I've accepted my place in the world.

Rebecca Shane: I suppose that's a virtue, although personally, I can't see it.

Jack knows who he is; he is and will be content with what he does. For Rebecca there’s always new mountains to climb.

Even if you are a founder or CEO, you probably don’t want to be static. You may want to expand your company in terms of revenue and headcount or evolve in other ways. To do this you, like your firm, need to develop new skills. Your title may not change, but you certainly need to. Running a team of twenty employees with a handful of local clients is very different from running a company of a thousand doing business across multiple continents. Career plans are about growth, be it your job title or other things like career skills.

You may also find you want to take on other roles. Some CEOs may dream of the same role but at a bigger organization. (Ask yourself, if Alphabet reached out to you to be their CEO, would you leave your current job for it? If so, then you’re open to other jobs; you may want to be more proactive instead of just dreaming whether it’s a new role at a new company or evolving your current role to be that dream job.) If you’re a founder, you may have an exit plan in mind and will look to build another company down the road. You may not interview for it but other skills like networking and leading will help you be successful. Many founders and CEOs, either after stepping down or while still running a business, are interested in serving on a board of directors. It may not be full time, but it is a job, and you need to network, interview, and qualify to get those roles. Like any other job, having a plan helps you succeed.

Even if you find yourself in the same shoes as Jack McCoy and will work happily ever after in your current job, that doesn’t mean you can rest on your current skills. The DA’s job may not change, it’s leading the team of ADAs to prosecute criminals, but the environment in which it happens does. Many founders and CEOs needed to learn to manage a virtual or semi-virtual team in 2020. Over the prior thirty years other changes have included internationalization and outsourcing, thinning middle management, working with cross generational teams, and increased use of technology. Some skills are mechanical, like learning international contract issues. Others are interpersonal, like managing people by video. Growth is necessary, one way or another.

Whatever your goals, the key point is that a career plan isn’t just about a job title. All of us need to grow and evolve; while that may be a title for many, for others it could be a new challenge or area of focus in our jobs. As with any future desired career state, simply wanting it isn't enough, success becomes much more likely when we proactively plan, execute, and reflect.

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