Learn First, Plan Later: Drafting a Useful Five-Year Plan

Ten years ago, when I was a newborn lawyer, I inveighed against personal five-year plans. The crux of my argument was that life is like the weather: largely predictable in the short term but increasingly unpredictable in the long term. Indeed, five years before writing an essay on the topic, I wasn't even thinking about law school. Since I couldn’t predict my decision to go to law school or anything else that happened in the preceding five years, I concluded there was no point in anyone trying to make predictions that far out.

Five years later, I happened upon the first article and thought it would be fun to follow up and see whether my thoughts had changed. They had, somewhat. I now thought novices shouldn’t make five-year plans. Instead, they should learn as much as they could before making definite career plans. Without experience, they would expect to produce plans laden with easily filled holes. Only once they had some experience in their chosen field should they consider planning. Again, this opinion was informed by a sample size of one.

When I finished, I created a calendar notification to remind me to write what you’re reading now. After all, who doesn’t love a good trilogy? Ironically, (1) I made a five-year plan without realizing it, and (2) it turns out neither article I wrote about my experience properly addressed the issue. Let’s see if I can do better this time.

The idea of five-year plans has been with us since at least the 1800s. Early invocations of the term seem limited to government planning, and the phrase reached its first peak of popularity soon after the introduction of Stalin’s first Five Year Plan in 1928. Its second, much higher peak was in 1958. Credit for this peak and the idea’s current popularity is often given to Peter Drucker, whose book The Practice of Management was published in 1954. In 1973, occurrences of “your five year plan” started to overtake occurrences of “your Five Year Plan,” perhaps signaling an integration of the phrase into everyday speech. Today, the question “where do you see yourself in five years” is common to the point of cliché. But is a personal five-year plan useful?

It is well established that setting goals positively impacts performance. But there are caveats: Specific, hard-to-accomplish goals lead to better performance than easy or vague goals. Striving to master a task or skill, and doing it because the goal or task is something you’re interested in, also tends to garner better results than working for external rewards.

A plan’s purpose is to make achieving a goal easier. It can also help one determine whether a goal is worth pursuing at all. A dream job as the Richmond Flying Squirrels mascot, for example, might be a bad idea for someone who dislikes wearing costumes. Plans can help one determine why, when, and how to act on a goal. However, odds are good that most personal career plans do not.

One issue is that we tend to borrow ideas from others. As a result, a typical five-year plan tends to be a short list of jobs, and tends to sound like every other five-year plan. For example, one will often hear a business or law student say they plan to work for a big firm for “the experience," then move to a smaller one for “the lifestyle.” But, in this case, is step one necessary? What if the hiring managers at the small firm don’t care about big-firm experience? Sure, some do. But a few phone calls or emails to HR in advance might save students a few years.

Failure to research can also impact someone mid-career. Let’s say you earned a Bachelor of Business Administration degree and get a job in a large financial firm. You later learn an advanced degree is necessary to move up in the company. Do you choose a Master of Science or Master of Business Administration?

Many people choose the MBA because of its prestige. However, in this situation, that leads to retaking classes you took as an undergraduate because MBA programs are geared toward people without a business degree. Choosing an MS instead will likely allow you to skip a year or two of classes. Either way, you end up with an advanced business degree, and the hiring managers might find either option acceptable. Again, a few conversations in advance of making a decision can help with goal setting.

Career Essential Reads

Ambiguity at Work: How Your Approach Shapes Your Success

The Rise of "Quit and Staying" as Workers Return to Offices

Another issue is experience. Better information leads to a better ability to plan, and someone with a few years of experience under their belt will not only be able to create more practical plans than a novice but they’re also more likely than a novice to have access to tools and connections to help achieve whatever goals they set for themselves. These factors may help explain why the average age of a successful entrepreneur is 45.

Building a plan that’s useful to you may take some time and introspection. Fortunately, research suggests that people who engage in a “sampling period” of gaining generalized experience before specializing tend to do better in the long term than their colleagues who specialize immediately. This is partly because generalists learn additional skills that can be integrated into their work and partly because they tried a few things before settling on a path of their own choosing.

Of course, a plan need not be published in a leather-bound 100-page notebook with charts and footnotes. A scrap of paper that says, “get job, work 20 years, collect pension” can be a perfectly fine and complete plan. But if you have a goal with a lot of moving parts, you may want to consider planning—not five years out, though. Take one step at a time, starting with "why." After all, the future may have plans for you.