You’ve Got Five Years of Experience. Now What?

Five years ago, I wrote a piece titled Skip the Five Year Plan – Try These Two Avenues to Success Instead. That article questioned the wisdom of pressuring novices to map out a career before they’ve been on the road long enough to know the lay of the land. To support my argument, I guided the reader through the wanderings of my previous five years: First, I wasn’t going back to school. Then I wasn’t going to law school. Then I was going to law school and I was going to be a public defender. Then I opened a law firm.

Running my own business was a pre-law school dream. I prepared for years. I earned a finance degree. I worked in management and sales positions. I was simply waiting for the right opportunity to come along, and as law school progressed, I realized more and more that opening a law firm was going to be it. So in my last year, I started planning. I was ready for everything. Except that I would hate everything about it.

My plan was stained with inexperience and ignorance. Earning startup funds from short-term jobs as an independent contractor? Mind-numbing. Learning from other lawyers by doing small jobs for them? Blemished by technology. Taking on my own cases? Tarnished by clients who vanished, leaving nothing but dust and unpaid bills. I should’ve listened to my own advice.

Looking back, hating my creation was predictable. I had easily identifiable holes in my plan. I never considered what I enjoyed doing. My mom told me I wouldn’t like doing mindless work for a year. I brushed it off. I never asked any lawyers whether they needed the services I was offering. A few phone calls and I’d have known the answer was “no.” I was, however, prepared for the fact that some of my clients would try not to pay. Intellectually.

I was prepared to run a business, but I wasn’t prepared to run a law firm. I didn’t know what to expect. I needed time to learn what I didn’t know and couldn’t anticipate. Just a few years of experience would have dramatically increased my chances of success. Planning before I gained this knowledge was a mistake.

Were I to rewrite the article today, I’d make the same argument I did then – novices need to learn everything they can. Every other plan can wait.

However, my classmates and I now have five years of experience. Some realized they didn’t want to be lawyers long ago. Some love what they do. Some are writing blogs you should definitely tell your friends about. But it seems most are asking, “What next?”

This is understandable. Humans adapt to almost anything. We like novelty. Forty hours a week times 50 weeks a year times 5 years equals 10,000 hours of doing the same tasks. It takes 10,000 hours of deliberate practice to become an expert at something. But even without the intense focus and mentorship of deliberate practice, someone who has worked at a job for five years knows most, if not all of what there is to know about that job.

So many of my friends, along with a lot of other fifth year folks, are looking for something new. But what, and how?

Situation #1

Let’s start with the most dramatic shift possible – a career change. You hate the job. You hate every variation of the job. It sounded like a good idea, but it’s just not a good fit. So you’re ready to find something else. A good way to start is by taking a career test. That’s how I became a lawyer. I took the test at a few years back. It’s a pretty simple setup – you answer a series of questions for about half an hour and they rank 900 jobs in order of what your answers suggest you might like. It was $20 when I took the test, but their pricing has changed. With that in mind, you may wish to consult your alma mater’s career center and see if they have a version of the test you can take for free.

Your results are a prediction of what you might like based on what you told the computer you do like. So, you’ll see some things you might be interested in, some things you’re definitely interested in, and some things that you don’t know anything about. When that happens, you can read up on those jobs in the Bureau of Labor Statistics’ Occupational Outlook Handbook. The information in the OOH will give you a good idea of what you might like, how much you’ll earn, and what steps you need to get there.

Situation #2

In contrast to the first example, let’s say you like your job. You don’t want to leave, but it could be better. In that case, you may want to try customizing your job, or job crafting.

The term job crafting describes the steps people take to customize their jobs to better fit their motives, strengths, and passions. For example, many organizations have an “event planning person,” who organizes birthday parties and other celebrations. This is usually a role someone takes on, but not part of anyone’s formal duties.

People redesign their jobs by taking on more roles, but they may also take on fewer roles, change their interactions with people, or change the way they think of a job. We even customize our jobs where there is little room for change. People working in call centers are glued to their desk, often repeating prepared scripts for hours a day. In this situation, one may start to view each call as a performance, trying out different characters to make the day go by faster.

A more detailed guide to the theories behind job crafting is here. It discusses the benefits and challenges associated with job crafting, and encourages employers to recognize that people naturally shape their jobs to suit their needs. Some of this customization is useful to the company. Employers are encouraged to utilize what works well rather than limiting employees to the formal duties set out for them.

Situation #3

Of course, you might not be looking to change industries or increase your satisfaction at your current job. You might be looking for your next step, regardless of what that is. This is where mentors and headhunters come in.

The issue, of course, is that you’re a person, not a list of bullet points. Résumés tell a potential employer what you’ve done in the past, and suggest what you might be good at. It doesn’t necessarily tell you or an employer whether you’re a good fit for a new role. But we often don’t know the answer to that question ourselves.

This is the advantage of speaking to someone with more experience than us. A mentor can inform you about the road ahead, suggest organizations for you to join, and make introductions. A headhunter gets paid to size up peoples’ résumés and personalities and choose persons who are a good fit for a particular job. In either case, this outside voice can point you in a direction you may not anticipate, but is a better fit than what you pictured for yourself.

If you don’t have a mentor and can’t get a headhunter to speak to you (this happens and I haven’t figured out why), you can always ask for informational interviews from people who are doing a job you’re considering. How do you get an informational interview? Just send an email. Seriously. Let them know who you are, where you’re at in your career, and what kind of information you’re looking for. I’ve emailed a lot of people for various reasons, and most are nice enough to share information or speak with you if you ask. I’ve even made a few genuine connections after speaking with people in person or via email. It’s a great tool if you have no or few connections in an industry.

Regardless of where you are when you start, you’ll eventually make a decision. When you do, I suggest taking advice from the Ask the Headhunter website. I’ve read Nick Corcodilos’ posts on the PBS Newshour website and I’ve become a fan. Among other things, he (and others) notes that most people find jobs through personal connections. Some of those personal connections are friends or classmates, but often, they’re people in the same industry as you.

Where do you meet these folks? Conferences, industry events, places like that. “Network?” Oh, no. Making connections takes time. I have a stack of unused business cards from people I’ve met at networking meetings who I’ve never contacted and who have never contacted me. In the meantime, I got my last two jobs because friends thought of me when someone asked if they knew anyone who might be a good fit for the job. You make connections the same way you did when you were a kid – you see people a few times in different contexts and start talking to them. Friendships form on their own from mutual interests, mutual jokes, and mutual friends. In the meantime, develop a good reputation for the quality of your work. Friendship and a good reputation trump networking.

For the most part, these situations do not require a five-year plan. If you want to attend law school, for example, your next five years are already planned for you (Taking the LSAT, applying, and waiting for first day of school is one year, law school is three years, and then you have to wait to be licensed, even if you’ve secured a job). Building many strong connections so that people think of you when a job comes up might take five years, but I’d say “probably less” for most of us. But some plans do.

I started working on my speaking career back in 2016. I spent a year working with a speaking coach (I anticipated two years). I spent the last two years writing this blog, working on my writing skills and my writing voice (I thought this would take one year). I anticipate another year or two of trying to publish magazine articles to build my audience. And I have goals further down the line. While it may look like a five-plan, it’s really been me taking yearlong steps and at each step asking, “what’s the next thing I need to do to reach my goal?” I have my eyes on a long-term goal, but each goal is a goal in itself, and I do my best to keep my mind on where I am and what I’m doing. And because things change along the way, I reevaluate at each step. Sometimes the “final” goal changes, sometimes it stays the same.

With five years of law and three years of public speaking preparation behind me, I find myself still against five-year plans. I am, however, a fan of long-term goals without artificial time pressures. Part of the reason for this comes from a story I heard from an interview of a screenwriter on YouTube. He was asked, “What’s the best advice you received but didn’t take?”

He said that after he sold his first script, an agent told him that studios would start asking him to write other movies, and that his choice would determine the path of his career. One the one hand, he could take whatever came and be known as a guy who writes for money. On the other hand, he could wait as long as it took to find an idea he really wanted to write about. If he held back and waited for this script, he’d be able to write whatever he wanted. The agent advised him to wait.

He succeeded, for a while. But eventually, one company offered him more dollar signs than he had ever seen. He took the money. He still had a lucrative career, but not the career he could have if he waited for the right project. If you create a five-year goal for yourself, you may rush into something that’s not right for you because your plan demanded it. On the other hand, you might spend years waiting to do something you’re already capable of or simply hate. It’s better to remove the time element. Instead, figure out what you want. Is that more responsibility or an entirely new career? Then, figure out what you need to accomplish before you can start working on this primary goal. Reevaluate after completing each sub-goal to see if the long-term goal is still something you want. If you find yourself no longer interested in a particular goal, you can start the process over before you feel like you’ve gone too far. After all, things change. And your more informed decision is likely to be the better one.

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