3 easy actions to clarify your career path

Yesterday I talked with a young guy who had never thought much about his career path. He landed an IT role eight years ago, and he’d been very happy in it until someone invited him to apply for a promotion into management.

He declined, but the unexpected opportunity made him think about “career path” instead of “job” for the first time.

He had no idea what a “career path” looked like or how he would plan one. But he felt he should have one, whatever it was.

As we talked, we uncovered a combination of things: He thought he had to make a decision between going into management or staying in IT, and he also felt a sense of urgency about it. He actually loved his current job and would feel like he would be giving up something great if he left.

And as for management, he had a limited understanding of what that really entailed in a day-to-day sense. He assumed it was mostly writing emails and doing performance evaluations.

It was easy to see why he was struggling with designing a career path.

There’s no such thing as a typical career path

Those of you of a certain age will remember Bil Keane’s Family Circus comic strip, and the dotted line path the kids used to run around the neighborhood.

My own career has been kind of like that. Wandering one way, then another, circling back, dodging traffic, petting a friendly dog, climbing over a fence, jumping a stream, saying hi to a neighbor…

Certainly nothing like the well manicured plot arc most of us imagine when we think “career path.”

People who haven’t been in the working world long still have a kind of “everyone knows how to do this but me” unease.

Like that first day of third grade when you’re told you will have homework, and you’ve never had homework before. How do you do homework? And did everyone else already know how to do homework? Oh, the anxiety of it all.

Or when you graduate college and everyone talks about career path.

The mythical career path goes like this: Entry level position. Increased responsibility. Supervisory role. Managerial role. Learn to play golf. Increased managerial responsibility. Executive role. Retirement.

Personally? I’ve made at least six major career shifts in 33 years. Not just changing jobs—changing my whole career path. From software development to tech writing to product marketing to web development to corporate responsibility to nonprofit leadership to executive coaching.

And this is not terribly unusual.

So when I talk with someone who doesn’t know where they want to go but thinks they should be committing themselves to a very specific career path, I don’t have any answers to give them.

But boy oh boy, do I have lots of questions.

How to get started when you don’t know where you want to go

My client’s biggest problem was not whether he should stay in IT or go into management. It wasn’t the ambivalence he was feeling, either. It was that he didn’t understand the roots of that ambivalence.

He knew he loved his current job, but he felt a vague pressure to make some kind of unknown change. So it looked to him like a choice between “staying in IT” and “going into management.”

And that leads into the first of my three actions you can take if you simply don’t know where to start in facing a career path decision.

1. Create more questions, not easy answers

When you’re unable to choose between two paths, the most obvious question to ask yourself is the one that’s also the absolute worst: Which path is best?

While that’s a terrible question to ask yourself (you are already mired in ambivalence, so all you’re really doing is creating guilt and shame by not being able to answer it), it’s an even worse question to ask someone else… because they will probably give you an answer.

It may seem counterintuitive, but when you think you need an answer, you may actually need more questions.

New questions can reframe the picture and change the process by which you make a decision.

Remember the scene in Lord of the Rings where Gandalf is trying to remember his way through the Mines of Moria? He pondered and pondered but couldn’t decide. Then he asked himself a different question. Which smells less foul?

Some questions you can get started with include these:

• Why is this decision important now?
• How does each path utilize my strengths?
• How does each path conflict with my personal core values?
• What pieces of information am I missing?
• In what ways would each path lead to my own personal growth?
• What pressures am I feeling from others, and what are their motivations?
• What in my upbringing, cultural background, faith, or other belief system is pushing me in one direction or another? And why? And how would it feel to go against that pressure?
• Who has done this before me, and what was their experience?

And my personal favorite:

• What other choices have I not thought of?

2. Make it a nonbinary choice

That last one is my favorite because there are never just two choices. There may be only two obvious choices, or only two viable choices, but if you think hard enough, there will always be at least one more option.

I’m so certain of this that I’ll send a Gray Bear journal to the first person who gives me a truly binary choice where there is literally no third option.

In any case, the point is to disrupt the cycle of flip-flopping by looking at the choice a different way.

The classic example of this is someone who is in a high-paying job they love, but the job is in a toxic workplace. Should I stay, or should I quit? That’s the question everyone gets stuck in, and even though you, as you read this, can immediately think of several other options, I guarantee when you’re in the middle of the crisis, you’ll most likely be stuck in the same “should I or shouldn’t I” quandary.

3. Ask someone who’s been there

One of my client’s worries was that if he stayed in IT, he might be missing out on important career growth. Even the language “stay in IT” and “move into management” suggest that one is stagnant while the other is progress.

But I know there are people at his organization who have been in an individual contributor role in IT for 20 or more years. I suggested he find a few of them and hear about their experience.

In my experience, a lot of younger workers are afraid to approach more experienced workers with questions like that. They don’t want to bother them. Or they’re afraid they’ll say no.

Some people definitely do not take informational interview requests. But I’ve found that most people love to be asked to talk about themselves and share whatever wisdom they’ve acquired over their career.

So don’t be afraid to ask them. Take them to coffee or send them a handwritten thank-you afterward—even a token gesture of gratitude goes a long way. Ask them about their own story—how did their career progress? How did they like it? What decision points did they face, and how did they handle those? What would they have done differently? What roadblocks or resistance did they encounter?

It’s always nice to end the conversation by asking them if there’s anything that you can do to help them. They’ll probably say no. Just be prepared to follow through if they say yes and it’s something you can do.

The best thing about decisions

The absolute best thing about career decisions is that you can always make a new one later. This gets harder as you get older—ageism is real—but I’ve found that younger people tend to put far too much pressure on every decision they make, as if it will define their entire life’s future.

Rarely is that the case.

No matter what you decide, I recommend that you always stay open to opportunity, and commit yourself to staying relevant. Even the most reliable jobs can disappear in a good economy, and resilience comes from staying sharp.

I can help

Have a decision you’re struggling with? A situation that seems untenable? A goal you need to define?

Set up some time to talk. I bet I can help.