Navigating Through a Meandering Career

Problem

I’ve been in many conversations with product people who think about their careers as roadmaps. Thinking about your career like a roadmap assumes you know where you want to go next or where you want to end up, which means you can then figure out the steps necessary to get there over time.

This approach works for a lot of people, but it’s not how I understand my career path. And worse, for some folks, it can be a really intimidating way to think about their professional path.

I want to empower people to think about their career and development in the workplace as something that can meander and take various forms and shapes over time. It is okay not to know where you want to go next or where you want to end up! It is okay to embrace uncertainties and emerging opportunities. Often this feels like moving against a current in a culture that values certainty and confidence. Knowing where you want to go and what you want to do can be incredibly valuable, but it is also okay not to have all those answers all the time or right away.

"I want to empower people to think about their career and development in the workplace as something that can meander and take various forms and shapes over time."

"It is okay not to know where you want to go next or where you want to end up! It is okay to embrace uncertainties and emerging opportunities."

Actions taken

I’ve shared this perspective on career meandering with other product managers and aspiring PMs and found that many others feel similarly. For some, a candid exchange about how it’s OK not to know what’s next brings an immediate sense of relief and serenity. When I started out, I had no idea what I wanted to do. I tried different things, stumbling along the way. In the meantime, I learned that meandering through a career allowed me to explore what I liked and didn’t.

Recently I had a conversation with a friend who works in product at a large company and was struggling with whether or not they were in the right role. During our conversation, they outlined potential paths they could take with a somewhat self-judgemental tone. My response was to comfort them by telling them how it is okay not to know where you want to go. It is okay to not want to strive for a role that our culture defines as the “next step up” on a corporate ladder. They were relieved to hear that perspective. In their view, their friends from college and grad school who had gone into product had more “type A” visions of their careers, distinguished by a hierarchy of choices and emphasis on a linear path. But it doesn’t always work like that for everybody.

I see the effects of a roadmap approach to a career daily. Folks coming out of school and getting started in product face an enormous amount of pressure. They are expected to know what position to aim for and to land something that feels prestigious. I wish I could take that pressure off. I remember having a panic attack after going to my college career center because thinking about the future felt so high-stakes. Not being able to pinpoint what I wanted was incredibly stressful. I wish I could go back and tell myself that taking what comes is an OK way to go, and exploring potential career choices with a curious mind and wandering spirit can actually be more fruitful than planning. I wish I knew it was okay to follow my instinct, react, and then course-correct based on those reactions. That’s what ended up happening for me eventually.

My own path is full of meandering. I got lucky and landed a nonprofit job during the Great Recession, where I ended up falling into social media and communications. Then I got really interested in bicycle policy and found an opportunity to lead communications at two bike advocacy organizations. Those jobs entailed building websites and online tools, which ended up bringing me into a startup – first working in operations and then, gradually, to a formal product role. The story has a logical thread in retrospect, but at the time, I was just taking some opportunities that came up, saying no to others, and staying curious. Not because I knew where I wanted to go, but because I was open to possibilities.

If you’re interested in embracing meandering in your professional path, I suggest questions like this when you reach a career crossroads:

• What have I liked working on in past projects / positions?
• What did I dislike?
• Who do I enjoy being around and working with?
• What questions can I ask them about their experience in their roles? How do they approach their career?
• What are potential areas I might be interested in? What are the roles that include working in those areas?

Lessons learned

• If you find it difficult to think of your professional path as a series of logical steps, consider letting your “planning mindset” go and nurturing a curious mindset instead. When we develop plans, we create idealized versions of how things will look and feel. What actually happens often differs from our expectations. Even if you plan, you will probably be surprised by what you encounter. I recommend maintaining a dose of “I am going to see how I feel about that” or “I am going to see what I like/don’t like about this.” This leaves yourself open to your own honest reactions to what’s happening, rather than focusing on comparing an outdated plan to the landscape you encounter.
• The world is immense, and there are so many opportunities out there, regardless if we can see them or not. The book Mindset: The New Psychology of Success by Carol Dweck is a compelling account of what people can do when they put their mind to it. How can you approach your career as a learner, open to growing and enjoying challenges?
• Planning and understanding a career as a series of predefined steps is absolutely valuable to some. That model even allows for taking one step backward in order to take two steps forward. But if you’re one of the folks for whom that model is intimidating, take heart that you don’t need to know with absolute certainty what you want.