“My career path hasn’t been linear, and I don’t think I should expect it to be linear.”
“Continuing to have faith in my own abilities to learn new skills, acquire new knowledge and build things while doing the right things will pay off. It always has”.
This conversation with a senior product leader has stuck with me for a while, where she realized she needed to stop comparing her path to others. This was refreshingly honest about something we all experience but rarely admit: most of us are making it up as we go along.
And its actually brilliant.
The Myth of the Perfect Path
We've been sold an outdated blueprint: that careers should look like climbing a ladder.
College → Degree → Industry Job → Promotions → MBA → Leadership → Retirement.
But here's what's actually happening in the real world: careers look less like ladders and more like jungle gyms. You climb sideways, sometimes down, occasionally you swing from branch to branch, and every now and then you discover a path you never knew existed.
Why Non-Linear is the New Normal
What is changing in the world, that makes the non-linear path to be on the rise.
Here are three shifts that are causing this rewriting of the career playbook:
We're living (and working) longer.
Forget the 40-year career. You're looking at 60+ years of work life.
That's not a ladder, that's a whole adventure park.
People are working past traditional retirement age not just out of necessity, but because meaningful work keeps us alive and kicking.
An engineer dreams of opening a bakery after retirement. A product manager wants to have a Pilates studio. All of this possible in this lifetime, but they may choose to wait a bit before they pivot.
Purpose beats paychecks.
More people are asking "What impact do I want to make?" or “Will I regret not doing this now” instead of "What's the next logical step?".
We're craving work that we find joyful, feeds our souls, not just our bank accounts. At some point we want to have a bigger impact than the weekly release, monthly audit or quarterly earnings for the company.
New roles emerge faster than we can name them.
The roles such as a Podcaster, Content creator, Prompt engineer, AI data engineer didn't exist when I was figuring out my "career path." The roles you'll do in 5 years probably don't exist yet either.
Also, technological advancement has given rise to the gig economy. Digital platforms have made it easier for businesses to find and hire gig workers, while also providing individuals with access to flexible work opportunities and the potential for diverse income streams.
Your "Messy" Path is Actually Perfect
I used to think my background was fairly linear until I really looked at it:
High-School (confused on the path to pick) → computer science → data analytics → consulting → data products → building products → building teams → leadership → writer/coach/consultant/speaker/educator (I keep expanding what’s possible, no longer putting myself in a box - until I can.)
That's not linear, that's a beautiful zigzag when combined with what I’m good at naturally, and now gives me superpowers I never could have planned.
In product management alone, I've met former engineers, teachers, lawyers, journalists, medical professionals, and designers. Each brought something unique that their "traditional" counterparts couldn't offer in building digital products.
Your seemingly random experiences aren't accidents, they're your secret weapons.
How to Make a Non-Linear Career Work for You
1. Know your why.
Don’t chase a role just because it looks shiny. Be honest about what you're solving for. Is it more impact, more money, more time, more growth ? Clarity of purpose makes decisions easier.
2. Accept the detour.
Sometimes you’ll need to take a step back to leap forward. A title drop, a new domain, a contract role, lesser money, working as an apprentice, it is all part of the path. The path of pivoting is hard and will result in many sleepless nights. There is no shortcut, but know that it is equally rewarding.
3. Become a learning expert.
You’re not competing with your past self. You’re building toward your future one. Know your learning style, and invest in it. A pivot often requires gaining new knowledge and skills. Become a student with a beginner mindset. But don’t stay there too long. Some of us get stuck in the land of certifications and more classes.
4. Experiment fearlessly.
Try small tests before making a big leap. Talk to people in the field. Volunteer. Freelance. Build a project. Design tiny experiments, do them, and review the results. Gather data, not just opinions.
5. Find your people.
Don’t do this alone. The non-linear path can be lonely. Career transitions are easier when you surround yourself with others who’ve done it or are doing it too. Find mentors, join communities, connect with others making similar transitions. On the days when you question everything (and you will), these people will remind you that feeling lost is part of the journey.
Simple , not so simple (insert diagram)
A Story of Possibilities
I recently met someone in an AI community who's now consulting with companies on their AI strategy. Brilliant insights, deep expertise, clearly an AI expert. What will surprise you is that four years ago, he was a business analyst who became a product manager. His AI expertise is entirely self-taught over the past few years.
The Impact of AI and What’s Coming Next
Here's the uncomfortable truth: AI is about to shuffle the career deck in ways we can't predict. The average person changes jobs 12-15 times between ages 18-60. That number is about to skyrocket. Many roles will no longer exist.
If you're already comfortable with non-linear paths, you're ahead of the game. While others panic about their carefully planned careers becoming obsolete, you'll be the one asking, "What's next? What can I build next ? What problems can I solve?"
Your comfort with uncertainty is about to become your greatest asset.
Your Imperfect Next Move
Look at where you started.
Look at where you are now.
Think about what you still want to explore.
Maybe it's turning a passion project into a business. Maybe it's teaching, organizing, or serving your community in ways you never had time for before.
We're living in an unprecedented time where you can actually do many different things that matter to you.
Yes, it comes with uncertainty and a price. All good things take time to build - careers, relationships or wealth. But it also comes with possibility.
What's possible for you? That next role, that dream project, that impact you want to make, may seem out of reach today. It might take three years, or five, or ten. But every day you're learning, growing, even when you can't see the path clearly, you’re moving towards it.
Final Thought: This Isn’t About Having It All Figured Out
If your career doesn't follow a straight line, you're not behind. You're not confused. You're not doing it wrong. This is about believing that something else is possible.
Maybe you want to turn a hobby into a career.
Maybe you dream of teaching, writing, building, or starting your own thing.
Maybe your next big role is still 3 years away - but today, you can take one small step in that direction.
The path may not be straight.
But it can still lead exactly where you’re meant to go.
So, what’s your next move?
Not the final destination, just the next inch forward.
Hi, I’m Dipti, and I work with ambitious professionals navigating growth and change. Each week, I share practical insights, personal stories on leadership and intentional living.
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