The career ladder is a lie. Why the best careers zigzag

Did you set a resolution to get a promotion in 2024? You certainly wouldn’t be alone in beginning this year with the worthy goal of moving up another rung on the career ladder. But don’t be fooled into believing the myth that a successful career trajectory always consists of a vertical line.

Of course, plenty of successful people know that it’s often difficult to build a successful career by mapping out a straight line. “You can’t connect the dots looking forward,” Steve Jobs told Stanford graduates in his 2005 commencement address. “You can only connect them looking backwards. So, you have to trust that the dots will somehow connect in your future.”

For many, their rise involves bold moves into new areas. It takes courage to build such a career without necessarily knowing where it will lead. I know this for a fact, because my career was built by plunging into vistas that I never could have imagined. I’m suggesting you may want to do the same.

EARLY CAREER

It’s sensible to begin your career by building on the education and training you received. Most of us start out using the skills we gained in university or in another educational program. That’s your strength, and it will likely shape your first job.

I got an advanced degree in English lit and took a teaching position at York University in Toronto. It was exciting at first, but after eight years, I hit a wall. I lost the directorship of a writing program I had developed and so I decided to split from the academic world.

Emily He, former SVP of human capital management at Oracle, says that such job changes are frequent among young workers. “Today’s college graduates will have a dozen or more jobs by the time they hit their 30s” she says. “Your 20s are used as the time where you actually figure out what you want to do.”

FINDING A BETTER FIT

Ideally, at some point you’ll find an area that excites and inspires you. I turned to the business world, knowing little about business but thinking there must be many people who need the sort of communications training I had taught at the university.  

It takes tons of strength to break free from the career trajectory you may at first have envisioned. And it takes guts to start networking for a job outside the sphere to which you are accustomed. But I did it because I saw opportunities in this new context. Every failure can lead to something better if you believe in yourself.

I cold called the head of HR for a big tech company in Canada, and amazingly I got him on the phone, I pitched him, and he set me up with an interview with an SVP. Networking in a new area is important, and you can’t be shy if you want to break into new territory. I had the interview, got the job, and was paid five times what I’d gotten at the university. Zigzagging, I discovered, can also be lucrative.

BUILDING A NEW SKILL SET

My years in business were as valuable an education as my time as an undergraduate and graduate, and provided new perspectives that led to new ideas about where I might go next.

I brought a communications background, and my new boss taught me how to prepare speeches. He became a valuable mentor. It’s important to remember that leaders are anxious to “upskill” people they feel are suitable candidates for a role.

My new job consisted of writing speeches for the CEO, and during the next eight years I worked as a speechwriter in four companies. I learned about the mindset of the business community and the challenges executives faced. I discovered that many C-level executives wanted my help with their speeches. Not all of them had the luxury of a dedicated speechwriter. I saw an entrepreneurial opportunity.

During my last three years as an employee, I planned the firm I would launch. When I was ready with a plan, I zigzagged to this still bigger opportunity: entrepreneurship.

BUILDING A COMPANY

When you have a big idea, and you’ve planned it well, all that’s left is to go for it. After piloting the concept with a few courses (while still employed), I launched The Humphrey Group, to provide executive communications training to my former C-Suite colleagues and other C-level leaders. I was 42.

I had never seen myself as an entrepreneur, but that’s what zigzagging does: it gives you new perspectives on yourself. It allows you to build a career you never could have dreamed of. My business was successful from the start. The executives I had known from my last job became my first clients, and they told their friends about the training, and that was the beginning of our success.

I made up the rules as I went on. Don’t worry that in your new role everything seems unfamiliar. That’s what happens when you zigzag to new heights. I led The Humphrey Group for close to 35 years, and we had a global business and dealt with many of the Fortune 500 companies. Now my son heads the company. The beauty of zigzagging is that you cannot possibly plan a career that will be as fulfilling as the one you create in this non-linear way.