Image by Israel Sundseth

Are you stuck in a job that doesn’t suit you? Ready for a career change but have no idea what else you could do – or where to start? Using his own story, Richard explains how overcoming conventional career rules can radically increase your chances of finding something you love.

It was one of the hardest phases of my life.

On the surface, I had a good job at a well-known company. I had been promoted several times. I had a mortgage, traveled for work, and had great prospects ahead of me.

Inside, however, I felt deeply unfulfilled. I didn’t enjoy my work, felt like I wasn’t reaching my full potential, and longed to wake up with the feeling that my work made a difference – for someone or something.

But I had no idea what else I could do.

In fact, I had struggled for years to find a way to change, but without making any progress.

Eventually, as you will read below, I came out on the other side. But it was not an easy journey.

These are the lessons I learned along the way.

What You Need to Know

If you are stuck in your career change, you will encounter three main challenges – or paradoxes.

1. You are the one who wants a change, but you are also your biggest obstacle

In the depths of my despair about my job, there were signals from all sides that I was not in the right place: I was embarrassed to talk about my work at parties; I couldn’t imagine taking over my boss’s job (or that of his boss); and I was terrified of not being proud of the work I had done in my life when I was 60 or 70.

In my daily life, I simply felt numb – unimpressed by the meaningless work I was doing, and seemingly trapped in a “Groundhog Day” reality where I woke up every morning to the same story.

At the same time, however, I had no idea what else I wanted to do (or if I did, no sense of whether those ideas were even feasible) – and no starting point for where to begin.

Looking back, I recognize something today that I wasn’t aware of back then – that I was wearing blinders in my view of the working world. All I knew was the industry I was in. I had superficial insights into a few other professions, but there were so many fields and roles that were completely outside my field of vision.

I was also afraid of a pay cut, afraid of what my family and friends would think, and afraid of losing the status I had worked so hard to achieve.

These were not obstacles in the outside world; they were obstacles within myself. It was me – my lack of knowledge and my fears – that held me back the most.

Does this resonate with you?

2. You don’t figure it out by figuring it out

I was a knowledge worker: paid to think, solve problems, and interact with others.

So why couldn’t I figure out what else I wanted to do?

My first approach was to come home from work, wrap myself in my blankets, and mentally go in circles trying to analyze what else I could do.

I found no answers.

I also read every single book on career change that I could get my hands on, scoured the internet for advice, and took numerous personality tests.

But still no clarity.

The simple truth is: If the solution to your career change lay in more analysis – in making more lists, reading more books, taking more psychometric tests, or just mentally mulling it over – you would have already found it.

3. You don’t find a job by looking for one

When I started looking for something else, recruiters were my natural first point of contact.

They excitedly talked to me about positions at competitors or other roles in smaller organizations.

But all of that left me completely cold.

It was more of the same. I wanted to do something radically different, and they couldn’t help.

Maybe you’ve spent hours scouring job boards or reading job alerts, only to feel even more unhappy because you kept seeing that you lacked the required experience or qualifications. Or you had similar experiences to mine with recruiters. Or you sent your application materials for jobs in other fields, hoping to at least get an initial interview. But nothing.

These are all features of a traditional job market that is not designed for career changers.

Without your fault, you simply won’t be able to compete with others who have experience and skills in the other field that interests you.

What You Need to Do

There are solutions to each paradox, but they are probably not what you think (they weren’t for me at first).

1. Do it with others, not alone

“Alone we can do so little; together we can do so much.” – Helen Keller.

The biggest challenge in my career change was inertia. I wanted to change, but I didn’t want to risk the security of my existing job.

I was comfortably unhappy.

I repeatedly had bursts of energy to do something for my career, followed by phases where I was swept away by ‘life’, only to resurface weeks or months later to find that nothing had changed.

I only really started making progress when I consciously placed others around me.

I began looking for others in my company who also wanted to break out; I hired not one but two career coaches; and I started meeting and spending time with different types of people (one of whom would eventually lead me to a job I loved – more on that below).

The overall effect was new ideas, different contacts, and accountability – all of which ultimately led to progress.

Think of your career change as an expedition, not a day trip.

If you were to climb to the base camp of Mount Everest, you might be able to do it alone, but most likely you would want to go with others – like-minded people, a guide, a support team. It makes the journey safer, faster, and, damn, a lot more fun.

2. Act, don’t just analyze

“Ideas emerge when different worlds collide.” – Seth Godin.

On my path to a career change, it took me four and a half years to exit a career that didn’t suit me.

For most of that time, I was stuck in analysis paralysis.

As the coach I was working with at the time said: “Richard, it’s like you’re standing in a forest and have several paths in front of you. But you’re paralyzed because you don’t want to make a mistake. And the challenge is: If you don’t take any of the paths, you’ll never get out of the forest. If you take one, it might not be the right one, but you can correct it.”

When I started to act instead of analyze, things began to change.

Here are some of the things I did.

I enrolled in a part-time journalism course. I loved it, but it quickly became clear that it shouldn’t be my career.

I shadowed my friend who worked in PR for half a day. I did the same with a friend who worked as a Japan-yen bond trader at an investment bank. Both fascinating worlds, but neither drew me in.

Notice what I did, though.

As Seth Godin describes, I entered different worlds – sparked ideas while simultaneously crossing opportunities off the list instead of leaving them as open questions in my head.

I also tested ideas in a way that allowed me not to give up my main job before I figured out what I really wanted to do (more on how to do that in our Lean Career Change approach).

Eventually, thanks to an introduction from my future sister-in-law Sarah, I entered the offices of a social startup – and knew within minutes that I had found something that absolutely suited me.

If I had only seen the organization’s website or a job ad in a newspaper, I might never have discovered the connection I had with them. But it became real by meeting the team, seeing the environment, and feeling the energy of the place.

In short: Action precedes clarity, not the other way around.

3. Look for people, not jobs

“Opportunities don’t float around like clouds in the sky. They’re attached to people. When you’re looking for an opportunity, you’re actually looking for a person.” – Ben Casnocha.

Job boards, recruiters, resumes, and Google all have their place in a career change. But they are not where to start.

Instead, focus on connecting with people.

The strength of standing in front of people is that you can present the whole you – something a resume simply cannot do.

I’m an introvert. So you won’t find me exuberantly at a networking event. But I feel comfortable meeting people one-on-one or having phone calls.

That’s exactly what I did – with a whole range of people whose roles interested me.

It took time, there were many ‘dead ends’, but ultimately it led me to a role in a field I didn’t even know existed before.

Moreover, this approach meant I avoided the ruthless filtering that takes place in conventional job applications.

I wasn’t ‘qualified’ to work at the social startup I had fallen in love with. But what I had was plenty of enthusiasm and a willingness to learn. That would never have come across in my resume.

I didn’t get the job there through a formal application. I got it because I built relationships with people in the organization. I did some pro-bono work that led to consulting work, which in turn led to an interview for a full-time position.

Oh, and if you’re interested: I had the worst interview of my life for that position. I wanted the job so badly that my brain froze, I stumbled through the questions, and left thinking I had messed it all up. Catastrophic. Or it could have been catastrophic if this had been my first contact with the team. But it wasn’t, and thanks to the strength of the relationships I had built, I got the job anyway.

Remember: People first, jobs second.

What Your Next Steps Should Be

“To know and not to act is not to know.” – Buddhist proverb.

A career change is not easy – otherwise, everyone would do it.

There are hundreds of stories here in our success stories section and elsewhere that show it is possible.

And remember, this is not just about your career; it’s about your life.

It’s about how you feel every morning; how that affects your health and your relationships; and ultimately, what impact you can have on the world by being alive in what you do.

The stakes are high.

But they are even higher if you do nothing.

So for heaven’s sake, don’t just read this article. Do something about it. Please.

And let me know how it goes.

What have you learned? What steps will you take? Share your thoughts in the comments below.