Changing Careers: Where to Start?

Look at the past, the present, and the future.

Found yourself stuck in a job you hate, or without one?

Changing careers won't be the first option you'll consider, but let's say you've come to this point. What next?

These are the thoughts I've shared with a good friend who's been stuck at a crossroads in their professional life.

I'm in product management today, but it was never my plan from the start.

A decade and some ago, I got my Bachelor's of Science in Computer Science and started working as a software developer. It didn't take me long to realize I'm not enjoying it, so I left for freelance, and then went into product businesses.

By the time I had to wind down my last business, I hadn't written code for at least a couple years. I had to start looking for a new job, and engineering wasn't it.

To be able to figure out what to do next, I had to answer a few questions:

  • What's my story, and what can I do?
  • Who am I today, and what do I feel like doing?
  • Where am I heading, and where do I want to be?

Here's how I looked at this:

The Past You. What can you do?

As much as I'd like to start with "what do I want to do?", I had to be realistic about my prospects. So I started with "what can I do?"

On one hand, I had a bachelor's degree in Computer Science, a few periods of employment in my specialty, as well as years of freelance and entrepreneurship behind my belt.

On the other hand, I had just wound down the business I'd spent years trying to grow, and I was pretty much broke, and thoroughly burned out. It wasn't some great success I could proudly show off.

Not great, but not exactly terrible. I knew people with less experience and less education starting their new careers from the ground up, and I was absolutely in a better position.

My first answer to "what can I do?" was "a lot of IT-adjacent things". In addition to my education, career, and business, I've spent years working in Linux environments, configuring servers and home networks, and other technical things.

My second answer was "some sales and marketing-related things". I wouldn't call myself a marketing person, and I wasn't great at doing sales, but I had to do both while running my business, and I was ready to do it as part of my next job if I had to.

My third answer was "managing people and projects". Even if I failed to grow my business into the next Amazon, we've had a good run, and I actually enjoyed it. No MBAs, but quite a bit of real-life experience.

Thinking about these answers made me believe that project or product management careers were the ones that fit me the best. But I was aware of my position, too, and was ready to consider the alternatives.

Sure, I wouldn't make for a great software developer, devops, QA person, or technical support, but I'd be an alright one. And I definitely wouldn't be a great marketer or a sales guy out of the gate, but I had some experience I could rely on.

I did realize I might hate these jobs, and hate myself for ending up in this position, but I also knew these were gratuitous thoughts. I wasn't starting from "rags", and that was a privilege already.

It took me about a week of thinking to narrow down my potential career choices to:

  • Technical IT (software development, devops, QA, support and the likes)
  • Sales & Marketing (including SEO, content, etc.)
  • Management (project, product)

Now, this question will be more difficult to answer when you don't have any relevant experience or education, but it's not just about these two things.

It's still important to consider what you can do before thinking about what you want to do. In addition to your experience and education, think about your skills, character traits, and anything else you could bring to the table.

When you're done with the past, you can look at the present you.

The Present You. What do you want to do?

If the first step was to figure out what you can do, the second step is to figure out what you actually feel like doing in your next job or career.

Think about the following things:

  • What makes you excited, and what makes you bored?
  • What aligns with your identity, and what goes against it?
  • What would you like to do, and what would you hate to do?

In my case, I was using these questions to narrow down my search. It doesn't always have to be this way. You can use these questions to complement the answers you've found during the first step, but it's easier if these two steps align.

This step is important, but it won't necessarily be your top priority. We don't always get to choose what we do. It's great to find a job that aligns with your desires, but if you're desperate this part won't matter that much.

Still, it's good to know yourself, and it's good to know what makes you excited. This can help you pick the better out of a few crappy options, and keep pursuing a better path in the long run, while staying on a worse one in the short term.

Here's what my answers to this question looked like.

What makes me excited and aligns with my current identity:

  • Building things, creating something of value, making the world a better place.
  • Working with and around people, and learning to be more social in the process.
  • New and different challenges, not knowing what tomorrow brings.

What makes me bored, doesn't align with my current identity:

  • Writing code, spending my time around computers instead of people.
  • Specializing, going deep instead of going broad.
  • Predictability, certainty, repetitiveness.

Still, I considered all possibilities.

A Junior Devops, a Web Developer, or a Tech Support position wouldn't make me happy, but it was a better option than staying unemployed or doing manual labor.

Next, it's good to put it into perspective and figure out where you would like to be.

Now that you're done with the present, it's time to look at the future you.

The Future You. Where do you want to be?

"Where do you see yourself in 5 years?"

It's a cheesy question, but it's an important one. Understanding where you want to be 5 years from now makes it easier to make a better decision today.

Besides, it's what HRs will ask you anyway. Why not take some time and answer it?

Here are a few additional questions I've asked myself while thinking about this:

  • Who do I want to become? Who are the people I wish I was? What makes them special? What skills do I lack?
  • Which job can help me be more like those I look up to? If all goes well, how far up can I do? What's the best possible scenario for me if I take a certain job?
  • And what are the negative scenarios? What if I don't get this job? What if I do, and it doesn't work out as expected? Where will I be then five years from now?

This sounds banal, but I feel like so many people don't give these questions enough thought. Your choices today don't just affect you tomorrow, they affect you for the rest of your life.

In my experience, people often fall into one of the two buckets when thinking about the future themselves in relation to their current or prospective jobs:

First, not thinking about the future at all.

I've known people working dead-end jobs and being unhappy, but not doing anything to change this. "It's just the way I am, I won't find anything better."

I've also known people working low-paying jobs they liked who were constantly short on cash and stressed out, but still sticking with it and persevering.

Liking what you're doing is great, but if you're living hand to mouth today, what does the future hold for you tomorrow?

Second, being unrealistic about the future.

It's usually either "the sky's the limit" or "I'll figure something out as I go". I was guilty of this in my early entrepreneurship days. "If only I start this business, get X customers, build this feature, then I'll basically be the next Jeff Bezos eventually".

That's not how it works. You need to be realistic about your prospects. If you don't have a college degree, you'll have a harder time climbing certain career ladders. If you're a socially awkward nerd, you'll have a harder time building a six-figure business.

You might not like this, but being honest with yourself about these questions grounds you in reality. Not having a degree or certain skills isn't a major problem, but it is a major problem if you disregard it altogether.

I was a socially awkward nerd who managed to become good at dealing with people (and loved it) after almost a decade of trial and error. But I'm also lucky it happened this way because I spent way too long deceiving myself.

Be honest with yourself about your present and your future, and you'll save yourself a lot of time and effort.

This isn't a comprehensive career change guide, but answering these three questions helped me narrow down my choices when I was at a major crossroads in life.

It's how I ended up in product management after a decade of freelance, self-employment, and entrepreneurship, and it turned out to be exactly what I needed.

I hope my experience helps you get unstuck, or at least gives you a fresh perspective when considering a new job or a complete career change.