The other day, I was reading this story:
It was about a 31-year old guy working in software. In short, he was earning really good money, but hated it.
(He’d already changed companies three times, and realized the company wasn’t the problem, it was the job).
But…
As he was planning to marry his girlfriend, he wasn’t sure if killing the cash-cow was the right move.
So, should he just tough it out in software?
Or move on to greener (but perhaps less lucrative) pastures?
It’s a tough decision.
And although I’m not in the same boat, I know what I’d try to do if I were him: instead of throwing caution to the wind and making big moves, I’d use my “low-risk, high-reward” strategy for career switching.
Here’s the nuts and bolts:
🐒 Monkey-branch, don’t monkey-jump
If you’ve ever watched monkeys in the wild (or on Youtube), you’ll notice that monkeys rarely jump through mid-air to get from one tree to another.
Instead, they use vines and branches between trees so they’re always grabbing onto something with at least one limb. It’s far less risky that way.
I.e they “monkey-branch”.
I like doing something similar with careers, too.
The career equivalent to “jumping” would be switching roles AND your industry at the same time. (Risky!)
Whereas a much safer approach is to change industries OR roles, but not both at the same time.
Let’s say you’re in sales but want to move into medical administration. A good stepping stone or “branch” would be medical sales. This will help you get to grips with terminology and equipment, plus connect you with potential employers as you do so. When you’re in, you’ll find it much easier to then “monkey-branch” again into medical admin.
Another example:
You're stuck in finance but love the idea of coding. Don't throw away your career in finance just yet. Instead, look for opportunities within your current role. For example, try to introduce automation into your job by writing a script. You’ll get to ‘code’ in a professional sense.
An ex-colleague of mine did just that.
The project was challenging, but it gave him legitimate coding experience which he later used to transition into a programming role.
🌌 Get unconventional experience
There’s one big barrier and one big risk when changing careers.
The barrier: no experience.
The risk: what if it doesn’t work out? (out of the frying pan and into the fire)
A nifty way around both is "unconventional experience" – find a startup or nonprofit to work for in your spare time while keeping your day job.
A friend landed her dream job doing this. She did social media for a startup for three months on nights and weekends, then got recruited for a full-time remote job once she brought results.
Another example: Want to be a data scientist with zero experience? Either:
- Contact some startups and suggest 3 projects you can help them with for a few months.
- Sign up on Fiverr or Upwork for small projects at entry-level rates (your goal's not money, just real experience).
You don't need something revolutionary. Just something with impact you can discuss in interviews.
Plus, you’ll also figure out if you REALLY like doing the job in a professional setting (the hard truth: most people want to change careers just because they hate their current jobs/roles, and not because they love the career they’re trying to change into. Which is a big problem). More on this next.
⚠️ PSA: Hold up – is it really what you want?
Most careers look different from the inside than they do from the outside. Before making a move, understand what you're actually signing up for.
The UX designer job isn't just creating beautiful interfaces. It's endless feedback loops, stakeholder meetings, and documentation. Programming is more debugging than building cool features. Content creation is 80% promotion, 20% creation.
Make sure you love the actual work, not just the idea of it. Those mini-projects and side hustles let you experience the unglamorous parts before committing. If you enjoy it when there's a real deadline and actual stakes, that's a good sign.
Second, consider how AI might transform the field you want to enter. Graphic design, content writing, and even entry-level programming are already being transformed. The jobs won't disappear, but they might look very different by the time you're established in the field. The graphic designer of 2026 may be more of an AI-prompt engineer and creative director than someone who manually creates every asset. Make sure you're learning skills that complement AI rather than compete with it.
The key question isn't "can I do this job?" but "will I still want to do this job after six months of the unglamorous parts?" Be honest with yourself about that before making any big moves.
〰️ Side hustle
You often don’t even need to get permission to try out the career you want. You can just start doing it yourself.
For example:
If you want to get into content creation, you don’t need to get a formal job as a content creator. Just start creating your own YouTube content as a side hustle. Don’t wait for a company to give you permission to do the job you want to do — just do it.
Some more examples:
- Want to be a programmer? Build your own mini website or app for a simple idea you want to build.
- Passionate about fitness? Offer to create workout ideas for friends and their friends. Then, charge for more detailed variations.
- Aspiring to be a writer? Begin by writing short stories or articles and publish them on a blog, social media or even self-publish the e-book on Amazon.
Essentially, start your own side-hustle in the industry/role you want to join. That way, you’ll get real experience that you can put on your resume and talk about in interviews.
What’s more? If your side-hustle picks up steam, you might be able to monetize it too.
Back in the day, without the internet, it was DIFFERENT. You needed permission to do stuff because you couldn’t get access to an audience without going through the gatekeepers (i.e. radio channels, publishing sites, newspapers). Now, you don’t!
📱 Rebrand yourself (it's easier than you think)
Your professional identity is mainly in your own head. That "marketing guy" or "operations person" label feels permanent to you, but it's pretty fluid to everyone else.
I've seen people completely reinvent themselves professionally by simply acting as if they were already in their new field. They updated their LinkedIn profiles, started sharing different content, and talked about different projects. No big announcements, just a gradual shift in how they showed up.
The barriers to reinvention are often self-imposed. You can start becoming your next professional self today by simply changing how you talk about your work — starting with your LinkedIn profile.
Speaking of LinkedIn —
I kept seeing friends with amazing experience get zero messages on LinkedIn while others got flooded with opportunities. The difference wasn't their experience - it was how they optimized their profiles.
We built a free tool that shows you exactly how to optimize yours — with AI features that will rewrite your profile so it’s tailored to your target industry. Takes 30 seconds:
📝 Create content
A similar smart approach is to start creating content in the area you want to move into. This could be a blog, LinkedIn content, or a daily/weekly newsletter, or a dedicated Twitter (or “X”) account.
My buddy Bryan did exactly this.
He was in tech but he wanted to become an investor/venture capitalist. He didn’t have an MBA or conventional business experience, which was a requirement for most of these jobs.
So he started researching companies and writing about whether or not he thought they were good investments on Twitter. He used his content to build strong relationships in the VC world, position himself as someone who knows what he’s talking about, and a year later he got hired by a VC.
(Funny enough, HE QUIT the new job just 9 months later. Turns out a lot of the VC job was just creating Excels and PowerPoints for his manager and was far from glamorous. This is also why I insist you really ‘test’ out a field first and speak to people in the industry before doing so much to break into it).
