Reconcile Your Personal-Professional Divide

After my business collapsed and I got through the worst months of my identity crisis, I started looking for a new job for the first time in ~8 years.

My first interviews... weren't exactly a success:

I was putting on the mask of a "Professional job candidate applying for the project/product manager position at Company".

Kinda like...

Yet I couldn't relate to this "professional" self of mine personally.

Martin the Individual is the opposite of serious and pretentious. Like, I wear a mohawk, red track pants, and a yellow bomber jacket, for Pete's sake. Colors are great!

Naturally, trying to act like someone I wasn't made me seem pretty fake.

Ever noticed yourself doing it as an employee or an entrepreneur? Do you put on a mask when you're at work? During interviews? When publishing on LinkedIn? When writing about your business? Talking to customers? Investors?

Are you actually being yourself in professional environments? To what extent?

I started my professional journey as myself, then turned into a complete pretender, then had to struggle to find my way back to being comfortable being myself again.

I call this scaling my personal-professional divide.

Separating professional from personal

How did I get here in the first place?

Back in ~2011, I was just a developer annoyed by software. The blog I had started back then was personal and professional: I was Martin the Guy (personal) ranting about things like Magento errors and GIMP UX (professional-ish).

I had no particular reason to filter my thoughts back then, so I simply shared what I had on my mind. My writing had my personality, even if that personality was a little rough around the edges:

Still, I was being myself personally and professionally. No divide in sight yet.

About a year later, one of my business ideas failed and left me with some code that I turned into a product, and eventually into a new business. My blog had an audience by that point, so I decided to repurpose it into my business website.

For a while, I still published as myself. But the more serious I got about my business, the more "serious" my writing became. In my new world, "business" had to mean "serious". Slowly, my personality faded away from my writing.

And eventually, Martin became Martin Boss, Founder & CEO.

This didn't just affect my writing. I started exhibiting this "split personality" when talking to customers, to my team, and to people in real life. I started putting on the mask of a "Founder & CEO" whenever I felt like I couldn't just "be myself".

What was that mask like?

It was "serious and confident", for the most part. I knew that I didn't exactly know what I was doing as an entrepreneur, but I couldn't admit this to anyone, even to myself sometimes. So I had to pretend I got everything under control. I tried faking it. I even bought a suit to "look like a CEO".

By the time I started publishing on LinkedIn a few years later, "Martin Boss, Founder & CEO" was a full-blown separate persona that had little in common with Martin the Guy:

• Martin the Guy was an introverted developer turned entrepreneur.
• Martin the CEO was an expert on two-sided marketplaces. He was eager to connect with the people in the industry. He wore a suit. He projected expertise.

This posed a couple problems:

First, Martin the CEO was boring. And kinda pretentious. And silly.

Imagine stumbling upon an unexciting post in your LinkedIn feed written by a cookie-cutter "CEO" of a completely unknown company. How do you feel about it?

If I had to guess, it's be a mix of "yawn", "meh", "who cares", and "dude, you're full of shit". Unfollow, I don't want to see this.

I got somewhat better at LinkedIn'ing over time, but I still wasn't being myself.

Interestingly enough, I wasn't active on Twitter for this same reason:

• LinkedIn was professional. Martin the CEO, no matter how dry, could still publish articles on marketplace software and attract followers.
• Instagram was personal. Martin the Guy felt comfortable being a somewhat more polished version of himself just for his friends.
• Twitter was neither. Purely professional content was too boring for Twitter, and purely personal content wasn't a great fit either. Besides, none of my friends used Twitter anyway, and I had Instagram for this stuff.

So, I briefly fluctuated between being the CEO and the Guy on Twitter, and then abandoned it altogether. It took me reconciling my personal-professional divide to finally "get" Twitter. (Pro tip: Twitter is personal AND professional).

Second, Martin the CEO was too far removed from Martin the Guy.

I now had a team of people working for me, but I still little idea what I was doing. And I was too afraid to ask. So to keep the CEO persona going, I had to double down on it.

Pretending to be someone you're not is easier if you stick to writing, more difficult on calls and video, and almost impossible in real life, unless you're good at pretending.

I wasn't, so I had to stick to writing. Whenever I had to call people, record videos, or meet in person, I felt totally out of my element. Cringe.

Third, and most crucially, pretending I was Martin the CEO made me sweep my own (and my business's) weaknesses under the rug.

Why talk to customers if I can write an article about the importance of doing it? Why work on improving my people skills if I can find workarounds? Why deal with our lack of vision and strategy if I can pretend I know what I'm doing 'til I make it?

This couldn't last forever.

I knew it's a massive problem, but I didn't know how to fix it. It was a psychological issue not a business one:

• Dropping my professional persona would mean I've failed as the Founder & CEO, wasting years of my life looking for workarounds to fundamental issues.
• But bringing my personal and professional selves closer together just wasn't something I was capable of at this point. The gap was simply too large.

Such a classic sunk cost fallacy. This lasted for a few more years.

Unfortunately, the business was doing just good enough not to collapse outright, but not nearly good enough to be worth it. It was like one of those "too good to leave, too bad to stay" relationships, except that it wasn't even "good".

Fortunately, I did eventually make a few more dumb business decisions that put me and the business out of our misery.

It did come crashing down a few years too late, together with my whole identity.

Martin Boss, Founder & CEO, was no more.

Getting my two selves back together

I consider myself lucky it all worked out the way it did.

The identity crisis and the resulting depression was ugly and I wasn't sure I'll make it, but I managed to find help, get through it, and get rid of my useless professional persona. This eventually helped me get a great product manager job.

But I was careful not to simply put on another mask and end up with Martin the Guy and Martin the Product Manager. From that point on, I started putting a lot more effort into being just "Martin, who's into PM in addition to a myriad other things".

I finally felt whole for the first time in years.

Now, my case was somewhat extreme. If you're struggling with reconciling your personal and professional, you probably don't need to go through everything I've gone through, identity loss and everything.

Here's a simpler way to bridge your personal-professional gap:

1. Find a sensible middle ground between your personal and professional selves.
2. Tweak your professional self to get it closer to that middle ground.
3. Work on your personal self to get it closer to that middle ground.

Simple!

Here's what the process looked like for me:

First, I found a sensible new middle ground.

My personal self was a slightly socially awkward developer turned small-time founder, while my professional self was nothing short of Jeff Bezos.

Clearly irreconcilable. You can't fake THAT 'til you make it.

To find a new middle ground, I outlined my strengths that I could double down on and my weaknesses that I could work on. It might have looked somewhat like this:

My strengths:

• Generalism
• Curiosity
• Quirkiness
• Friendliness
• Entrepreneurial and technical experience (product, management, software)

My weaknesses:

• Lack of specialism (generalism is a blessing and a curse)
• Slight social awkwardness and sensitivity to criticism
• Lack of deep analytical and strategic thinking skills
• Lack of experience working in professional environments

Clearly not Steve Jobs material, but not exactly a nobody.

I enjoyed building products, and I could be a decent manager. After all, I had experience leading teams of my own developers and designers, even if small, and having fun with it. Going back to engineering was the last thing I wanted.

However, I also realized that my lacking social and analytical skills were one of the reasons my business wasn't exactly a success. It made no sense to try acting as a high-powered CEO when I clearly wasn't one.

But these were the weaknesses I was ready to admit and to work on.

The new middle ground ended up being something along the lines of "Martin is a friendly, open-minded, and slightly quirky engineer-turned-founder-turned-PM with a wide range of skills and experiences and eager to keep improving."

Double down on strengths, address the weaknesses.

Next, I tweaked my professional self.

This was the easy part. I stopped trying to "go big or go home" in business, and instead kicked it down a few notches to aim for something more realistic.

Instead of getting obsessed with Steve Jobs and Elon Musk, I started getting inspired by brilliant product managers, skillful founders, and energetic entrepreneurs running small and medium businesses.

This instantly made my experience and my challenges a lot more relatable.

Finally, I started working on my weaknesses.

That was the hard part. Still is.

You don't become a strategic thinker overnight. You don't become immune to criticism overnight. And you sure as hell don't get to resolve your psychological issues overnight when they've been piling up for years.

But that's the only way to fake it 'til you make it.

I still get to experience that gap occasionally.

Sometimes, I catch myself writing or saying things that sound... just a little too professional for my liking. Sometimes I sound like I'm trying to impress someone by being professional. By being an "experienced product manager".

But I feel like I've become pretty good at catching myself in these moments. And instead of asking myself "What would Steve Jobs do?", I try to ask myself "What would Martin do?"

And that helps bring my personal and professional closer together again.