Recently, a friend suggested that instead of focusing on culture, language, and motorcycles — topics I'm well-versed in — I share my experiences in setting up a life where I seem to wander about willy-nilly globally, working from anywhere.

But I've never seen myself as a lifestyle writer or influencer. I still don't. I find that entire industry unappetising: full of hubris, shysters, and false prophets.

And the specific circumstances that have led to my ability to do this, while having been in part due to conscious decisions I made, are nonetheless very unique. I don't have children, I and my loved ones are all healthy, and I was born into passports with relatively few restrictions (though I still rue the result of Brexit).

Despite that, the thing that really blocks me from thinking I could help other people "break free" from a corporate career trap, is that I have trouble believing I achieved it myself. I floundered my way into my current life, with tons of mistakes along the way, and often question if I'm truly succeeding.

I'm constantly riddled with insecurity. It's a product of both my upbringing and the career I had beforehand. And so my greatest obstacle to breaking free from the corporate career trap is myself. I suspect that in this, I'm not alone.

"Be a doctor. Or at worst, a lawyer."

I was five years old when I remember first disappointing my parents.

Growing up as the first child of an immigrant family, I was, of course, expected to become a doctor. Generally successful, yes, but preferably as a doctor.

Why else, other than to see me succeed as a doctor, would my parents have left their homeland, made an almost impossible journey across continents, cultures, and languages, and brought me from a country in social and economic ruin — post-revolutionary Iran — to a place of wonder and almost limitless possibility, Australia?

If you're an immigrant, or born to immigrant parents, or even if you're from any part of the world in which your parents have experienced economic struggle and done everything they could to give you opportunities, then you can probably relate. Your parents want you or wanted you to go to school, top your class, do all the extracurriculars, get into the best universities, ace your grades, and then get into medical school. Or, at worst, law school. Or whatever the "it" thing is where and when you're from — banking/finance, software engineering, or whatever.

It doesn't end at university, either. Expectations keep rolling in. Get a great job, get a mortgage, produce children, and so on. After the first child, the torch passes to you!

So it was to my parents' great disappointment that when on my fifth birthday I was gifted a toy doctor set, I promptly burst into tears.

"I don't want to be a doctor!" I cried. From that early age, while I had no idea what I wanted to be, I knew that I did not want to be a doctor.

So the first challenge I had in breaking free was that of the expectations of my parents and family. I know they just want for me all the things they had to struggle for — security, shelter, and stability. Those are luxuries for at least half the population of the world.

I also value security and stability. So to cast them to one side and a) not study the "right" things, and b) not pursue a recommended career, seemed like a slap in my parents' faces.

Ironically, I started my career in one that many would consider to be conventional and safe — I was a corporate consultant, working for first Accenture and then Bain & Co. But my parents didn't understand what this was. Maybe I'll get an MBA, they thought, or get a job as an executive in a company later, they mused.

It took a while, but my parents eventually accepted my path. Their main concern? My happiness. For those stressing about convincing your folks that you'll be okay after leaving a corporate job, trust me, you're in good company.

"So, what are you going to do next?"

People standing around a water cooler. Artwork
Standing around the watercooler, avoiding talking about anything personal

The second challenge in breaking free that I faced — multiple times — was the feeling that I needed to meet the expectations of people around me.

When leaving any job, it's natural for people to wonder what you're going to do next. This might be because they care for you as a person and are interested, but quite often it comes from a place of insecurity.

Often, people don't like their jobs, and may yearn for something more. They suspect that anybody leaving has cracked the code and found something better: more money, better conditions, more prestige, or something.

When leaving a consulting firm as a relative junior, specifically, there were four possible expected answers to the question of "So, what's next?":

  1. An MBA from a prestigious school,
  2. Finance, usually buy-side VC or PE,
  3. Joining a top-tier tech firm or a renowned startup, or
  4. Stepping into a management role at an established company.

These days, another accepted answer may be to start your own startup. It depends a little on the geography. But you had better be fairly advanced in it, e.g. have raised a seed round already.

People expect and almost want you to answer with one of those responses. I am probably projecting, but people then want to compare what you're doing next with what they want to be doing next, or expect themselves to be able to do. "Oh, this person is going to some European business school. I'd go to a better one," they might think. Or "Oh, they're joining a small-cap PE fund. VC is really the next wave," maybe. Again, I'm probably definitely projecting. But man, did that question riddle me with insecurity.

Leaving jobs, I was weighed down massively by this invisible chorus of the expectations of my peers. Whatever I was doing, I wanted it to sound cool and interesting. I wanted people not to just to be happy for me, nor even to be impressed, but to be jealous.

My real friends didn't care about my next steps, other than wanting to see me happy. They value me for "me". I see that clearly now.

In one exit interview that etched itself into my memory, a partner told me to "drown out the noise of peer expectations". Funny enough, when I thanked him years later, he didn’t even remember saying it!

As hard as it was to achieve (there are still echoes of expectations in my head), it was great advice.

So I'm doing the same and sharing that advice with you: Drown out the noise of the expectations of your peers, and believe that no matter what happens, you'll keep the only relationships that ever counted — and they'll seem stronger than ever.

And don't worry if you never totally drown it out. We're human.

Escaping the LinkedIn Trap

LinkedIn started out as a simple spot to store an online resume, and a place less awkward than Facebook for connecting with coworkers. Unfortunately, it has evolved into an infernal vanity fair of clout-seeking influencers, posts about "exciting news", and even "learnings" from bad news.

But personally, the worst part is that LinkedIn became another place to feed my insecurities. Just as in Instagram people present a carefully curated cross-section of their lives, showing only the best moments through filters, LinkedIn shows a window only into things when they're going well: Promotions, new jobs, fundraising rounds, and so on.

People don't post about when things go badly. "I hate my job," is the beginning of no post. Nobody says: "Another awful Wednesday," "My boss displays all the hallmarks of narcissistic personality disorder," or "I just got 2/5 on my performance review and will probably be managed out, even though I work my ass off to make my boss look good."

On LinkedIn, the only bad news people post is either not their fault or comes with a silver lining of "learning". E.g. their company downsized, and they know they can feel company in misery. Or they failed to raise a fourth round, and want to tell a story about perseverance.

I can't help but cringe every time I read a post that begins with "I'm excited to announce that..." because it so often seems to be something with thinly-veiled hubris, like "Our third funding round is oversubscribed!", or "I'm HIRING for the position of Junior Senior Executive Vice President Personal Schlepper!" or "I've just accepted a position as a thing-that's-better-than-you!"

If this has been you, I know maybe you are actually excited by those things. You worked hard for them, sure. But it's the egotism that gets to me. What's the point of announcing these things, other than for likes, shares, and subscribes?

Some believe they're networking, and that LinkedIn may help their careers. But, other than entry-level positions, it's very hard to get a good job though LinkedIn. You get decent jobs because you know someone, or get to know someone. I have a good resume. I've applied for dozens of jobs in LinkedIn, in mid management and above. But I've never had any success.

LinkedIn became such a net negative experience that I deactivated my profile (leaving the option open to return, if I need it for some new function). You can read about that here.

After I ditched my "career", deactivated LinkedIn, and broke ties with people weighing me down emotionally, I was surprised by one thing — the people I kept in my life suddenly seemed so much better. They're people I really love having around, around whom I feel no insecurity.

What Will You Do?

If you're sitting at your desk, wondering how you can phone in preparation for a meeting for a presentation that might be cancelled anyway, then you may also be wondering how you can break free.

You might be thinking, as I was, that there's a balance. You don't want to disappoint your teammates, your stock portfolio if you have options, your boss, your colleagues, your family, or the bank that holds your mortgage. Some of those are more important than others!

There are generally three kinds of shackles that we have:

  1. Ones we can't avoid. These are things like money, as not everyone is gifted a relatively good circumstance, or health, either of ourselves or of someone we have to take care of, like parents or a loved one.
  2. Ones we choose for ourselves. These are things like mortgages, children, and lifestyle. Many of us fall into them almost due to sheer life momentum, but they're still choices.
  3. Ones totally in our own heads. These are the expectations of other people, or just of ourselves.

The first two categories present their own complexities, warranting a separate discussion. But hopefully, the above has given you a little to think about when it comes to dismantling thoughts in our own heads — our internal obstacles to breaking free.