What I learnt from all the layoffs in my “unconventional” career

Let’s face it, 2023 hasn’t been the smoothest ride. Layoffs, reorganisations, bankruptcy and uncertainty seem to be the theme song for many careers. If you’re one of the unlucky ones — I hear you, loud and clear.

If you are struggling, let me share my story. I hope it can spark a flicker of hope and empower you to bounce back like a boss!

I won’t sugarcoat it — my journey wasn’t a walk in the park. But amidst the setbacks, I discovered a resilience I never knew I possessed. And you know what? That resilience became my superpower.

Since I was a kid, the expectations were clear for me: go to a top school, get a stable job, become a doctor or a lawyer, get married, have kids, stop working and take care of the kids.

Growing up as a daughter in an Asian family, anything else often felt like a deviation, a gamble into the unknown.

Yet, here I stand, an entrepreneur navigating the exhilarating and often nerve-wracking world of tech, with a completely unrelated background!

I graduated from a top global institution with a Biochemistry degree, but can you imagine just 2 years after stepping into the tech world I start having trouble keeping up with my finances and lived off free food and drinks at WeWork events?

I’ve always been a top sales person at tech firms, in VR, AR, AI, machine learning, digital products and way more. Though I was terribly wrong to assume that just because I am capable I will not face any trouble in my career or life.

Being laid off a few times, didn’t manage to get paid for over 6 months and so much more. All happened within a year. That’s only when I realised it’s a wakeup call, stability is a luxury and myth.

Shortly after all the layoffs was the birth of my company DigitSense. My journey in becoming an entrepreneur and starting a company alone has taught me way more than before.

I am now 4 years into my entrepreneurial journey, finding more companies, merged with other startups, launching new businesses bootstrapped. This journey hasn’t been easy, but looking back, the lessons learned are invaluable.

1. Ditching the comfort zone: safety nets don’t guarantee smooth landings.

I worked for a well funded startup just before I was laid off for the first time, they were already at Series C, with a seasoned founder with a great track record. I felt like I’ve done all the due diligence possible. Who knows none of these were guarantees.

While a steady paycheque feels reassuring, it breeds a false sense of security.

The tech industry, like many others, is prone to turbulence. Remember the dot-com bubble? Relying solely on a job, no matter how stable it seems, leaves you vulnerable to external forces.

Embrace continuous learning, build diverse skillsets, and explore options. After all, the next layoff might not be a “them” problem, but a “you” problem if you haven’t prepared.

Hence I always repeat myself: It’s not your fault that your employer fired you, it’s your fault for not having a second stream of income.

2. Defying the norm: success doesn’t have a one-size-fits-all label.

Society loves its well-worn paths, often judging anything off the beaten track as “unrealistic” or “risky.” But remember, the 99% aren’t always right. What works for them might not resonate with your aspirations. Trust your instincts, research, and experiment. Every individual has their own unique “theory of life,” shaped by upbringing and experiences. A “no” from others doesn’t define your potential.

Same as how Ramit Sethi says: What’s your rich life?

Success and wealth comes in all forms — money, freedom, independence, assurance, security and sense of accomplishment.

Don’t try and copy other’s life.

Don’t blindly follow the expectations that others set for you. They might not be able to see what you see.

3. Seek mentorship, but with discernment.

Advice is readily available, but be critical about what you hear. Don’t blindly accept every suggestion. Before taking someone’s word as gospel, evaluate their experiences and qualifications.

Don’t let professors tell you how to run your business when they’ve never started one themselves.

Just like you wouldn’t ask someone who’s never been a mother for advice being one right?

Seek guidance from those who have walked similar paths and understand the specific challenges you face. Seek advice from those who have failed enough to know what not to do.

4. Imposter syndrome? More like imposter myth.

Self-doubt is normal, but in entrepreneurship, it can be particularly crippling. The fear of inadequacy, the feeling of “not belonging,” often manifests as “imposter syndrome.”

Here’s the truth: that syndrome doesn’t exist until you you learn how to spell it.

It’s a self-fulfilling prophecy fuelled by negative self-talk. Instead, reframe the narrative. Focus on your achievements, your skills, and your unwavering determination.

Remember, every successful entrepreneur started somewhere, feeling just as unsure as you might feel now.

5. Nobody is irreplaceable. Find your value.

Employers or employees, we are all replaceable. Question is, to what extent are we.

Possessing the knowledge, experience and wisdom that others cannot makes you an invaluable candidate, in the job market or the commercial world.

Instead of carrying competitor analysis on your products only, do the same on yourself as a founder or as an employee — what makes you the most competitive in the market.

6. Build relationships, not contacts

You never know who would be of help when you have a career change. What do you think possess a better chance when you go job hunting, knowing the CEO and having him/her reach headhunt you directly? Or sending your CV to 30 employers.

In my industry, fundraising takes time, especially for early stage founders. Investors invest in you, not the product or the business. They trust that you’re the right person to execute it.

Think about it, if that’s the case, doesn’t trust take time to build?

Good investors and partners are not a cold email away. Try asking for advice from people, instead of asking for a favour directly. You might end up with a better offer.

7. Learning starts only after school

Learning is lifelong. When I was still a fresh graduate years ago, I’ve once got a friend who graduated with a Master in Engineering from University of Oxford, as well as multiple other Ivy League graduates who complained how they ended up with the same job with the same pay from those who didn’t even get decent grades from a decent institution.

The certificate is only to prove that you didn’t quit within the 4 years.

Though as I said above — find something that makes you invaluable. Imagine how many graduates there are from top 50 global institutions every year. Talents are everywhere, just because you have a good degree from a top institution doesn’t mean you’re smarter necessarily.

The world is constantly evolving. Stay curious, keep learning new skills, and adapt to emerging trends.

Just because things were working fine doesn’t mean it will. Always keep an eye out for the waves.

You either sink, swim, or surf with the waves.

My journey is far from over, but I hope my learnings would provide you value. As an “unconventional” entrepreneur, I encourage you to break free from societal expectations, embrace calculated risks, and forge your own path to success.

Remember, the greatest innovations often emerge from those who dare to defy the norm. What’s your unconventional story waiting to be told?

What are your thoughts? I’d love to hear more! Feel free to reach out to me via LinkedIn or Twitter for shorter tips on how to craft the next viral product.

Moon is the Founder & CEO of DigitSense, a digital product studio that designs, develops, and markets digital products like a tech startup on its own, where we blend cutting-edge tech with user-centric magic to transform your vision into reality.