I started my career in 2012, in India, right around the time “start-ups” were becoming both a hype and an attractive alternative to the giant corporations lapping up students through campus placements. A few young and dumb like me realised that startups could probably offer jobs we would enjoy.

“Find a job you enjoy doing, and you will never have to work a day in your life.”
― Mark Twain

Yeah right!

Over the next 13 years, I would build a career in the tech industry, from garage startups to household brands, from India to Singapore. I’ve been around the block, had two careers, been an individual contributor and a manager, been over-the-top happy and satisfied, and been jaded and disillusioned. It is with that experience and perspective that I write the following. I’m not here to advocate one path over another, but rather to reflect on my own journey—one that many of us have experienced in different ways.

I wanted to approach this topic through the lens of skill—one of the few aspects of our careers that offers a somewhat objective measure of growth. Factors like financial stability, creative freedom, and impact vary based on the company, the team, and sheer luck. But skills? Those define how we navigate and shape our careers, no matter the setting.

So, let’s get into it.

The full-time path and skill sets that dictate your growth journey

With the assumption that we are all trying to grow our careers and climb up the proverbial ladder, certain skill sets can give us an edge, whether we’re working at a sleek startup or a structured corporate behemoth. At the end of the day they are all for-profit companies and it’s just a matter of culture that separates the corporates from the start-ups.

Soft skills

Irrespective of what we’ve been promised will deliver us success in our careers - education, intelligence, hard work - the real game-changer is soft skills. Looking back, I’ve rarely been the smartest person in the room, nor have I had formal design training. Yet, my career progression has largely hinged on my ability to communicate—whether it’s pitching ideas, aligning stakeholders, negotiating promotions, or simply collaborating effectively. Everything else falls into place when we master honest and candid communication.

Street smartness

Put a group of people together, and office politics will inevitably emerge. Some companies manage it well by hiring for cultural fit and swiftly moving out outliers. Others let unchecked egos create toxic work environments. Even if we don’t actively engage in politics, street smartness—powered by self-awareness—is necessary to navigate it. It’s not about playing dirty, but about recognising power structures so that we don’t become casualties of them. Staying naive to office politics doesn’t make us morally superior; it just makes us vulnerable. Once you have that awareness, use it to chalk your success path, without playing party to it.

Autonomy

Early in our careers, autonomy is a privilege, not a given. We have to earn trust before we can operate independently. But once we reach that point, the ability to own projects end-to-end is incredibly rewarding. It is truly a joy to see your ideas take shape, pitch new initiatives, and execute with minimal oversight—these are the moments that push us forward and boost our self-confidence. As a former manager, autonomy was one of the first qualities I looked for when identifying future leaders.

Influence

Every job description eventually boils down to impact. But impact is impossible if we don’t have influence. Whether it’s getting product managers to respect UX strategy, convincing developers to prioritise design details, or rallying a team around a vision—influence determines how much of what we do actually makes it into the real world. The ability to drive alignment and push for meaningful decisions is what separates designers who simply do the work from those who shape the direction of a product. My first promotion at Grab didn’t come from just doing my job—it came from pitching and driving a project that wasn’t even on the roadmap.

This in a no way an exhaustive list of skills you need to succeed in the corporate workplace. In my opinion these are the ones that are oft overlooked but can help you a lot more than just the right college education.

In tandem with the skills you do learn to keep climbing ladders, there are a few that make us complacent and too cozy in our comfort zones.

Skills you inevitably lose working in organisations

Curiosity and continuous learning

The pace of tech companies can be relentless. Early in our careers, we have the bandwidth to learn and experiment. However, as you progress in your career, and the scope of your role increases, it’s hard to keep up the balance between learning, doing your job and having a life. Unfortunately it is learning and curiosity that is the first to go out and often what leads to <insert time of life> crisis and eventual burnouts.

Case in point: I hadn’t picked up a new tool since Figma bulldozed Sketch. But since 2023, I’ve made it a point to learn something new every quarter—most recently Framer, and next up, AI agents. My latest experiment? Building an app with my partner.

Dissent

In theory, companies encourage strong opinions. In reality, those opinions need to align with leadership. The bigger the company, the less individual voices matter. You’ll quickly be silenced, however, if you hold a contrarian view. Companies are no place for your controversial opinions. I learnt this the hard way as a manager. The expectation is not just to deliver work but to mirror the beliefs of those above us. For a taste of that medicine, how many of us truly believe in return-to-office mandates, and yet, we enforce them anyway?

Creative instincts

Designing in large organisations is all about constraints—brand guidelines, design systems, stakeholder preferences, and scalability concerns. Over time, we stop pushing for bold, risky ideas because we know they’ll likely get watered down or rejected. The muscle that once drove creative problem-solving starts to weaken, replaced by a preference for “what works” over “what could be.” When you step away from corporate life, you have to retrain yourself to trust your instincts, experiment without approval, and embrace design as an art form again.

These are my personal opinions and you may not value these as much as I do. But maybe a good question to ask ourselves is how much of ourselves do we give up working for someone else?

Reflecting back on the skills that I’ve had to relearn now that I’m a free agent, has brought me a sense of peace that I had long forgotten about. And you could say it’s merely a consequence of being true to yourself, to which I’ll refer you to my previous question.

Skills you relearn as a self-employed designer

Now that we know the ins and outs of working as employees, allow me to get into the bright and dark side of working for yourself, freelance or self-employed.

Quality of craft

The first and most evident impact you’ll notice is in the quality of your craft. In organisations, you often rely on a peer group to give feedback on your work and improve it’s efficacy. Alas, when you work for yourself, you are your peer group. And like every coin, it has two sides to it. If you do not care about quality, it’s very easy to let it slide. Which is why independent freelancers struggle with the quality sometimes. But if you are a**l about it, you start holding a higher bar for craft, thus pushing you to better yourself. And since there is no supervision, you are your biggest critique. The downside, your design is never complete. Without the constraints of rushed timelines and rigid systems, you finally have the space to push your work to where you always knew it could be. Since I became self-employed, I can honestly say I’ve become a better designer than I was. Combine it with learning new skills and I’m almost super-person 👀🤦‍♀️.

Upskilling

As a free agent on the market, you are not guaranteed a pay check at the end of the month. You are required to go out and sell yourself, inevitably forcing you to take stock of your competition. And when a 20-something is knocking out drop-dead gorgeous apps out of their bedroom, you are forced to ask yourself “what is my brand value? What do I bring to the table?”. To stay competitive, I have to continuously upskill—whether it’s learning new tools, mastering adjacent disciplines, or refining my niche. I’ve learned more in the past year than I did in the last eight combined, simply because I had to.

It’s not that you cannot do this working in organisations, I know a few who manage to stay curious even when being employed. It’s a matter of priorities when you’re time poor.

Business acumen

Running a design business means we’re not just designers—we’re also founders, marketers, salespeople, and strategists. Understanding pricing, value propositions, and client relationships becomes as crucial as the work itself. Learning how to price our time rather than being defined by a salary is one of the hardest but most important shifts we make. A lot of self-employed designers I know still struggle with this, including myself. But you develop a keen sense of business, an understanding of how to drive profit and reduce loss, the essence of time and a thick skin when times get tough. All things crucial for a product designer, whether you work in-house or out, you need to understand the business to be able to deliver and drive impact.

Skills you need to unlearn for your peace of mind

Much like the skills you need to unlearn as an in-house employee, it’s not all roses and sunshine champagne when you’re self-employed.

Lack of control

Unfortunately when you work outside of the organisation or as a freelancer, you have limited powers of execution. You could have designed the most ground-breaking user experience but at the end of the day someone else takes a call on the priority and delivery of your design. This is often a reason why some designers choose to go back in-house, because the lack of control over your design can be frustrating to say the least.

Tying self-worth to productivity

When you work in-house, your calendar is full of meetings, deadlines, OKRs, and deliverables. Productivity is how we prove our value, and over time, we internalise it—we are only as good as the output we produce. But when you work for yourself, productivity is no longer just about output; it’s about thinking, experimenting, even resting. Some weeks will be incredibly busy, some won’t, and you have to unlearn the guilt that comes with not always being “on.” Because your value isn’t in how much you produce—it’s in what you create and the impact you make.

Trust your gut

In companies, we’re trained to seek alignment before moving forward—getting buy-in from stakeholders, making sure cross-functional teams are on board, ensuring everyone feels heard. You spend more time orchestrating consensus than actually executing. But when you work for yourself, there is no alignment committee. Clients won’t always “get it,” peers won’t always agree, and you won’t always have a sounding board. And that’s okay. The faster you unlearn the instinct to seek collective approval, the faster you can begin to trust your own judgment again and make decisions that serve the work, not the process.

Pay checks make you complacent, self-employment makes you risk-averse.
Choose your fighter!

In conclusion, I’m not advocating for one path over another—there’s a season for everything. This is my season to work independently, on my own terms. While I chase that, I wanted to reflect on the shifts between being employed and self-employment.

Where do you find yourself today? Have you made the switch either way? Let’s talk.

Until next time, ✌️!