A person standing in the street of a city with towering skyscrapers and neon signs, in a pixel art style. Image created in Midjourney.
When I talk to people about the path of entrepreneurship, many mention how appealing it sounds, but admit they lack the courage to pursue it. I always find this odd, considering those drawn to this path are usually self-starters, diligent workers, and, above all, dreamers–traits that far outweigh courage on this journey.
Perhaps, in the past, leaving a secure job required courage. But now we live in a post-COVID world with frequent layoffs. It is possibly more courageous thinking your 9-to-5 will be there for you in the long run.
So, what’s causing hesitation? Here’s my hunch, and reaffirmed by Rachel Gogel’s recent article in Print magazine. The definition of entrepreneurship, the idea of building something your own, has exploded. Now, being a founder comes with heavy expectations. Your business can't just be yourself or smaller; success is measured by scaling up to become the next billion-dollar venture or game-changer. But these expectations are just that—imposed by others. They're what you feel you should do, but what do you truly want to do?
The greatest challenge you'll encounter on the path of entrepreneurship is redefining what your business means to you. What are your own expectations, your personal aspirations for starting, owning and running this business?
💅 A personal anecdote
I started my consulting business on a whim and a need. After working in advertising, I realised I wanted more. I wanted to build experiences and learn from them—what worked, what didn't, and what the numbers showed. At first, I didn't have a specific title in mind, but I knew just creating websites wasn't enough. I wanted to solve problems and learn as I went along.
While I scoured the internet for everything on designing software and user research, I took the leap and opened my business. I ended up working with clients across various industries. Not every project was a perfect fit for my goals, but the practice and learning on the job was exactly what I craved. I did everything from designing for 0-1 startups to just filling in on tight timelines. I learned to manage clients, handle finances, and sort out taxes, all while taking my design skills beyond anything I learned in school or at agencies. Writing this makes it sound easy, but it required a lot. A lot of chaos, heartache, doubt and struggle. But it was exactly what I needed at that time in my life. I knew I was capable, but running a business, changing my career, and controlling my schedule showed me I was capable of so much more. As time passed, this realisation sparked a craving for new challenges, particularly to build and grow a product from within a company. So, I decided to put my business on hold and return to an in-house role.
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Further along in my product design career, I hit a roadblock. My AI project had paused further development, leaving me with more admin work than design work. The available roles in Seattle didn't excite me either—they all felt like the same. I craved a major change, a huge shakeup. Before I pursued a career in design, I loved the possibility of working in world history, sociology, and natural sciences. But I wasn’t one for sitting still in lectures—I preferred hands-on learning, and you can't really secure a job in the Smithsonian without a degree or two. I had given up on that dream, but with some savings and support behind me, I decided it was time to revisit it. I reopened my business and took on product design and branding projects to fund my Museum Studies courses.
I structured my weeks to balance client work and coursework. As I delved deeper, I had an idea. Considering the educational challenges in the US and the lack of support for teachers, I wondered if there was a product or service I could create to bridge this gap. I loved the educational games from my childhood and wanted to bring that same spark of curiosity to children in today's heavily connected era. I started pursuing a Masters in Teaching to better understand the process and directly experience working in a school, which was in desperate need of teachers.
I spent six months teaching in a first-grade classroom. As cliché as it sounds, the students taught me more about myself than I was teaching them. Interacting with children about their dreams made me realise I was neglecting my own—I wanted to travel the world and work with people from different cultures. And as much as I wanted to help children and teachers in the US educational system, I realised that another app, game, or startup wasn't going to solve the systemic issues on multiple levels. So, I decided to shift my focus. I wrapped up my exploration of museums and education, thankful for the insights gained. I traveled across APAC, drawn to the incredible wealth of culture and diversity in the region. Eventually, I found the perfect role, building projects across Southeast Asia.
I've run my business since 2012, but it's not traditional—it doesn't always stay open or have employees, and I don't plan to grow it. Like the women in Gogel's article, my business is precisely what I make of it: an oasis that provides independence whenever I wish to learn. As I grow, my business grows around my skills and expertise.
🧙🏻 Navigating this trial
Like redefining ambition, this trial requires you to examine and challenge the differences between your personal beliefs and societal norms. It doesn’t mean abandoning society—you still need its support to run your business. Instead, it's about selecting, choosing, and firmly sticking to what's ideal for you. Here are a couple of things to think through as you navigate this process:
What is the real motivation behind your desire to run this business? Is it for freedom, independence, or a passion for a specific field? What drives you beyond the potential for making money? Many people say, "So I can be my own boss and avoid dealing with people," but that's not realistic. Every business involves some level of social interaction, whether with clients, vendors, or customers, you will inevitably need to engage with others. Identifying your core motivation is crucial—it provides the foundation that sustains you during tough times, refocuses you when you're feeling lost, and offers a reminder of why you started during the good times.
What does your ideal day look like? And I’m not just talking about work, which is often our default focus when imagining our ideal day. Consider all the small details that shape your daily life. Are you a morning person or a night owl? What other aspects of your life need attention throughout the day—like family, pets, or hobbies? Reflect on these elements to determine how you can structure your business. For instance, I have a friend who, despite living in Asia, works exclusively with North American clients. They're a night owl and prefer working in the late hours. Even if it were lucrative, they wouldn't take on a client in their own time zone because the expectation there would be to work during the day.
What struggle are you willing to accept? No business is without its challenges. Leaving a corporate job doesn't magically solve all your problems. Like anything in life, there’s a bit of struggle that you’ll need to either find enjoyment in or be willing to endure on a daily basis. What is that for you? Personally, I don't mind spending all day in meetings and interacting with people, although others might find that exhausting. This shapes what I build my business around and what challenges I'm willing to accept. It's a common misconception that we must be grateful for and accept every opportunity in business. While it's true that in the early stages of a business you might need to take whatever comes your way to stay afloat, this approach left me feeling more burnt out than I ever was in my corporate job. So, it's essential to identify what you are willing to endure and what aligns with your capacity and goals.
I hope my topsy-turvy journey and these insights help you as you consider this path. The joy of entrepreneurship is creating something that aligns with you and your goals. You don’t need to conform; you just need to create your own definitions.