Work For a Startup Or Create a Startup?

“To be, or not to be” is the famous opening phrase in the so-called “nunnery scene” of William Shakespeare’s play Hamlet. Now, 400 years later. We are asking ourselves a slightly modified, yet similar question. That is, “To work for a startup, or to create a startup;”. Or the more dramatic one: “To work for an entrepreneur or to be an entrepreneur. That is the question.”

The tides are turning.

When I was born. The phrase “starting a company” was not in the vocabulary of many people. At least in my country. Yes, regular people were opening small shops, restaurants, tiny libraries, game rooms where you pay per hour to play on a PC – similar to a coworking space but you don’t co-work, you co-play. Overall though, the majority of the population was tight to the steaming economic system – i.e., being a cog in a gigantic organization.

A factory worker. An accountant. Salesman. A teacher in the local school. A chef in a local restaurant. Or, a lawyer or a doctor, if you were lucky. The last two were considered a dream job when I was a teenager.

Yes, a dream job! Less than 15 years ago, becoming a doctor or a lawyer was the most prestigious thing you can do with your life. Of course, no one with his right mind was pursuing these careers with the sole purpose to help people – while the underlying purpose of these jobs is exactly to help people. The aim was to get rich. To get more money. To wait for the high school reunion so you can go with your new, just imported foreign car and tell everyone how amazingly rich you are while they are tossing coal in burning chambers somewhere deep underground.

I’m purposefully not including occupations like a singer, an actor, or a musician. How could I? Do you know that the success ratio of a wanna-be musician nowadays is 0.000002%. Yes, you read that right. It’s 0.000002%.1 I bet that number was closer to zero in the 90s. After all, people back then didn’t have SoundCloud, Spotify, or YouTube to promote their songs.

But let’s get back to our main question here: To work for a startup or to establish a company?

Why do I think that more and more people are asking themselves this question?

Well, unless you’ve been living under a rock or something. For the past 10 years, all thanks to one single invention – the Internet – the chances to monetize your passion – i.e., do what you always wanted to do – even if this is doodling pictures that are like created by a toddler, is now something that is actually possible.

Thanks to the power of the Internet. We can now, theoretically, all do what we want. Earn money our way. Be our own bosses. Don’t take orders from anyone and create a lasting mark in the world so people can mention our name even after we are gone.

We can create an Instagram account and share our drawings. Then, we can set up our own website, blog about our drawings, and sell our drawings. All of this, without leaving your apartment.

But is it really that easy? And more importantly, is this really what we want?

Do we have to ditch the cozy job and create our own Silicon Valley-style startup where we are saying that we are saving the world while in reality, we are gluing even more closely people to their phones?

To help you decide, let’s observe the possible options:

Not To Be: To Work for A Startup


Since you’re born, the world is preparing you to get a job. Our school system revolves around you getting a job at some point. Your teachers, your peers, your parents even. Everyone close to you is obsessed with helping you get a nice job that will help you earn a living.

What about your dream of becoming a graphic novel artist?

“That won’t pay the bills,” your father mutters while handling you a brochure for the regional school for lawyers. And with time, the future you envisioned while you were young fades. The repetition of the everyday life where you’re trying to present yourself as more likable, adjust to others so they can hire you plus, constantly think about money, murders your childhood dreams.

Of course, not everything about getting a job, i.e., working for someone else, or working for a startup is bad. Especially working for a startup.

Most of the software firms these days make your nonworking experience – when you are off your desk, even if this rarely happens – feel like you’re at a 5-star resort. Drinks. Food. Big spacious gaming rooms and relaxation areas. Ridiculously expensive toys that are unusable but look cool on the careers page of the company. People cooking meals. Work-related vacations with your coworkers on a distant island where drinking water is replaced by drinking alcohol…

Yet, regardless of the amount of food that is available in the kitchen, it’s still a “not to be” kind of experience.

During the short breaks where your mind is healing from the tedious working sessions and trying to prevent permanent mental health issues, you remind yourself about your dream of becoming an artist. A painter. Especially if the work you do is helping creative people – as most startups are.

Companies like WebFlow, Shopify, or Squarespace state that they want to empower people and help them create their own future. Live a life doing what you love. But what about the people working for these companies?

There are more than 7,000 people working for Shopify, for example.2 But from these 7,000 people, I bet that only one person is doing what he actually wants – the founder. The rest? They simply have a job.

The paradox is that you work for a company that helps people fulfill their dreams by building a business related to what they love doing but you, yourself, are not building yours. You are like the helpful sidekick. Like a backstage worker, ensuring that everything is properly running for the stars but never actually stepping foot on the stage you helped build. You just exist in the shadow of the people you’re supporting.

To Be: To Create Your Own Startup


There’s a weird shift in the conversations between parents and children.

When I was young. I remember how my parents told me that I can become whatever I want. “Mom, I want to be a pilot!” or, “I want to become an athlete!” her reply, always supported with a joyful smile, was, “Of course, dear. You can become whatever you want!”

With age things dramatically changed though. According to my parents, I could still be what I wanted to be, but only if it was something that was going to get me a decent job.

The talk about doing my own thing or exploring my talents was no longer on the table. It was all about doing things that would make me a likable employee who can fit in, blend in, call it whatever you want.

I know that my parents were doing their best to navigate me in the real life. And although it was kind of demoralizing, I get them. The currently available opportunities thanks to the Internet were not available when they were young. And they still don’t quite understand the power of the web. For them, the only route possible was for me to get a job. That was – as my mom used to tell me – the safer way that pays the bills. My desires and ambitions were no longer important. It was all about entering this corporate world where you are supposedly financially protected by following orders – and we all know that this is not even close to the truth.

This leads me to…

Do you want to be a cog in a gigantic machine or do you want to be the machine itself? Do you want to work for an entrepreneur or become an entrepreneur?

It really depends.

If you work for a startup, you usually have one main task – accounting, coding, writing, supporting clients, etc. Yes, probably you’re doing a lot more than what your job description states but that’s a whole other story. The point is, you are responsible (and care) for one tiny part of the product you are creating/supporting.

Conversely, if you are to take the “to be” route. It’s all on you. You should care about everything.

  • Invoicing clients? – Bring it here.
  • Designing a website? – I can make it happen.
  • An angry email from a client? – I can reply while having lunch.

Simply put, it’s hard work to be your own boss because you’re not only the boss, you’re also the support guy, the billing department, the social media expert… And it doesn’t get easier, it actually gets harder with time.

Surprisingly, people all over the world are ditching their cushy jobs and starting their own projects.

For example, I recently read the story of Bryan. A person in his 40’s with five kids who quit his dream job at Amazon to create his own software company. Or, the story about Cole Schafer. The person who quit his job at a local agency a couple of years ago to become an advertising guru by day and a poet-writer by night.3

And these two stories are not exceptions. They are becoming the norm.

There is this thing big news sites are labeling as The Great Resignation. Simply put, after spending more than a year working remotely because of the pandemic in 2020. More and more people revaluated their relationship with their jobs. People don’t want to travel an hour to the office. They want to spend more time with their families. They want to live life on their own terms. And, as reported by the 21-year-old Stephanie Becker… “Waking up at 3 a.m. to go do something I didn’t want to do, with people I didn’t want to deal with, didn’t make me feel good.”4

But something other than the unwillingness to drive an hour to the office makes people take the entrepreneurial path. People now see that it’s possible. They see how other people are “making it.” Doing their own thing. They read stories of solo founders who are living their dream life. They watch videos of people who are working in their pyjamas.

They see all these things and they say to themselves, “Since others are able to make it. I can too!”

Besides, as I already mentioned above, if you work for a startup that is helping people make a living online. At some point, you get to ask yourself: “Why am I just an observer of people pursuing their dreams? Why don’t I pursue my own dream?”

This existential realization usually happens once you have enough food on the table, a stable relationship, enough money, but you are still not happy. There is still something missing.

According to Maslow’s needs theory, once your basic needs are fulfilled, you need self-realization to reach the highest level of happiness. You want to express yourself. To reveal your true self to the world. Not hide it inside a cubicle.

And these days, showcasing your hidden desires can happen in so many ways.

Starting a company revolving around your interests and your skills is relatively easy these days – at least on paper. You figure out what you want to do. You probably Google stuff online to figure out what’s already out there to clarify your idea. Then, you simply start doing it online – whether this will be by blogging, creating podcasts, uploading videos on YouTube, or simply ranting on social media… It’s up to you to decide.

That’s the best thing about the tools available online. They help people express themselves. Share their stories and their talents. Most people still believe that the WiFi connection is God-given because it allows you to stream movies and play video games all day long but that’s just an appetizer. The main dish is the ability to show your true self. Or in relation to the title of this post, “To Be!”

But it’s not all that simple.

The most dangerous thing about starting your own startup is adopting the belief that things are going to be easy – they won’t be.

There are a lot of different nuances to starting your own thing online. Don’t be fooled by the clickbait tutorials on YouTube and the articles that state that it will take you 30 minutes to start your own site. Starting a site or opening an online shop is the easiest thing – even if you’re not a developer. The hard thing is marketing your site. Making people believe in what you do so they can trust you with their wallet.

Or in simple words, it takes time. Trail and error. Money. Iron nerves. Patience. Coping with uncertainty. Willingness to learn. And a dose of luck.

Even if you have all of those, a lot of times you’ll want to quit because your progress will be painfully slow. There will be other times where you’ll feel alone and unsupported. And, there will be also times where you’d feel emotionally and physically exhausted. Misunderstood. Angry because “it’s not working.” Feeling like a fraud. Feeling like a failure because you’ve spent years building something that seemingly no one wants.

What to do at these times of distress?

This leads us to the final section of this how-to post about whether to be an entrepreneur or to work for one.

Create A Startup While Working for a Startup


Around my 25th birthday, after reading a bunch of self-help books, blogs, and articles online, I decided I wanted to be the person making content instead of just the person reading the content produced by other people.

I didn’t quit my job. Nor did I shared this intention on my social media profile. It was simply something I started doing on the side. I wasn’t a good writer – not that I’m good now. But I’ve greatly improved after years of pushing keys while everyone else is sleeping. It took me years of failed attempts to understand what’s good writing all about and how a website online should be organized.

Being passionate about something doesn’t necessarily mean that you should quit your job and put yourself in an unfavorable financial situation.

Personally, I believe that if you want to follow your gut feeling. Your instinct. Do what you’re passionate about. You should do it gradually. Start building something on the side and move on to doing it full-time till the project is at least half-baked. When there are enough people listening and you know what works and what doesn’t.

Of course, there are different sides and different opinions. Some say that if you’re going to do something, you should go all in. Others say that not everyone is cut out to be an entrepreneur. Third, continuously share the success stories of people like Joe Rogan who recently signed a $100 million deal after a decade of podcasting.

Getting inspired by the success stories of others is a dangerous route. Especially people like Joe Rogan. He’s an outlier. He’s not the norm. Ever heard of another successful podcaster besides Joe Rogan?

Well, I haven’t.

This doesn’t mean that you can’t make it. It means that you have to be prepared. Prepared for the unexpected.

This is the main reason I believe that if you want to eventually stop working for a startup, you should first create stuff on the side.

Here are a couple of other reasons on why you should start your business as a side gig first:

  • Testing: This is probably my 8th site and my 10-year anniversary of producing content online on the side. My previous websites no longer exist. And while I literally spend years on projects that are long gone, I don’t regret it. I learned a lot of things about creating websites and producing content. Without the previous mistakes, I wouldn’t be here now.
  • Clarify your idea: Making content online is one thing. Figuring out how to make money from the content your produce is a whole other game. Usually, you’d have to produce content for free without getting any money for months – sometimes even years. This helps in several ways: You understand what type of content you want to produce – what you like doing. You build an audience. You figure out what you can additionally do to make money from your site.
  • Anticipate problems: Creating an online presence is surely not a walk in the park. Daily, you have to resolve different problems related to your site or customer-support type of inquiries. Usually, in a job environment, you’d ask a colleague for help. But since you’re the only person working for yourself, you’d have to figure out things on your own. This experience helps you see what type of future problems you can expect and allows you to create a better plan.
  • Stay afloat: The second major problem when creating your own thing based on your passion is having enough money to support yourself till you start earning enough money from your thing – the first is clarifying your idea. Some people recommend getting your first paying customer before quitting your primary job. Others, getting enough to cover base living expenses. Still, it really depends. Making a couple of sales is not that hard. You need to think about how you can make recurring revenue.
  • Emotional calmness: Actually, when I think about it, handling your emotions is probably the main problem when you want to transition to a founder. The benefit of having a job is not just that you get a regular paycheck. You also get a sense of security. In most of the situation, you know that you’d have the job the following month. When working solo, you don’t really know what will happen tomorrow. That’s why it’s so important to add your emotions to the equation. Having enough cash and enough paying customers is of real importance to keep working on your project. Otherwise, you’d have to deal with unsettling emotions that are only distracting you.

All in all, by side-hustling, you get to see what running your own company means. What needs to be done. How much do you really need to support yourself and your family. And most importantly, do you really want to do it.

There is a ton of content that will help you get started with your online project. But getting started is the easiest part. Few people get past the getting started phase. The ones who endure the initial problems are the ones who can actually morph their passion into a career.

Some Closing Thoughts

Even if you don’t want to be your own boss. You love the security your job provides. You probably still secretly envy the ones who are sharing their progress on YouTube. The ones who post pictures with their laptops near the beach.

Probably you are working your dream job for a local company. Probably you’re indeed the type of person who can’t manage a company on its own – a company of one. That’s absolutely fine. Still, I believe that everyone should at least taste the experience of creating something online. I’m not talking about setting a goal to earn millions. Simply create something related to a thing you care about and see what will happen.

Don’t focus on making money. Enjoy the process. Test different ideas. See what will happen and even allow yourself to quit if things don’t work out the way you’ve hoped. Considering it like learning how to play an instrument. The whole process of creating a small project online is a great learning experience. Besides, it will teach you things you can later transmit to your kids.

Who knows, probably these hours you’ve allocated on creating something online will change the way you talk to your kids about making money. You will probably stop pushing them to get a job and instead, inspire them to make their own jobs.

“The only thing worse than starting something and failing… is not starting something.” Seth Godin


  1. Ong, JJ. Why Being A Sustainable Musician Is So Much More Important Than Being A Successful Musician. The Songwriter Music College.
  2. Shopify: Number of Employees 2013-2021.
  3. I love his work. You can listen to his story in this podcast episode.
  4. Liu, Jennifer. I’d rather bet on myself’: Workers are quitting their jobs to put themselves first. Make It blog.
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