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False Realities of Being Self-Employed

I've always been a rebel at heart, but I like to use the term entrepreneur as an euphemism.

False Realities of Being Self-Employed


I've always been a rebel at heart, but I like to use the term entrepreneur as an euphemism.

Over the past five years, other than a one year stint at a boutique experiential marketing agency, I've run my own promotional marketing company, Brandcookie. I’ve also taken on the co-founder role of a collaborative travel planning app (to be announced soon). Last week, I accepted a full time job offer at Riot Games (creator of the massively popular League of Legends) as an event producer, which is a huge change because I haven’t worked at a large company since 2006.

I've been reflecting on the lessons I've learned while running my own company the past few years. On the eve of my first day of corporate orientation — on the eve of the end of an era and the beginning of another — I’m sharing these thoughts so others can learn from my mistakes. Behold, the top 3 false realities I encountered while running my own business, and my lessons dearly learned.

False Reality #1: You’re your own boss. 

If I had a nickel for every time I've thought this in my naivety, I’d… well, not have to be my own boss anymore. The truth is, you’re always answering to someone, whether it’s clients, customers, investors, employees, or co-founders. I can, theoretically, do whatever I want — except when it comes to giving my clients what they want. Add a demanding and high-paying client to the list, and you've found yourself a bonafide “boss.”

Make it a reality:

Stick to some standards on how much you should go out of your way to please whom you answer to. Desperation is your worst enemy in self-employment because you make choices you otherwise normally wouldn’t. Is the stress of dealing with a nightmare client worth not having to eat ramen noodles for two weeks? You might think so at the beginning (I did too), but one day, I hope the answer is no. Understand that your time and work is valuable, and you are the only one who can keep your best interests (and sanity) at heart. Like any good boss, draw a line for what’s appropriate and learn to say no — all the more important to do for yourself.


False Reality #2: You have a flexible schedule.

Sure, I love being flexible enough to be on a conference call while getting a pedicure or handling a client call when I’m grocery shopping in the middle of the day. But that’s the problem —  the client expects me to be reachable at any given moment, even when I’m getting my nails done or when I’m running errands. It’s hard to draw the line between personal life and work, because clients are calling me directly, I’m the owner of the company, and I’m directly and fully responsible.

The difference between working for yourself and working for a large company is that on my own, my “flexible” schedule is built in snippets around my work commitments. In working with a larger company, my “inflexible” schedule is routine and I have a clearer sense of personal and work separation. More flexibility doesn't always equate to more freedom; in fact,it means the opposite. When you run your own company, you’re more flexible — to be at the mercy of your work.

Make it a reality:

Learn to disconnect from work so you can keep a separate personal life. Show through your actions that you have work boundaries and people will be less likely to cross the line. Do not take work calls or emails after work hours unless direly urgent. If you do answer as a courtesy, let them know that you will deal with it in the morning or on Monday when you’re “in the office.” Make it clear that you have boundaries and you’re not at their beck and call, but are still reachable and can provide excellent customer service.


False Reality #3: You get to be passionate about your work.

I love planning events. It’s in my blood. I love the millions of moving parts —  except on the days when I hate the millions of moving parts. I’m passionate about building the events, but not the selling, negotiating or invoicing process, and most certainly not when I have to send friendly reminder emails for overdue payments. For every event I produce, there is an exponential stack of paperwork, administration, and billing waiting for my approval. Passion applies to the overall concept of what you’re working towards, but not necessarily to the daily routine of tasks that keeps it moving forward. There will be days that are not full of sunshine, and it will make you doubt your passion.

Make it a reality:

In TV shows, there are filler episodes necessary for developing a situation or a character more in order to advance the overarching plot. Understand that your daily work cannot always directly fulfill your highest passion, because there will be necessary tasks that need to be accomplished before you can move forward. Household chores in any small business all need to be done in order for your passion to be maintained and manicured. The earlier you accept this fact, the more fulfilled you will feel in being passionate about your work.

I love running my own show (despite the false realities I listed above), which is why I will be continuing Brandcookie’s client relationships and working on my collaborative travel planning app. However, I also love the opportunity to jump into the deep end of a larger company and lead the events team in producing some of the video game industry’s most exciting events. (P.S. I am a huge PC gamer.)

I’m more than aware of the possible and stereotypical “pitfalls” I may encounter with a large company on the cusp of being “corporate.” However, I want to discover any false realities for myself and learn to overcome them. Another opportunity of a lifetime is waiting for me.


Recommend this post if you like it, and feel free to drop me a line @eunicechen.