From Assistant to Boss: The Pros and Cons of Quitting Your Job to Run a Business

I’ve talked a lot about traveling – tropical islands with ugly lizards, Zip-Lock Band-Aids, and rooftop bars in Bangkok city – but I’ve barely touched on what it’s like to run my own business. For years, the idea of running my own business was nothing more than another one of my crazy dreams – you know, the type everyone adores, but no one really believes, yourself included. Maybe some day, I told my 20-year-old self, when my hairs turned gray, I’d open that snazzy restaurant in BudapestSomeday, 30 years from now, when my savings account was fat from decades of being someone else’s corporate slave, I’d follow my dream.

Well, that dream happened 28 years before I expected. Maybe it was the angst I had towards my job or the travel bug I caught a long time ago, but I couldn’t wait a moment longer to upgrade my title from the assistant to the boss. So I broke my lease five months early, gave notice to my employer and bought a one-way ticket to Thailand. I had nothing more than a start-up, a small savings account and a backpack of possessions to my name.

Saying goodbye to a steady income to invest my time and money into a start-up I co-founded, all while living cheaply around the world, is the probably most difficult thing I have ever done. My excitement was coupled with self-doubt, fear, frustration, and a depleting bank account. What if it failed? What if I had to turn around after a month on the road? Was I naive to think this dream could become a reality?

Maybe I am naive, but it’s been nearly three months since I received my last paycheck. I’m living cheaply in Southeast Asia now and running an import/export company that’s less than two years old. Yes, I’m living my dream. That’s not to say the entrepreneur lifestyle is all peaches and roses. Our business is very much coupled with highs and lows; triple profits one day, followed by no profits the next; 60 hours worth of work one week, then less than a dozen the next; thousands of dollars worth of inventory one month, then low or no inventory the next. It’s a high-low lifestyle with bad, good and great days mixed in a row. There are pros and cons to running your own business – these are just a few of my entrepreneur highs and lows:

1. Stepping up to the Position of the CFO 

Pros: Revenue is exciting, profit is thrilling. Watching the bank account grow is, hands-down, one of the best aspects of running a small business. We started our business with little more than $100, now it generates $1000s in revenue every month. We’ve seen our profits double, triple and quadruple over the past year. We hope to turn our business into a million dollar asset one day — and we’re confident we can because we believe anything is possible in business.

Cons: My co-founder and I have the final say on all financial decisions, which, while empowering, it’s also stressful. I’m always a little uneasy when we spend $2,000 or $3,000. If the investment is bad, the blame is on us, not the guy with the posh office overlooking the city. My salary is also completely dependent on our business’ success. Rather than paying ourselves, we reinvest 50% of our profits. It’s a little intimidating watching my savings account deplete more and more every month – but also exciting knowing the day I receive my first paycheck is not far in the near future.


Moving the “Office” from Thailand to the Philippines.

2. Actually Working When You Could Be Lazing on the Beach Drinking $2 Beer

Pros: I love setting my own schedule. I’ve gotten into the habit of starting work around 10:00 or 11:00 a.m. every day. When I’m moderately busy, I work from morning to mid-afternoon, seven days a week. Of course, my schedule is flexible. I can sleep in, take a long lunch or enjoy a day off whenever I like. It’s beautiful being able to control your own time. I’ve found I work around my natural moods. For instance, I work when I’m alert and motivated and rest or play if I’m feeling tired or unproductive.

Cons: When I first made the switch from employee to business owner, I lost all my motivation to work. I was so thrilled to be free from the 40-hour workweek that I spent my time socializing, exploring, reading and blogging instead of working. It didn’t help that our business had tripled its profits in the months prior either. For a little while, I think my co-founder wondered if I would ever “show up for work”. I eventually found a routine that worked for me – but it was a habit not easily acquired.


Moving the “Office” from Thailand to the Philippines.

3. What Should My Business Card Say: The Web Designer, The Marketer, The CEO or The CFO? 

Pros: Being the boss is awesome. No one can tell you what to do or when to do it. Being top dog means you’ll always have the highest salary and the most pride for your company.

Cons: When you run a two-person company, you’re the man in charge, but you’re also the customer service representative, the web designer, the marketing department, the accounts receivable, and so much more. You’re constantly learning and developing new skills, which can be exciting, but also time consuming and challenging. For the first half of this year, I read only business books. My co-founder is a ferocious consumer of entrepreneur podcasts. Both have been tremendously helpful in aiding us with learning how to run a business on our own.


Taking a break from work to walk on the beach.

4. A Portable Office With Wi-Fi 

Pros: I love being able to work from anywhere in the world (provided internet access is readily available). One of the primary reasons we started our business was so we would have the flexibility to work and travel. Right now, I can’t imagine a better life than the one I have now: we travel every week or so, with plans set no farther than 5-7 days in advance. Maybe, I’ll tire of the nomadic lifestyle someday, but, even then, as my own boss, I’ll have the option to live wherever I please.

Cons: Working on a Thai island with a ton of vacationing Europeans can be a tiny bit distracting. Sometimes, it’s hard to find motivation to work when the location is begging you to explore, to relax or to party. Another con of not having an office space is the lack of readily available wi-fi. We have had to intentionally take a day off now and then because we didn’t have access to a fast, reliable internet connection. There are also places in the world we cannot venture right now because of our dependence on wi-fi.


The Portable Office in the Perhentian Islands, Malaysia.

Are you an entrepreneur? What are your favorite and least favorite aspects of running your own business? Do you want to start your own business, but can’t? What’s holding you back? Tell me in the comments section below.