Five Questions I Wish I’d Asked Before Quitting My Job For A Startup

My steady corporate job was great on paper — it paid well and let me travel the world, but it was also incredibly taxing and limiting. I didn’t want to be a cog in that system. I wanted to run my own business, but I never anticipated the challenges that came with it.

This post originally appeared on Medium

An SMS hitting my BlackBerry on Sunday evenings used to decide my destination and client for the coming week. I was working for one of the top three global strategy consulting firms.

“Tomorrow morning 5am, flight number AZ610 from Rome to New York.”

A life packed in a suitcase. A consulting life where you miss out on everything and everyone in life, except Excel spreadsheets. A fancy business life we are taught to be ideal slaves of, at top business schools whose degrees we are proud to hold.

After few hours of sleep, the private driver was taking me to the Rome Fiumicino airport so I could take my fancy business-class flight to NYC. Upon arrival, I was checking in to a fancy five-star hotel and heading to my client’s office afterwards. The salary? It was fancy, too. The company was proud to be among the top payers of the industry. Sounds pretty good, right?

But there was something wrong with this consulting life, though. I couldn’t stand this bullshit any longer and one day I called my parents:

“Dad, mum, I just quit my job. I want to start my own startup.”

My mum almost had a heart attack. It wasn’t the first thing a perfectionist mother wanted to hear after encouraging me to pursue my education at a top business schools with top grades, and having seemingly succeeded.

I tried to ease her distress. No chance.

“Mum, I hate it. All these consultants are pretending to be happy like they are taking happiness pills. I get to sleep only three to four hours a day. All those benefits the company promised don’t exist. Remember the fancy five-star hotel? I am working almost 20 hours a day and I don’t even enjoy it. Fancy breakfast? We never have time to have that. Fancy lunch, dinner? It’s just a sandwich in front of our Excel spreadsheets.

Oh, by the way, instead of enjoying a champagne, I stare at spreadsheets during my entire business class flights, too. The fancy salary? I never have time to spend a single penny of it.

I hate my life, Mum, it’s such a loser life. I don’t even see my girlfriend. I can’t fake it anymore. I want to start my own business.”

My parents had retired after years of a nine to five working routine at their secure government jobs. I knew that coming from a family with no entrepreneurial background, it would be difficult to explain my situation to them — leaving what seemed like a great job to pursue a passion — but I didn’t expect the call the next morning.

It was my mum on the phone:

“Sooooooooo, how is your business doing?! Is it growing?!”

No matter what I said, I couldn’t explain to her that a business needs more than one day to grow.

Partners, Friends And Your Social Circle

Having had the most supportive girlfriend ever, it was now time I shared the news with my friends who were busy climbing the fancy career steps in the corporate world.

I told everyone that I just quit my job to follow my startup dream. Some of my friends gradually stopped seeing me, probably because they thought there was something wrong with me since it was the second “fancy” job I had quit in a short period of time. I realise I was privileged and perhaps lucky to have the security of those jobs, but I just couldn’t find satisfaction and happiness in that work.

While the rest of my friends were supportive, there was, however, still something wrong with my relationship with them: I soon realised I was starting to pull myself away from social gatherings.

Every time I met with those friends, I didn’t have many updates to give them in response to their repeated questions like “So, how is your startup going? You are going to be the next Zuckerberg, right?” or “Oh man, we are so proud of you and we are so sure you will soon receive a huge round of investment.”

Trying to create and run a startup was a long journey and I was putting myself under so much pressure by caring so much about what other people thought of me.

Day by day, I was getting lonelier and more depressed as I avoided social occasions. My startup progress was not as fast as my social circle imagined it to be and I was fed up with telling people it took years for startups like Facebook and Twitter to arrive at where they are now.

The only comfortable place was next to my few entrepreneur friends, as though only an entrepreneur could understand an entrepreneur.

Cash, Cash, Cash

As if the social pressure and loneliness were not enough, I was meeting the mother of all stresses: running out of cash much faster than I had imagined.

This was killing my productivity and ability to make proper decisions. I was panicking and rushing to be successful and to make money.

One day, I even found myself asking my girlfriend for a few cents because I had no money to buy bottled water. I hadn’t anticipated that striking out on my own would be a difficult life full of ups and downs.

Today

Enough with the drama: more than two years have passed since those days. I am now writing this blog post in a beautiful resort in Phuket, Thailand, while enjoying my mojito. This is certainly nice, but no, I haven’t become a millionaire startup founder.

However, my business finally has a steady stream of revenue that allows me to travel the world and to work from wherever there is Wi-Fi.

There are, however, five things I wish I had asked myself before starting this painful journey. Five questions I believe every future entrepreneur should ask himself before taking the first step to entrepreneurship:

1. Are You Ready For The Social Pressure?

Your friends and family who are not entrepreneurs won’t truly understand what you are trying to achieve, and the pressure from them will be even higher.

I cared so much about what other people thought of me — so much that it took an intense emotional toll.

I was so hard on myself and punished myself with even more work so I could announce my success as soon as possible. That is, until the day I realised no one was really paying attention — so why should I focus on impressing everyone?

You are often no more than a few seconds of attention other people give to a Facebook status. In such a crowded and noisy world, most people just aren’t paying attention to what you’re doing.

If you care so much about what others think, you will waste your time trying to prove that you are successful instead of focusing on your startup.

Get a life. I got mine quite late.

2. Are You Single Or Do You Have An Extremely Supportive Partner?

As we get older, we share more of our life with our partners than with our friends or family. While I was lucky to have such an amazing girl, it was so sad to see many of my entrepreneur friends breaking up with their girlfriends and boyfriends along the way.

Doing your own business is tough — way tougher than I could have ever imagined. Your mind is constantly messed up with a million things going on and no other person, including your partner, really understands what is going on in there.

If you are not single, make sure your partner understands that your mind will often be a thousand miles away — it’s sometimes normal not to have a mindset even for a simple kiss. You should explain to your partner that this distance isn’t because of them; you’re wrapped up, perhaps too much, in your own thoughts.

3. Do You Have Enough Cash To Last At Least A Year?

Good, then multiply that amount at least by three because you will be running out of your savings way faster than you ever imagined. Along the way, there will be so many hidden costs, accountant fees, lawyer needs, broken iPhones or equipment — the costs always keep mounting.

Get ready for a smaller apartment, smaller food portions, and counting your cents, even if you never had to before.

The last few months before you totally run out of your cash will be especially difficult and the pressure will grow exponentially — I really couldn’t even sleep properly during that time.

Success will come slowly, and cash will burn fast. Be smart — plan from day one.

4. Are You Ready To Sleep Only Few Hours A Day?

Having escaped from the corporate consulting world, I was thinking I was finally going to live the dream by working whenever I wanted to work — until I read the following quote from Lori Greiner:

“Entrepreneurs are willing to work 80 hours a week to avoid working 40 hours a week.”

It all started by little wake-ups in the middle of the night. At the beginning, it was because I was too excited about my ideas and I had so many of them. I simply couldn’t wait for the morning to arrive so that I could start working again.

Then it escalated. I was working too much because I felt so encouraged by working on my own ideas that I wanted to do more. However, the more I worked and the later I went to bed, the more difficult it was to fall asleep, and the lower the quality of my sleep became.

As a result, at least two or three days of every week I had almost no productivity.

Don’t be fooled by over-hyped funding news about startup founders becoming millionaires. The stories behind the scenes have so many painful days, sleepless nights, and continuous rejections and failures.

The journey to success is long. Very long. Very often, too long, and the work takes a toll.

5. How Do You Define Success?

Each of us has a different priority list in life. For many people, money is the number one priority on the list, while work-life balance ranks higher for others. Consequently, people define success differently.

Depending on your definition of success, the difficulty of your entrepreneurial journey will differ, too. If money and public success are what matters to you the most, you are likely to have a hard time along your journey.

Remember these wise words:

“It is good to have an end to journey toward; but it is the journey that matters, in the end.”

Successful entrepreneurs are not necessarily those who raise millions of investment rounds. Don’t forget, they are one in a million.

There are, however, thousands of dreamers out there who manage to bootstrap their startups or live so well off on their own, but even they do not make it to the top of tech news.

No matter how much your journey fucks up your life or how difficult it will be, enjoy the ride and keep following your passion. As Tony Gaskin puts it perfectly:

“If you don’t build your dream, someone will hire you to help build theirs.”

How quitting my corporate job for my startup dream f*cked my life up [Medium]

Ali Mese, growth hacker, startup marketer, foodie, and globetrotter, is the founder of Piqers. Follow him on Facebook and Twitter

Illustration by Tina Mailhot-Roberge