I run a bootstrapped Startup and I am struggling. To make ends meet, I work as a part-time marketing consultant.

My part-time job requires me to set up a marketing team for my client. This includes training a young team that’s fresh out of marketing school.

When you don the role of a teacher, you are bound to come across plenty of instances when you start having self-doubts. Their probing questions sometimes forces me on the backfoot and I go scrambling for answers. 

So far, I have managed to keep this arrangement going without coming across as a total idiot and that’s ‘mission accomplished’ for me.

So, how did I get here?

My journey as a novice entrepreneur

In the summer of 2015, my mid-life crisis had boiled over beyond the tipping point. I boarded my flight from San Francisco. Just before the flight, I gulped down on my favorite beer at the airport one last time.

It was a one-way ticket to India and It was a bitter-sweet moment for me.

I may never ever set foot in the US again where I had lived for over a decade but I was also looking forward to blazing a new trail as an entrepreneur at home.

Running an online business requires you to quickly come up to speed on a garden variety of software applications and understand a wide range of technical and non-technical stuff.

I was a complete novice and didn’t know where to start. But I was hungry to learn. After all, when your life is on the line, you end up doing things that you would otherwise not care about.

With all the enthusiasm of a starving person who magically finds himself at a Las Vegas buffet, I rolled up my sleeves and gorged myself on every technique and trick that marketing experts have shared through blogs and webinars. Whatever I learned, I put them into practice in growing my business.

Fast forward three years and I am the proud owner of an online business that’s still struggling and has some way to go before becoming profitable. 

Did I know what I was getting into?

Boarding that flight in San Francisco one last time is etched in my memory. That was a defining moment in my life.

I really was stepping into the unknown. Granted, I had saved some money for a rainy day, but I have a young family to support and couldn’t afford failure.

Everything that happened after I signed up for a new start far away from my comfort zone was unexpected.

In the very first year, I found myself cut off from the world when a major storm drowned my city for a couple of weeks and I was without Internet for almost a month (remember, I was running an online business).

I constantly struggled with hiring people and I am struggling with these issues even now.

I ended up selling my home to take care of some unexpected expenses that I never planned for. I couldn’t afford to rent a home so I moved in with my parents.

Last but not the least, I understood the value of money the hard way. Borrowing money from parents became the norm and after a while, it became embarrassing.

Not a single day goes by without me contemplating about the choices I made.

Looking at the bright side

My decision to roll the dice with my startup is by no means an easy decision. But looking back, there were some perks as well.

When you work for someone else, you can always complain about how the business is run and why it’s a complete mess. When you are the boss, you probably have yourself to blame for everything! 

I quickly learned to appreciate the fact that businesses aren’t always perfect. You can call it the enlightenment or the gift of seeing our careers from a new perspective!

I ended up doing some crazy stuff to get the business going and picked up new skills along the way. 

  • Became the star of my own Youtube videos,
  • Handled customer support on a 24X7 basis fielding all types of support calls (some of them really got to me),
  • Waged a lonely battle in resolving mysterious technical issues with my site, 

and the list is endless.

I learned the value of trust and commitment very quickly. 

When you find vendors and team members who actually mean what they say, it’s truly humbling to see how that trust can give you hope and confidence. 

I took the same approach when I dealt with my customers. Every time I fulfilled a promise, I felt proud.

Miracles happen when you have nothing more to lose! 

Even trivial decisions can change your life

In my case, the decision I made was monumental. Nothing I did was trivial. I threw a grenade in my otherwise perfect life just because I was bored with what I had and craved for some excitement.

If you are faint-hearted and value your sanity, you can still experience the joys of stepping into the unknown by making seemingly small changes to your life.

Let’s get back to the marketing team I am training for my client.

The other day, I was reviewing a blog post written by one of the marketing team members.

I requested this smart young man to add a hyperlink to a text on WordPress (an online publishing software).

In case you wonder how simple this is, here is how it’s done on WordPress.

Select the text and click on the chain icon. Add the URL and boom, you are done.

He promptly added a hyperlink without requiring any prompt.

I then requested him to make sure the link opens in a new tab when clicked.

His response was, “How do we do that?”

I pointed him to the gear icon that was staring straight at us.

He clicked on it and discovered something new that he never knew existed and I could see the delight in his eyes! 

A small lesson presented itself the moment the gear icon was clicked.

Just goes to prove my point about how a trivial decision or action can change your life forever – hopefully for the better. You just need to click on all those ‘gear icons’ staring at you.

The real question is, do we have the cajones?

It’s easy to be drawn into a comfortable life. Take the same path day in and day out.

For those that find happiness in the predictability, more power to you.

For those that are unhappy in their predictable life, you need to look for those small gear icons all around you and go for them. After all, trivial decisions give us the opportunity to make mistakes without serious implications.

The next time you do something, ask yourself if you can do it differently? 

Whether it is peeling a carrot or stopping at a store that you always drove by but never bought anything from.

You will probably discover a revolutionary way of peeling carrots or get a fantastic deal on your monthly toothpaste supply. What’s the worse that can happen anyways? Scrape your finger or pay an extra buck for toothpaste?

But that’s a risk worth taking.