I was once a wild eyed, ambitious and fearless 20 year old. I wanted to work for Microsoft or Google. I wanted to earn my first million before I was 25. I also wanted to start my own company, and become one of the first Kenyans to get Silicon valley success. The funny part is, half my Computer Science class seemmed to have the same ambitions. The competition would be fierce.

It’s been nearly 20 years since, and if you did a mind map of where all of us landed, it would give you a headache. The lesson? Man plans, God laughs. Which begs the question, what is the role of dreams, ambitions and aspirations? If our destiny is a function of a myriad of factors, the bulk of which aren’t in our control, then what is the role we play? Do we have true agency over our future, or does luck, fate or divine will really get the final word? And if so, who’s to blame those who descend into nihilistic, free spirited existence devoid of 10 year plans?

Don’t get me wrong. I still have goals. I have dreams. I have aspirations. Not earning my first million before 25 didn’t stop me from working he hampster wheel of a professional and business life. How about we just have some fun with this topic today.

After about 20 or so years of dissapointments, failed endeavours, regrets, and if-I-had-known-better moments, I have two perspectives to share.

Being your biggest cheerleader, and worst Critic

A major source of my innumerable mishaps in life came from decisions made impetously, with little to go with by way of information and appreciation of the downside. I obsessed over the ‘What if it works?’ posssibilities, and relegated the ‘What if it doesn’t work?’ question to the recesses of my mind. In fact, when anyone would question my decision in a manner that suggested I may have been off track, I would derisively bucket them under my haters list.

One of my biggest failures in life was a crowdfunding business for which I risked both my reputation and my family’s financial wellbeing, by raising over Kshs 10 Million in debt within the first year. That’s how much I believed in it. I’ll never forget one particular, and I must say savvy, potential investor who grilled my CFO and I for two hours about our offering. He thought that the business model we were running was akin to a financial house of cards, which would inevitably come crumbling down. He of course refused to invest. We of course hated him. How could he not see the vision we had? And who did he think he was to question us like that?

In retrospect, he had valid points. Points which if we had heeded in a timely fashion, would have saved us millions in losses in the ensuing months.

This, and other painful restropective experiences taught me to both believe in, and at the same time deeply question my aspirations. Not an easy feat though, especially in the early, honeymoon phase of new ideas. Recently I spoiled a fledgling business relationship by asking, ‘What if it doesn’t work?’. Evidently the founder wasn’t ready to face that possibility, even hypothetically. So I bowed out, and wished him well.

Start small, and iteratively grow Big

The bible in Zechariah 4:10 cautions us not to despise the days of humble beginnings. I’ve been in many startup circles, especially in the Tech world where I work. Every startup founder believes theirs is the next Uber, or Google or Airbnb. They are the ones the world has been waiting for, and their growth projections show it. A company with no revenue wants to be viewed, and valued based on a presumed million dollar Annual revenue that will miraculously come within 36 months.

I joined the Marketplace when 23 year olds in Silicon Valley were becoming billionnaires through mind boggling venture capital raises. I drunk the coulade and could envision myself in that league. Many of us did, none got anywhere close. Years later, I founded a business community that sought to drive the narrative of progressive, revenue driven growth. I encountered relatively unknown, non-headline seeking visionaries who had built solid companies that made millions, paid taxes and employed tens, sometimes hundreds of employees. They had been at it for 5,10,15, 20 years in relative obscurity, winning some, losing some, learning along the way, and growing at a consistent, sustainable pace. They became my Heroes.

For them, staying humble allowed yesterday’s foolishness to fuel their current brilliance. Their approach to biting what they could chew gave them what some call staying power.

When you accept that your dream may be foolish, your chances of success increase. Funny huh?