written by
Justin Theng

The '50th Step' for Entrepreneurs

Growth Change Future 11 min read

Imagine your life as a total journey of approximately 50 steps. At the risk of sounding like I'm waxing philosophically, I've been pondering the many twists and turns of entrepreneurship and it's really a journey made with steps. Contrasted to how I used to think about business - as a house built brick by brick. Upfront admission here, throughout this post I use phrases and sayings we all know very well. They aren’t intended as puns, or cliches but do I think whoever coined the phrases stumbled upon wisdom I have only just started to discover. As such, these phrases which are now just thrown around casually, belie very profound things about business, and life, in my humble opinion.

If destiny were a total of 50 steps, which of these statements most closely resembles the way you currently think?

A) My next step, will determine all future steps.

B) My future steps, will determine my next step.

C) My 50th step, will determine my next step

What is Your 50th Step?

Fifty steps from now, where will you be? What will you step into? Will you be stepping up, stepping out, or stepping aside? In my experience, most people think and focus on the next step. In a way it makes sense because your next step will always determine the step after that, and after that, and after that... until all 50 steps are used up.

Let's say you want to walk to the most northern point you can get to by foot. You might make a plan, or you might wing it by heading in a general northerly direction. If it's at night, you may use a torchlight and only be able to see one step ahead of you at a time. Whether it is night or day, you may even go off course, and you'd need to step back toward the direction you generally want to head. But that is a waste of steps. But every step of the way, you'd be thinking about that moment when you take that final step onto the most northern point. Entrepreneurs are especially like this. We're wired for adventure and outcomes.

I challenge you, right now, to think about that 50th step.

In that picture, what do you look like? What are you wearing? Are you wearing a suit and tie or a more startup getup. Will you be fashion-forward or just well-fashioned? Will you be reflecting back on the last 49 steps, or just enjoying the 50th?

I have always imagined that as an entrepreneur, somewhere on my 23rd step, I’d have a team around me, of say, twenty five or so people who follow and trust me. The visionary. Maybe even think of me as their greatest inspiration. I would invest into them and train them into the very best they could be. I'd be a boss. A great boss. I'd want to of course be the best boss ever.

But then one day, I started to look beyond that and I didn’t like what I saw. With a view of 50 steps, my 50th step was stepping out of my business and handing it over to my kids. Because after all, what do you do with a team of people who depend on you, when you're ready to retire? Hand the business over to a stranger? No way! It would be my kids, I thought to myself, who would take over. My kids. Who might not even want to have anything to do with it.

Hmmm... Conundrum.

How could I be so selfish as to assume that they would want that? Had I considered their own individual gifts, temperaments and skills? Had I even asked them? No. I was willing to be an entrepreneur, defined by carving my own path. Inspiring others to do the same. But then I was going to be the biggest hypocrite ever, and lock my kids down from being entrepreneurial themselves, handing them a ready made business.


The more I looked at that picture, the more I realised, I’m no different to a dad who works 50 years in a corporation and expects his kids to also grow up and work in a corporation. Maybe even the same industry. Maybe even the very same company! That last one is the most shocking, and yet here I was doing the same thing - except I was building the corporation.

Okay so here's where I get a bit Freudian. Sorry in advance.

My 50th step, wasn’t a picture of me in the future. It was a picture of my own dad. The past, replayed, in the future.

Oh crap.

Changing the 50th

This started me on a journey of redefinition. I could choose to make my 50th anything I wanted. So I asked myself what I wanted my 50th to look like. I created a mental picture, and got it as clear as I could. Sights, sounds, smells, surroundings. I looked at the minutiae of the picture I created, and asked myself "why is that there?" For example:

  1. In that picture I am dressed in what I would consider trendy and fashion-forward. Why? It turns out, a core value of mine as an entrepreneur is that I don't want to ever build anything that would cause me to have to be something I'm not. To lose my personality. I want to stay fun, casual, and dynamic.
  2. In the picture, I had more than enough in the bank accounts. Why? To fund any project I could ever want to undertake, back anyone I want to back, give to any cause I wanted to, and go anywhere I wanted. But most importantly, I don't ever want anyone around me to feel like there isn’t hope. I want the capability to be generous.
  3. In the picture, my life is surrounded by cutting-edge technology. Why? Not just because I like the toys. Because I do. But it communicates another value inside me - Always do the undone, by accessing the inaccessible. It’s a pathfinding statement, an ethos for innovation. I didn't put it 'in there', and I can't take it out.
  4. In the picture, I am joy rich, family rich, time rich, and became financially rich, in that order. Why? I don’t want big complicated businesses. Just smart businesses. Businesses that nourish the endeavours of the points above.

From Here to Step 50

When I realised what my truly wanted my 50th step to look like I realised I had already been living in some measure of it. It brought a profound sense of freedom. Why was I willing to make my life more complicated, when all I really needed to do was fine tune, nurture and grow the life I already have? Told you it would get a bit deep. But screw it. This might help someone.

Is Everyone On Their Way To Their Ideal 50th Step?

I can’t say that my happy realisation would be everyone’s position at the time of reading this, but that’s why I'm writing it! Whether you feel like you are at step 1 or step 49:

It’s never too late to decide what step 50 will be.

Okay look, I don't have a crystal ball. Or a PHD in destiny creation. I'm definitely no Tony Robbins. So here's what helped me arrive at the epiphanies.

Acknowledging the Steps Already Taken

Looking backwards takes a lot more courage sometimes than looking forwards. There are no visible mistakes committed yet when you’re looking forward. But when you’re looking backwards, in light of the 50th, you are confronted with these things:

  1. Unchosen steps
  2. Wasted steps
  3. Steps back toward the right direction
  4. Steps to your ideal 50th

Unchosen Steps

When I looked back at my life, from around step 18, I can see that the first few 5-8 steps were not chosen by me. That’s because I was a kid, literally. I went wherever my parents told me to go. My family followed my dads steps all around the world, as he was relocated as his job demanded. Expatriate life. I literally followed in my father’s footsteps. These were unchosen steps. I hated some of them. But all of them were great lessons for later.

Being sent to boarding school in various countries at an early age caused some considerable relational damage to me, and my inner machinations, but at the same time I learned a fierce independence which still helps me today as an entrepreneur. I learned to see every region, city and culture of the globe as entirely accessible, where many others might see it as relatively inaccessible, especially so when looked at in a business sense (value 3 in my 50th step picture). Anyway, the point is that steps 5-8 were not chosen by me.

Wasted Steps

What’s interesting though, is that when I did begin choosing my steps myself, steps 9, 10, 11, were all diabolically different. A completely different direction until I really screwed up and needed to take steps back onto the ‘right’ course. Generally speaking, I actually began retracing steps 1-8. In fact I yearned for them. I missed them. I wanted to experience the expatriate 'global nomad' lifestyle again. I wanted my kids to experience it, because I really didn’t like the steps I chose for myself. They landed me in horrible circumstances. BRING BACK MY CHILDHOOD!

Steps Back Toward the Right Direction

At around step 20, after about 7 years of working in a successful advertising career I began to step out into my own business dealings. As you can see from my ideal 50th, that this was a step back into the right direction.

Business began going well and by that I mean I started to experience some of the goals I had for my life in general. More time, freedom to chose to spend it with my family, and giving to some level to the causes I wanted to contribute to.

But here is where I made a big mistake and went waaaay of course. I started viewing many of the things I enjoyed about business - the flow and hustle, the dynamism - as childish. I started telling myself I needed a ‘grown up’ business. Eat your heart out Freud. Somewhere inside there was a belief system (right or wrong) telling me to 'grow up'. To stop toying around, and be ‘mature’. Slowly, but surely, I began giving up on my deepest intrinsic values without even knowing I was doing it. I began choosing a 50th step that was rigid - traditional even - In which I looked more like a man in a suit, who would be the adoration of his staff, the steady and predictable money earner that was a great manager of everything in his life. Oh my goodness, I’d taken myself out of my 50th step and in place, inserted my dad. You guessed it. I needed to take steps back in the right direction.

When Step 25 Feels Like Step 1

Life is exciting, when you’re running. Pensive, reflective pieces like this invite you to walk, even to stroll through your thoughts and imaginations. Like a slow stroll through a big city, you notice things you never noticed before. Buildings of reason, statues of ideas, pavements lines with hedges of belief systems. “Has that thought always been there?” You might find yourself asking as you take in the sights and sounds of the inner-city of Brainopolis.

Have you ever wanted to design a city? When I was a kid (okay and also as an adult) I loved to play this computer game called "SimCity." I love planning the streets, placing the landmarks, stretching out the overpasses, lighting up the laneways. Have you ever wondered what it would be like if you were the President, Mayor or builder of a whole city? I wonder how much of our thinking, let's call it our inner-city, we designed. Conversely, how much was there when we arrived? Regardless, you, me, all of us - we live in our inner-city whether we like it or not.

Whether you geographically live in the country or live in an urban jungle, your brain is a sprawling metropolis of super-connectivity. Congratulations, you’re awesome even before you’ve had breakfast. I think the older we get the more the streets become superhighways, well used, and sometimes quite congested. Brain traffic jams! But we take the same routes all the same because it’s what we’ve always done. It becomes harder and harder to take the off ramps and try new streets because it just too darn inefficient! I find we take on a, 'been there, tried that' mentality. We just go on autopilot.

Treating step 25 like step 1 is like stopping in the middle of the highway and putting on your hazards. Have you ever been (actually) driving, and got lost in your thoughts, and lost track of where you're heading and how you got to where you are? That's what I'm doing. I'm stopping in my thinking freeways and asking, “Wait, where am I going again? How did I get here?” When you do this, the cars behind you are beeping, the cars going by are looking at you with bemusement, people are swearing and all you can think is, “Where is that off ramp?”

So this is where I'll end for now. But I'm curious about you, business owner. What is your ideal 50th step?

Business Leadership