Life after Startup – Trusting the dots will connect backwards

It was a sunny day in 2005 in the life of Stanford graduates when Steve Jobs walked on stage to give one of the most memorable graduation speeches of all time. Thanks to the beauty of youtube this moment was captured on camera and catapulted to millions of hungry aspiring entrepreneurs worldwide.

One of those hungry kids was me. It was 2010 when I first saw the video and especially one quote stuck to me at the time, and now, almost 12 years later it makes even so much more sense:

“You can’t connect the dots looking forward,” Jobs said. “You can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever”

This quote obviously sounds epic coming from someone that introduced beautiful fonts into all our lives after casually taking some calligraphy courses in his free time.

Now that I have the time to look backward, I thought it was also interesting to see how those dots connected for me and how that still affects me today.

Creating the dots

In the beginning of my entrepreneurial career I was 19. I didn’t exactly have much working experience, I definitely was not a great business student and I was a bit lazy. I would love to do many things and would naturally gravitate towards activities that were not really “sellable”.

Acting, student Radio, playing in a rock band and writing articles for the university magazine to make a bit of extra pocket money.

I was surrounded by business students that immediately would get more sophisticated entry level positions in Consulting at a higher salary and with clear career paths ahead of them.

Even in the first years of starting the business with my cofounder I was mostly the guy that sold his much more practical skill (Making websites).

I often felt useless and would wonder what I could study or do to be more valuable to the company. I tried reading a book about Javascript to help out with coding, but never really made it past the first 3 pages.

All my efforts at the time were directed at making the business successful, however they felt uncoordinated and not in a clear category that was valuable (like sales or marketing for instance).

However those seemingly unnecessary skills would later prove invaluable.

My years of experience on stage in front of large crowds came in handy when organizing trainings.

My experience at the radio was very useful when I started recording voiceovers for animations and editing videos.

Finally my university magazine articles came in super handy when interviewing clients on what made their story interesting and worth listening to.

And lately all these experiences again came together in my latest podcasting adventure.

I had never started any of those activities thinking that one day I would be doing what I ended up doing, but in hindsight I was always happy I did.

Dots can fade

Once we started getting a product market fit with animations we needed to focus our energies more.

Once a business is up and running, everything becomes more about strategising and improving. On a personal level It’s almost like I had lost the ability to just try stuff.

Every activity needed to become more carefully orchestrated into a cohesive ensemble of products and services and in service of the company.

The issue is that this also means we got more and more restricted by our current product offering and our existing convictions.

We were connecting the dots forward, strategizing and hoping our version of the future would come true. Almost always however that version never happened the way we expected.

While for a business this is the way to run and organize your resources, for me as a person it didn’t give me many new dots to connect for my personal skills. And while this didn’t impact the business very much, it did start limiting my creativity.

This is something very intuitive that I did in my student years, when I had nothing to lose and a wonderful randomness of following my interests. It got to a point where I would fail courses because I would prioritize making a new song, or memorizing lines or writing something interesting for an article.

Once I started working, those random interests that I took very seriously, faded.

Trust is key

One of the hardest parts of this period where I took more distance from the company is that I feel that I will just have to trust that whatever I do will eventually connect into something logical.

I have gotten so used to the rhythm and predictability of building a business proposition that I have to learn to let new skills happen.

I still catch myself trying endless cool slogans and mission statements for my new business ideas in my head. In a way I crave the focus and control that slogans can bring, but at the same time I know that businesses are not built on slogans.

Going off the worn path

If I look back at the spark that triggered me to make the animation videos, it was as basic as me thinking “hey I can do that voice” when seeing a casually narrated American animated explanation video (lots of words like “dude and stuff”) for the first time.

This then prompted me to think: how hard can it be to make a video like that? I already had most of the skills needed, all I needed was a good animator.

So really all I need is to trust that when the next thing I want to build presents itself, I will automatically connect the dots.

Or as Steve Jobs would put it:

“believing the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path and that will make all the difference. “

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