The Messy Middle


From how our human brain is primed to memorise information thanks to storytelling format, leading to remembering the beginning and the end of a story… but what about the middle?… well it’s messy. I loved reading “The Messy Middle” a few years ago, a book by the founder of Behance, Scott Belsky, who shared his philosophy and journey leading to the acquisition by Adobe. What struck a chord with me was how he put the light on an unseen period of a business. Typically removed from the montage of the final movie or put in fast forward like Rocky Balboa’s actual training was a total 5 min of the whole movie 😆… because it’s not sexy, it’s messy…

In short:

  • Before Drilling The Tunnel
  • While in the tunnel
  • Seeing the end of the tunnel

Before Drilling The Tunnel

When I think about digging a tunnel, for example the one under the Channel between France and The UK, we might think of just starting from A to B. It’s what seems to make logical sense.

But for practical reasons (like saving a few decades) the boring starts at both ends of the tunnel. It’s more like: A -> B <- C. In business, everywhere in the literature everything is presented in funnels, flywheel and in “logical” sequences. So when I design/think of a new offering (product or service), I think in this basic order: 1. positioning 2. marketing (attract) 3. sales (convert) 4. delivery (delight/retain)

But, when starting with the execution of something new, I need to almost go against all the previous “thinking” steps and start in the opposite direction: 1. delivery (building at least a minimal capacity to deliver / MVP) 2. sell to low hanging fruits (problem aware people) to get market validation 3. Use testimonials from first sales (results) 4. Refine positioning to become sharper

Just like what I learned about the tunnel construction, you want to course correct well from the beginning or the deviation might be impossible to re-align. Once the tunnel is connected, then we can accelerate everything. I get it, it’s not a perfect model, so remember.. “

All models are wrong, but some are useful”
- George E.P. Box.

The point is that when jumping into something new: a new service, a new product, a new business… it’s so far from a straight line, but rather a dynamic dance on two feet, one step on a foot, then use the other until finding the balance and the rhythm.

My takeaways for entrepreneurial engineers

  • Be sure to recognise when doing something new, and accept it will not be a straight line.
  • Don’t start with planning: I learned this from events, Retro-planning <-, then planning -> (start with the end in mind)
  • Embrace the upcoming, yet invisible, messy, unbalanced and chaotic period.

Reaching that balance is the point of the messy middle.

While in the Tunnel

I’ve been to quite a few personal tunnels. Some that worked out against all odds, some that were mere dead ends. In the moment it feels long, very long ...

All of our values get tested, especially when it gets dark in the tunnel, to fight all the headwinds of self-doubt, people (imaginary or real) telling me “why are you digging a tunnel? you could just take the ferry”, not seeing anymore the progress because you can’t see the beginning of the tunnel where you started on one end, and a wall on the other that you must keep drilling. That’s when my faith, my values are tested. Unshakable faith can make the difference, where I believe in the unseen (yet) while all my senses send me a different signal. My resolve is constantly tested especially when navigating in unknown territory for me, while I am learning from those who walked a similar path before.

“If you don’t know where you are going, you’ll end up someplace else.”
- Yogi Berra

Having a strong picture of the (right) end goal is so critical in those moments, otherwise we can end up somewhere we don’t want, or quit. There are times where it makes sense to quit as highlighted in Anne Duke’s book “When” a great book for those running a “zombie business” (neither dead nor alive) to ask oneself the right questions and sometimes it’s ok to stop. It’s just one way things can end; in the journey I am on it’s just the beginning.

My takeaways for entrepreneurial engineers

  • Without focus and direction, any light wind can derail you.
  • Whatever values we claim we have, they will be tested together with our character.
  • Don’t believe only what you see 👀 cultivate your resolve (or your faith) with a touch of positivity.

The Light At The End of The Tunnel

Someone mentioned how dopamine, the reward hormone for making progress, kicks in when we see afar a sign that we are close to a goal or milestone. It gives a strong pulse to make it across the finish line. I know this will come, I remember it’s not likely to be something we can control. What we can control is to put in the work, consistently without giving up, we eventually get to see that light at the end of the tunnel. It came to me in the past in many forms:

  • In 2015, “we want the expansive one” a client exclaimed unanimously for a project we suggested that was double their budget. This was the first signal, light, that we were right to push for a second option that regardless of its budget would actually fulfill the client’s status desire.
  • In 2022, signing our first subscription client after years trying to design such a service without success. We were tested, by boldly (and politely) refusing to pitch for a tender, however we suggested a better way more strategic and aligned on customer’s context.
  • Last week, I received a WhatsApp message from my technical founder coaching student from last year. It made my week, will know more details when we meet about the specifics.

The joy of seeing that light at the end of the tunnel washes away all the pain of the messy middle instantaneously. I believe that’s why we don’t remember how hard it was to get certain wins, but when we think about it, we are grateful we’ve been through that pain. It helps us push our limits (for next time), extend our boundary of knowledge and that’s what helps us constantly advancing.

My takeaways for Entrepreneurial Engineers

  • Don’t avoid the pain.
  • Lean into it even with fear in the belly, that’s the definition of courage.
  • The pain will be replaced by incredible fulfilment once on the other side.
  • You might see a wall in front of you, just climb it, once on the top you’ll realise how the world is bigger than you thought and where are the next walls you need to climb.

After the rain the sun, after the pain the reward. It will seem obvious and easy in hindsight.

That's it for this week, I hope this was helpful 🫡

PS: A few scenes from my favorite prison break movie, the old but gold "The Shawshank Redemption"

The Entrepreneurial Engineer

From aerospace engineer to entrepreneur, I help technical minds turn their expertise into thriving businesses. Each week, I share raw insights on transforming engineering mindsets into business success - from crafting memorable introductions to winning premium clients. No corporate jargon, no "fake it till you make it" - just real experiences and proven approaches for engineers ready to grow beyond their technical roots.

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