It's Easy to Complicate Things

September 17, 2021

Back when I was performing as a guitarist in South Florida, I sometimes did session work on the side. One night, while playing on South Beach, I was approached by Brazilian singer Iramar and his producer to lay down some tracks on an upcoming album.

Recorded at Ocean VU Studio with Victor Di Persia at the helm, the album was released under the title: “é fácil complicar.” Translated: “It’s easy to complicate things.”

That phrase comes back to me when progress requires solving a key problem and unnecessary contraints need to be removed.

Often when we feel stuck or frustrated the answer is simple: we need to stop complicating things

Here are some common ways we overcomplicate.

1. We expect progress to unfold in a straight line

Sometimes moving forward requires significant changes (such as redesigning a product) or lateral changes, such as pivoting your business to something adjacent.

As an analogy, consider Mark Egan’s path. In the late 60s, he had already played trumpet professionally before moving to Miami to study at the University’s School of Music.

Egan brought his electric bass with him. He wasn’t nearly as accomplished on that instrument. But soon he was getting calls to do bass gigs. In an interview with Music in the Moment he explained:

More and more people called me because I had a good feel. I played one finger bass – and I mean on the fingerboard I really only played with one finger!

Demand for Egan’s bass playing grew. After he graduated and moved to New York City, the bass gigs kept coming: a gig with the Pointer Sisters, then with Eumir Deodato, then with David Sanborn, and so on.

This lateral shift unlocked a new future: Mark Egan went from being a trumpeter (and “one-finger” bassist) to being one of the world’s premier jazz bassists.

If you feel stuck in your business, why not explore a pivot to something related?


  • Would you rather architect than build?
  • Would you rather teach than manage?
  • Do you have strong diagnostic skills but dislike implementing related fixes?
  • Do you want to build once, sell twice? (Develop digital recurring revenue.)
  • Do you prefer fixing messes or taking something from good to excellent?
  • Do you want to investigate, research, or write?

Start compiling a list of your own thought-joggers. You’ll be surprised at the number of options available to you.

2. We’ve forgotten what we’re solving for

Sometimes when we set out to solve a key problem, we can get pulled off course by overthinking. We then wind up trying to solve a cluster of problems at the same time, with the most important one drowned in the mix.

This shows up as the placement of unnecessary hurdles to be cleared before the original problem can be solved.

Because circumstances are such that there is no moving forward with a perfect solution for the problem-cluster, we stay stuck.

I call this PIC - or problem identification creep. It’s similar to scope creep: a bloating of the work at hand. PIC bars progress and delays results.

  • Identifying problems worth solving requires clear thinking.
  • Coming up with solutions and ideas first, before identifying the core problem, creates new problems.

Staying focused on your most important problem(s) is key. Without this clarity, you may rush into action, wasting resources. Busyness may diffuse the psychic burden of a half-assed situation. But that burden will grow. And we may wind up discounting persistence.

So what can you do to avoid this scenario?

When the mental clutter starts accumulating, I simply stop and ask myself again: What problem am I trying to solve?

Everything snaps into focus. My options are clear. A decision follows quickly. The problem is resolved.

A few resources

Using a tool like this one can help you easily identify problems worth solving.

Good models can help you structure your thinking and solve problems constructively.

Some of my favorite marketing models are:

Startups might want to consider Strategyzer or for models and related online courses.

And then there are the excellent strategy resources from the founders of Blue Ocean Strategy: W. Chan Kim and Renée Mauborgne. At the core of Blue Ocean strategy is the creation of “uncontested market space” that “makes the competition irrelevant.”

Blue Ocean resources include:

Thanks to INSEAD, there's even a Blue Ocean Strategy Institute at Fontainebleau in France. The instutute offers distance and in-person programs on Blue Ocean strategy and Blue Ocean leadership.

3. Lack of process

Do you have a clear, written process for each major activity?

For example, for your email marketing, do you have clear goals, KPIs, and processes? Or are you randomly sending out “email blasts” when you feel like it?

A process is repeatable and clear. The KPIs provide a reliable measure of results and what needs improving. Improving a process often involves experimentation and small tweaks.

Well-chosen KPIs keep you on track, daily closing in your destination.

Implementing processes is simple. Executing them is a grind, but if the processes are sound, the grind is what produces results.

Some tough love: if you can’t describe what you’re doing in terms of processes, you don’t know what you’re doing. Writing produces clarity.

Documenting your processes also makes it easier to onboard new hires. And when it comes time to sell your digital properties, it can make those more valuable.

If you’re a solopreneur you might get away with not writing anything down. Maybe you’ve got it all in your head. But even solopreneurs can benefit from the clarity obtained by documenting processes.

4. Grind, but no think

The daily grinding on processes that work is essential to success. But so is taking time to think about the big picture and monitor KPIs.

I was recently reminded of this in my own work. We tripled the size of one team and I got caught up on the details associated with that, including the new flood of activity. I had to rearrange my schedule to ensure time to focus on the big picture thinking and KPIs at the beginning of each day.

Otherwise it’s too easy to get caught up in thousands of details and miss key opportunities for improvement or to miss indicators that something is slipping.

5. Focusing on gut instinct rather than evidence

Data is the only reliable steering system for your business. Knowing how to collect it and sift it; knowing what to ignore and pay attention to; is vital. And don't forget data's twin: experimentation.

Do you make decisions based on opinions or evidence?

While your intuition may open new avenues for creative exploration and testing, it can also be misleading. This is true in small everyday situations as well as in pivotal moments in a business.

Use data to check assumptions

Everyday example from my own work: During an offhand conversation the idea of boosting the throughout of our "P-Team" (an internal nickname) was raised. Someone floated the possibility of a bonus system as a possible means.

If we were the type of organization that made decisions off the cuff like this we might've moved forward immediately. But instead we check premises by looking at data. It took 5 minutes to see that week-over-week, the P-team was actually increasing their throughput.

The decision then became clear: while we still planned on implementing a bonus system, we needed to grow P-Team substanitally. We tripled the team's size in order to achieve the desired throughput.

Peter Reinhardt and Segment's search for product-market fit

Pivotal moment example: This example comes from Segment's journey to find the right product-market fit. Working within the framework of Y Combinator, their first product had failed. They had 6 months of funding left to find a direction.

A team member floated a new idea. "That is literally the worst idea I've ever heard," replied co-founder Peter Reinhardt, "I have no idea how you build a business around that."

In an interview with Y Combinator, Reinhardt recalled:

So we fought about it all day long - there were four of us - I was the most skeptical, I think. There was literally, like, brutal fighting.

I went home and I was trying to figure out how to kill the idea. I was awake half the night. Finally figured it out.

Reinhardt persuaded his team that they should create a landing page explaining the idea, with a sign-up form, and post it on Hacker News. Reinhardt knew no one would be interested. This seemed to be a good way to kill the idea. Soon everyone could get back to brainstorming.

After posting the landing page however, something unexpected happened. Interest exploded. The team had found their direction.

Fast-forward to 2020: after 9 years of rapid growth and success, Reinhardt and his co-founders sold Segment to Twilio for $3.2 billion.

Summing it up

Have you ever turned a molehill into a mountain? Snatched defeat from the jaws of victory? Refused to entertain opposing ideas?

Overcomplicating things can lead to completely avoidable problems.

We all do it. But the good news is, while it’s easy to complicate things it’s also easy to stop.