Every Strength Creates a Hidden Struggle
Your hidden struggle is the price you pay for your strength. Every strength has a price. Nobody gets one for free.
Every strength creates a hidden struggle. It is like two sides of the same coin.
You cannot have a coin where you only have heads or tails. What makes a coin is that it has two sides.
Similarly, I have observed that our greatest strengths as entrepreneurs also give birth to our greatest struggles. And I want to be precise about what I mean by that, because it is easy to hear this as “every strength has a downside” and move straight past it. What I actually mean is that the struggle is the price you pay for the strength. Every strength has a price. Nobody gets one for free.
Let me explain.
One of my biggest strengths is to be able to seek perfection in what I do. It is my desire and obsession to create something of the highest quality that motivates me. But as a result I find myself iterating on something for the nth time when I actually should be getting it out. And if you look closely at what is happening there, the part of me that refuses to accept good enough is the exact same part that will not let me call something finished. It is not two separate traits, one good and one bad. It is one trait, doing its job in both directions.
Another client of mine, a serial entrepreneur, is crazy good with big picture thinking. Thinking of multiple ideas that are exponentially bigger than anyone he knows is what inspires him. But his hidden struggle is that this often gets him overwhelmed. Same mechanism again. A mind that can dream up ten possibilities at once also has to hold those ten possibilities at once. The dreaming big and the overwhelm are not two different things happening to him. They are two sides of the same coin.
Yesterday I was on a call with another client who has been the MD of multiple large organisations. When I was trying to understand his leadership style, he said it was simple. Care for people so deeply that they are rooting for you.
Helping others was his leadership strength, but his biggest struggle was asking others to help him.
He has spent thirty years being the person everybody else leans on, which means he has had almost no practice at asking for help when he is the one who needs it.
Over the years I have watched the same handful of these coins show up again and again in the people I work with. Here are seven of them.
The 7 Hidden Struggles of the Most Successful
You are a big thinker
But you are often overwhelmed
You are future focused
But you are not fully present
You seek perfection
But you do not see your own progress
You love helping others
But you find it hard to ask for help
You are driven to succeed in one area
But it costs you the other areas of your life
You inspire people all the time
And yet you feel lonely sometimes
You are wired for action
But what you truly crave is creative reflection
Your Blind Spot
Nobody ever tells you what your strength costs.
Most business books will tell you about zoning in on your strength and your unique ability. But very few will bring out the blind spot hidden underneath it, which is that your hidden struggle is born out of that exact strength.
And there is a good reason you cannot see it. Everyone around you praises the strength. It is the thing people thank you for, hire you for, and remember you for. Nobody sends you the bill for the other side of it. So you keep paying that bill quietly, year after year, without ever stopping to ask whether the amount is reasonable.
That is what makes it so expensive. Your hidden struggle does not cost you once. It costs you over and over, for years. The thing that never ships. The quarter that gets away from you. The help you needed and never asked for.
The good news is that a hidden struggle only has power over you as long as it stays hidden.
“Knowing what success costs you is what stops you succeeding at something that makes you miserable.”
Coach Sid
Do This To Fix Your Blind Spot
First, find the struggle.
Ask yourself one question.
What is the opposite of my greatest strength?
If you are great at seeing the big picture, the opposite is narrowing down to one thing. If you are always looking ahead, the opposite is being here now. If you are the one who helps everybody, the opposite is asking somebody for help.
Whatever that opposite is, you have probably not done it properly in years. That is the price.
And if you still cannot see it, ask the person who works closest to you. They have been watching it happen for years and they will tell you in about ten seconds.
Then build one constraint.
You are not trying to get rid of the strength. That would mean giving away the best thing you have. And you are not going to stop paying the price either. What you can decide is how much you pay.
A constraint is how you decide. It is one rule you set in advance, while you are thinking clearly, so that you do not have to catch yourself in the moment. And you will not catch yourself in the moment. That is what makes this a blind spot in the first place.
So the rule does the noticing for you. Every time you bump into it, you see the thing you would otherwise have walked straight past.
In my own case, one of the rules of thumb I apply to overcome my need for perfection is the 80% rule. Whenever I need to create something, I work on finishing the first 80 percent of it in the fastest possible way, and get it out for feedback after. I know that if I wait to make it 100 percent, it is probably never going to happen. And odds are I would never be able to accurately predict that final 20 percent on my own anyway. This is a stopping rule. Its whole job is to tell me when to take my hands off.
Similarly, when I am coaching my client who is the serial entrepreneur and big thinker, I consciously create constraints so that his mind can think big without the overwhelm. Constraints like working on a maximum of three ideas at a time, and working in 90 day timeframes. This is a cap. It does not make him think smaller. It gives his thinking edges.
And for the leader who gives far more than he asks, the constraint has to run in the opposite direction. One ask a week. Name one thing he needs, and take it to one person either on his team or on his personal board of advisors. This is a minimum, because his strength does not need slowing down. It needs a floor underneath the thing he never does.
I should also say that none of these constraints are easy to live with. The 80% rule means some of my work goes out into the world less polished than it could have been, and I have made my peace with that, because I decided it is a better price than work that never goes out at all. That is the real tradeoff. You either make it deliberately, or your strength keeps making it for you.
The whole thing on one page
- 01Name your greatest strength. The thing people come to you for. The thing that gives you energy rather than taking it away.
- 02Ask what the opposite is. What is the opposite of that strength? Whatever it is, you have probably not done it in years. That is the price.
- 03Build one constraint. A stopping rule if it does not know when to stop. A cap if it wants everything at once. A minimum if it never does the thing at all.
- 04Say it out loud to one person. It is much harder for a struggle to stay hidden once somebody else knows about it.
So what is your greatest strength as an entrepreneur? And what is the struggle hiding underneath it that you have been paying for?
Coach Sid
The Founder’s Bottleneck Audit
Ten minutes to find out which of these is actually costing you the most right now.
A free 10-question audit for scaling founders and next-gen leaders. The same questions I ask in a first coaching session, so you know what is really holding the business back rather than guessing at it.
- 10 questions that surface the pattern costing you most
- A personalised result with your top three blind spots
- One concrete shift you can make this week