Creating a strategy that wins for you

A story, a framework and a prompt you can use.


On my run yesterday I saw a mongoose.

I grew up on the East Coast of the USA, so I’m very used to seeing squirrels, chipmunks, rabbits — but never a mongoose.

But now that I live in Okinawa Japan I see them fairly often.

The mongoose in Okinawa is a good example a bad strategy with great execution. It’s a recipe for disaster.

Today’s newsletter is going to be about picking the right strategy to help you win and avoid failure.

The Simple Strategy

To create a strategy that helps you win and build a wonderful life

- Start with constraints.

- Then move to goals.

- Then strengths.

The strategy should use your strengths to hit your goals and avoid the constraints.


In 1910, 17 mongoose were released into the main island of Okinawa. They were brought in from India, in an effort to control the very poisonous Habu snake.

The Habu has a lethal bite and often injured farmers who accidentally stepped near it. The Indian mongoose is well known for it’s ability to fight and kill venomous snakes. They’re feisty little critters and have a strong resistance to snake venoms. They actually hunt cobras, which is kind of insane.

The mongoose looked like the perfect answer to the Habu problem. Eat the snakes, look cool doing it, everyone is happy. Right?

In the 100 years since introduction, that population of 17 mongooses (mongeese?) has really taken hold in Okinawa and there are now thousands on the island.

Mr. Mongoose eating a cobra.

So how did they do with the Habu?

They’ve done terribly, because the Habu is awake at night and the mongoose is awake during the day! They aren’t thought to interact at all!

Instead, the mongoose eats other small animals. Like the now critically endangered Okinawa Rail.

The Okinawa Rail

The execution of the mongoose strategy was excellent.

But it was the wrong strategy.

Why it matters

This is what we want to avoid in your business. We do not want the wrong strategy, well executed. That will eat your life. I’ve seen too many peers who “won” the game of business and lost their marriage, or relationship with their kids. I don’t want that for anyone.

Instead, we want to you have a strategy that:

  1. Navigates your constraints

  2. Helps you achieve your goals

  3. Takes advantage of your strengths.

That’s a tall order! But it’s possible. You’ll have to get creative and be ready to identify what you are and are not willing to do.

I did this very process when we moved to Okinawa from Virginia for my wife’s work. I had to basically start from scratch for my work.

  • My product-driven side hustle wasn’t in a place for me to pull a salary.

  • I couldn’t use any of the venture-backed start ups I had networked with.

  • Radically different time zones meant I couldn’t go back to management consulting.

Technically, I could have chosen one of those other options — and flown back to the states for work, or turned nocturnal — but both of those would have wrecked my family life. We have six little kids and they need my time. I was not willing to do that.

So instead I went:

constraint → goals → strengths → strategy.

How it works.

To help you define success for you and create a strategy to get there, here are the exact questions that I asked. I also use these with my coaching clients.

It’s often easier to say what we don’t want than what we do, so I start in the negative. You want to outline your non-negotiables, or constraints first.

Constraints: What is NOT Ideal?

These are your constraints. This is the step they missed in introducing the mongoose. They failed to add a constraint of “not eating the local wildlife.”

  • NOT Ideal Work Time

    • When can you NOT work?

    • When should you NOT be thinking about work?

  • NOT Ideal Revenue

    • What are you ready to be done with financially?

    • What number would you say NO to, to keep with your vision and values for your business or self?

  • NOT Ideal Work Activity

    • What have you worked on in the past but do NOT want to do in the future?

    • Who have you worked with in the past but do NOT want to work with?

Goals: What is Ideal?

Let’s switch to the positives. These are your goals.

  • Ideal Work Activity

    • What are you working on?

    • When have you worked and forgotten to look at the clock, time just flew by?

    • Who are you working with?

      • What are your co-workers and clients like?

  • Ideal Work Time

    • When are you working?

  • Ideal Revenue

    • What is your ideal personal monthly revenue? (Owner draw or salary)

    • What is your ideal business monthly revenue?

Once you’ve written these out, sit with them for a little while. It can take time for us to be really honest with ourselves. It took me a few weeks to realize that I was ready to give up working hours in the afternoon to be flexible to pick up my kids from school.

Strengths: What are you good at and love to do?

Then, we move to your strengths. This only takes two questions.

  1. If you were in a room with 1,000 random people, what situation or topic would make you the most knowledgeable or skilled person there?

  2. What project would you do for free because you love it so much?

Now we know what we cannot do (or are not willing to do), what we are aiming at (not what someone else thinks we should) and what unique strengths we have. That’s a great start to creating a good strategy!

How to create the strategy.

When it comes to actually creating the strategy, you need three things.

  1. Distribution - you have to find leads

  2. Cashflow - you have to turn leads into sales consistently

  3. Optimization - you need to get many at-bats to continue to improve your process, lower your expenses and increase your value.

Start with the constraints, goals and strengths you outlined above. Then add in distribution, cashflow and continuous optimization. You’ll be unstoppable.

A Prompt You Can Use

If you’re stuck on brainstorming a strategy, try this prompt. To use it prompt, replace the [bracketed] text with the answers you provided above. Copy and paste it into ChatGPT 4.0 or Claude Opus for the best possible answers. You can also try it with any LLM and see what response you get!

“ChatGPT, I need to develop a strategy that aligns with my personal and professional goals, leveraging my unique strengths and respecting my constraints. Here's what I've identified so far:

  • Constraints (Non-Negotiables): [List of constraints such as times you cannot work, financial limits, types of work or clients you want to avoid]

  • Goals (Ideal Outcomes): [List of what you are working towards, including type of work, work environment, revenue goals]

  • Strengths (Personal Advantages): [List of your key skills, resources, and personal traits that give you an edge]

Could you help me create a strategy that integrates these elements effectively, ensuring I avoid the common pitfalls that lead to personal and professional dissatisfaction?”

Try it out. Let me know how it goes!

I want you to win and I want you to have a joyful life to the full.

I want you to have a strategy that works for you!

Catch you next week!


Whenever you’re ready, I help bootstrapped entrepreneurs increase their profit in two ways.

  1. If you need help crafting your strategy, the 1-hour 1-on-1 might be right for you. These are best for businesses or entrepreneurs in the launch stage, usually under $200k in revenue. It’s amazing how much we can get done in an hour.

    Book your call here.

  2. Make your business more profitable, peaceful and resilient with Simple Strategies Coaching. A cross between coaching and consulting, it includes 2 major deliverables and 12 weeks of 1-on-1 coaching with Nate. These are best for more complicated businesses that are scaling, usually between $200k and $1.5M.

    Book a call here. 

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