How Entrepreneurs Can Prioritize, Plan and Progress Effectively

I’m the kind of observant human who gets itchy fingers the second I encounter something that could work better. I have an inherent desire to optimize all things — and I’m not alone.

Entrepreneurs are attuned to translating the problems of self & others into opportunities to build.

Betterment is an integral attitude to how a Founder’s mind functions in work and life. But for some reason, there are little-known approaches to how entrepreneurs master managing multiple projects of increasing complexity.

So I built a framework I’d like to share with you.

This is how I prioritize, plan, and progress.

Let’s get practical.

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1. Prioritising winning ideas

As an idea person, I struggle with capturing ideas that matter and often misdirect my energy toward the ones that don’t have a long-term impact. It wasn’t until I stumbled upon Hyperfocus by Chris Bailey and this quote that I was able to turn my scattered digital life around:

“Your mind is for having ideas, not holding them.” — David Allen.

I quickly formed the habit of writing down ideas to avoid filling my limited attentional space with trivial things. Then, I iterate and add layers whenever I can. This way, my brain is wired for creative output, not database storage. And if computers are better for the latter, why not free your mind from holding ideas and channel your energy into creating something new?

I use a framework called ICE, which automatically calculates and ranks my ideas across 3 metrics:

• Impact (1–10) → How big is the potential impact of the idea?
• Confidence (1–10) → How confident are you for this idea to work?
• Ease (1–10) → How easy is it to implement?

= ICE Ranking (all multiplied)

Packaging this into a Notion template helps me gather, rank & prioritize ideas so that I can focus on the right ones at the right time. Get it for free.

Your attentional space is precious.

Don’t wait to write down ideas.

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2. Planning from macro to micro

I learned a lot during my running OFC. Managing a multi-disciplinary team remotely taught me that plans and human resource distribution rarely aligned with our initial intentions. People aren’t machines — we have bad days, deliver sub-par work, and can’t always operate at our best selves. Even when planning with this in mind, there are still hundreds of unexpected things that can pop up and suddenly invalidate plans.

I quickly noticed that following through with plans needed a balance between loose planning and a limited task load. Not accounting for high variability and still expecting quality output will always misfire.

This is a system that works best for solo or small teams of less than 5 people. Once you exceed this team size, SCRUM and Agile methodologies might serve you much better than the Bootstrappers Plan:

1. 30–60–90 day plan » 3 actionable goals for each month.
2. 3–5 weekly TIDOs » Tasks w. Intentions & Desired Outcomes.
3. Implementation Intention using a chosen Calendar.
4. Analog daily tasks on how to reach your TIDOs.

As you can see, the four steps guide you from the macro big picture down to a micro execution level. Starting with your 30–60–90 day plan and using TIDOs to break these down into weekly macros will help you achieve smaller tasks that have a tangible, long-term purpose. Here is an example TIDO from a free template you can grab here.

The goal here is to avoid overproducing and committing to outdated todos. Instead, you use a system designed for generating macro momentum, week by week, while keeping everything in line with your monthly goals.

I use this system for planning daily and weekly, but it doesn’t have to work for everyone. So if there is anything you take away from this, start thinking about macro and micro-level desired outcomes.

Need a pre-built system? Check out CREATOR OS.

Optimize for loose plans that feel light.

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3. Progress from regular retrospectives

Progressing is only half of the rent if you can’t reflect on what you did and collect learnings to inform a better path forward. Even if your plans might align perfectly from macro to micro, you won’t be able to improve the quality of output if you don’t reflect honestly on what has been achieved. Good documentation is the core driver for retros to uncover the quality of each week’s momentum.

Once you begin planning weekly, it’s only fitting to do retros at the same frequency. I prefer to use Sundays for this. In CREATOR OS, I build a system tying everything together to cover 4 areas:

• Personal Relationship Manager activity status.
• If you are running a monkmode, reflect on your Do’s & Dont’s.
• The % completion & accuracy of plans from your weekly TIDOs.
• How the completed TIDOs align with your 30–60–90 day plans + one thing that went well & one thing that could be better.
• Overall progress satisfaction /10.

Executing and tracking regular retrospectives over weeks and months will give you a clear picture of the quality of progress you are achieving. Plus, you can easily spot areas for improvement if you watch closely.

Retrospectives = Reflection, which helps pick apart complex experiences to uncover learning opportunities for growth.

Progress without reflection is misguided.

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Next steps

The last thing you want is to overwork yourself and execute tasks that have no value to your short & long-term life goals. In a world where work is increasingly multi-faceted, entrepreneurs have an orderly duty to stay on top of things with a purposeful system that bridges prioritization → planning → progress.

Not owning or creating this for yourself will result in playing the game of catchup and misdirected efforts.

I want to leave you with three questions:

1. What system will you use to prioritize ideas that matter?
2. How can you consistently plan from macro to micro?
3. What areas will you do regular retrospectives over?

This read was crafted for the bootstrap.supply ecosystem.

See you around on Twitter.