THE LIFESTYLE ENTREPRENEUR

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Delegating

Delegation is an essential skill for anyone who wants their value to grow over time.

It’s not just for entrepreneurs—it’s for every career path:

• Attorneys need to delegate to grow their book of clients and make partner.

• Solopreneurs need to hand off low-leverage work to focus on delivering value.

• Real estate agents need to offload admin to scale their commissions.

And yet, most people struggle with delegation. In the entrepreneurial world especially, it’s one of the biggest bottlenecks to growth.

• There are 33.2 million small businesses in the US.

• 98% have fewer than 100 employees.

• 89% have fewer than 20.

• The median small business owner earns ~$50K per year.

A big reason? People problems.

And within those people problems? An inability to delegate and elevate.

The Delegate and Elevate Tool

This simple 2x2 tool, created by Gino Wickman, helps clarify what you’re doing—and what you shouldn’t be doing anymore.

Step 1: List everything you do.

Step 2: Estimate how long each task takes.

Step 3: Subtract from your available weekly hours.

Step 4: What’s left is what needs to go.

Then place each task in a quadrant:

• Bottom right – Don’t like + not good at → delegate ASAP

• Bottom left – Don’t like but good at → delegate soon

• Top right – Like and good at → evaluate if this scales

• Top left – Love and great at → protect this with your life

The magic happens in the bottom half. That’s where your energy is leaking and your company is being held back.

Delegation Isn’t Just to People

You can delegate by:

• Handing off to a team member

• Automating the task

• Simplifying the process

• Eliminating the task entirely

Most people don’t even get to the point of clearly seeing what’s on their plate. But going through this exercise quarterly changes everything.

My Experience

I’ve built and run companies from 0 to 100 employees.

I’ve done delegation well.

I’ve also done it poorly.

You usually don’t notice the difference right away, but over time it shows up in retention, frustration, and results.

In my last startup—Wandertest—we grew from 0 to 25 employees and $5M in revenue in less than a year. Delegation was key. My role moved from owning every seat to focusing on just visionary and marketing in 6 months.

That only happened because of deliberate delegation.

My Current Delegation Work

I'm in my second year as a full-time business coach, and here’s where I’m at now:

• I had a full-time assistant for almost a year, and decided to start over in February. Since then I’ve been running everything myself to evaluate my processes, before bringing on a new assistant.

• During this time my focus has been to identify and execute the core work to create a full coaching practice. That has allowed me to eliminate many tasks I was doing every week when I had a teammember.

• Additionally since AI has changed things so rapidly, I’m working hard to establish which processes can be automated or enhanced with AI tools.

• One of my rocks is to hire a new assistant this quarter - by the end of July my goal is to have someone hired, onboarded, and 80% delegated

• I’ve also reduced my content creation to it’s bare essentials (3-5 LinkedIn posts per week). I plan on bringing on part-time content support the following quarter

My cadence for this is still once per quarter. It’s not about huge change—it’s about steady progress. One task delegated per quarter makes a big difference over time.

If you haven’t used the Delegate and Elevate Tool yet, here’s your invitation. It takes 30 minutes, and it might unlock the next level of your career or business.

Talk to you next week,

Mike