3 Reasons Why Entrepreneurs Feel Overwhelmed

Here's How You Can Get Out Of It

I came across a recent study on small business owners—40% reported experiencing burnout.

Another one—25% of businesses fail in their first year, 50% within their first 5 years.

Even if the numbers aren’t 100% accurate, this still speaks to a pandemic in entrepreneurship.

“The graveyard is the richest place on earth, because it is here that you will find all the hopes and dreams that were never fulfilled, the books that were never written, the songs that were never sung, the inventions that were never shared, the cures that were never discovered, all because someone was too afraid to take that first step, keep with the problem, or determined to carry out their dream.”

Les Brown

The Root Of Overwhelm

Over my 5 year journey working with coaches and creators, I’ve seen many entrepreneurs burn out.

There are 3 reasons, at the core, why entrepreneurs feel overwhelmed:

  1. Lack of Alignment

  2. Lack of Focus

  3. Lack of Predictability

All leading to a self-sabotaging, yet addictive, pattern of overthinking.

Entrepreneurs are addicted to chaos and have a love-hate relationship with overthinking.

Thinking and problem solving is our superpower… until it’s not. And we’re creating problems that aren’t actually problems. Overthinking turns to overwhelm. Overwhelm leads to burnout.

Our greatest gifts can also be our greatest obstacles.

When we’re overthinking, what we really want is clarity.

And when you look even deeper, what we truly want is certainty (security and safety). “I’ll take action when I KNOW for certain I’ll get what I expect. I’ll start when I know the RIGHT way to start.”

But the reality is there’s no such thing as absolute certainty.

What we should be building for is not certainty, but predictability.

Predictability: consistent repetition of a state, course of action, behavior, or the like, making it possible to know in advance what to expect.

Predictability provides data and fuel for clarity. If we reverse engineer clarity, it looks something like this:

Aligned and focused action > consistency > predictability > clarity

Even if you take action and it consistently doesn’t produce the results you want. That still creates predictability: data on what to do or not do next.

30 outreach messages a day that doesn’t work tells you that your outreach message is not compelling enough to create a response. Optimize your message and keep going.

What doesn’t create clarity… is overthinking and not making decisions or taking action.

I know, common sense right? But common sense doesn’t always mean common practice.

So the question is: how do you make it a common practice to create predictability through consistent and effective decision making and focused action?


  • Systems create Leverage.

  • Leverage creates Margin.

  • Margin is the space within where you get to keep growing, in business and life.

The name of the game: design your business operating systems to prevent the 3 core reasons that create overwhelm and overthinking.

Reason 1: Lack of Alignment

Clarity on deciding what to do begins with knowing what you truly want, then aligning everything to that.

The first question I ask all my coaching clients: “what you do truly want”. It’s surprising but most entrepreneurs, even the ones with 7-figure businesses, struggle with clearly articulating what they truly want.

You can’t create alignment if you don’t have a North Star (vision, values, goals) to align everything to.

If you do know your north star, then alignment is simply a matter of congruence. A lack of congruence looks like:

  • Working on something that’s not aligned with your vision and goals

  • Working on something that’s not aligned with your values and principles

  • Your work was aligned but it changed directions and is no longer aligned with your vision

  • Your vision or values changed and what you’re currently working on is no longer aligned

As simple as this sounds, it requires asking yourself hard questions and being radically honest with yourself.

How To Create Alignment

Step 1: Create a clear North Star

A great place to start is by creating what I call your Strategic Vision.

  • Get clear on your 10 Year Visionpersonal and business must align

  • Get clear on your 3 Year Milestonespersonal and business must align

  • Get clear on your Core Focuswhy your business exists in this world

  • Get clear on your Core Valuesthe standard you build and hold your team of A-Players to

  • Get clear on your 1 Year Goalsyour priorities and commitments, not aspirations. Make them clear, tangible, and achievable

Need help with this, check out my free Strategic Vision Planner.

Then create a 1-page Strategic Vision. Make sure everyone on your team is aligned and has a copy. As the founder and visionary, I review my Strategic Vision every morning and I encourage my teams to do the same.

The clearer the vision and goals, the easier it is to make better decisions and take aligned action.

Step 2: Design your operating system for aligned Decision Making

Your Strategic Vision is now a decision making filter.

Make it a common practice that you and your team run all big decisions through the filter. When something is not in alignment, you give yourself and your team permission to let go of it. Make the “no”, “not now”, and “here’s why…” easy.

A clear vision creates a decision making system that eliminates overthinking and over-discussion.

Step 3: Review and realign your Vision, Goals, and Systems frequently

I remind my clients over and over that vision setting is not a one-and-done thing.

Things change and evolve in each season of your business and life. You need to check in on congruence frequently and be relentless with letting go and realigning.

When there’s alignment to your vision and goals, there’s no time and space for overthinking.

Reason 2: Lack of Focus

Most people think Productivity is about getting more done.

Productivity is actually about getting the right things done—while enjoying your time working towards your outcomes. That means knowing clearly what your priorities are and managing your time and energy around them.

Most people confuse activity with productivity.

Productivity is the byproduct of well designed systems for focus and joy. There are 2 operating systems you need on both the individual and team level:

  1. System for Prioritization

  2. System for Problem Solving

“You do not rise to the level of your goals. You fall to the level of your systems.”

James Clear

Let’s tackle each one.

1. System for Prioritization

There are 3 problems I see entrepreneurs make when it comes to prioritization:

  • Not knowing what your priorities are

  • Not separating what’s important from what’s urgent

  • Having too many priorities where everything feels important

Build an operating system where priorities and accountability are so clear your team has no space for overthinking.

Here’s what you can do…

Step 1: Create clear Quarterly Outcomes

Clear means less overthinking and more focused execution.

  • Create quarterly outcomes that align to your 1 Year Goals. Use a consistent framework. I like OKRs.

  • Assign clear responsibility and accountability

  • Do this every quarter rigorously—review, plan, align

I’ll share my Quarterly Planning process I take my teams and clients’ teams through in a future letter.

Step 2: Map out and Time Block your week

Show me your calendar and I can tell you what you’re really prioritizing.

  • Create time blocks for Deep Work and your priorities and goals

  • Add time blocks for Rest & Recovery (you’re either prioritizing rest or you’re not)

  • Add time blocks for Creative and Strategic Thinking (different from overthinking)

  • Time block everything else that’s important to you (family time, health, social…)

What you prioritize and how you prioritize it shows what you’re really committed to.

Step 3: Set up systems for accountability

  • Run effective weekly meetings to review progress on your quarterly outcomes and goals

  • Run effective 1:1’s with your team members and teach your managers how to run them

  • Be relentless with saying no (or not now) to most things outside your priorities

Productivity is not getting more done, it’s getting the right things done and enjoying your time working towards your outcomes.

“To me, ‘busy’ implies that the person is out of control of their life.”

Derek Sivers

2. System for Problem Solving

I noticed a game-changing pattern when coaching my clients and their teams.

How quickly and sustainably a business grew correlated to how quickly and effectively their team solved problems and made decisions. Specifically, the ones related to their priorities and goals. The winning teams had one thing in common: a system for problem solving.

Here’s a system I use:

Step 1: Create a central database to submit and track problems

If people don’t know where to go with their problems and issues…

They go inwards and spin their gears.

Dedicate a single place for your Problems List—notion, google sheets, whatever platform you want to use (just not your Slack)

Step 2: Create a process and template for submitting problems.

A standard process for problem solving leaves more time and energy for making decisions and focused execution.

Create a Proposed Problem document template for your people to submit problems.

When someone submits a problem, the document should include:

  • What’s the problem?

  • How they contributed to the problem? (practicing radical responsibility)

  • A proposed solution

  • A quick 2 min loom video providing context

This trains your team to be proactive problem solvers, rather than reactive ones.

Step 3: Encourage quick and effective collaboration when solving problems

All relevant team members can contribute to the problem solving by reviewing the Proposed Problem document.

  • If they agree with the proposed solution, they can sign off on it

  • If they don’t agree, they can add their own suggested solution or comment

Step 4: All problems should have a dedicated Decision Maker

Once all relevant team members have contributed to the problem solving…

The pre-assigned Decision Maker will:

  • Review the doc and ask qualifying questions if needed

  • If they have what they need to call the shot, they call it

  • Write out the Decided Solution and clear actions

All of this can happen quickly and effectively in written format before needing to call any meeting.

This will cut down 80% of meetings. Most decisions don’t need meetings. Save time and energy for productive work.

Systems create leverage.

Leverage creates margin.

If you need help with any of this (systems, templates, training), consider checking out my Lean Biz OS course.

Reason 3: Lack of Predictability

This one is usually the byproduct of the first 2 reasons.

The lack of predictability in our business makes it hard to make faster and better decisions, leading to inconsistent or unaligned actions.

  • Unpredictable revenue

  • Unpredictable profit

  • Unpredictable client results

  • Unpredictable labor efficiency

While you can’t create absolute certainty, you can get better at making decisions and taking massive action… engineering data for predictability.

There are 3 core operating systems (OS) in your business you want to design skillfully to increase predictability.

System 1: Your Team OS

We covered a lot of this above.

  • Clear Goals and Quarterly Outcomes (priorities)

  • Clear role Responsibilities and Accountability

  • Clear process for Solving Problems

  • Clear process for Making Decisions

Most people think labor efficiency is a skills thing. If I have smarter and more experienced A-Players, my labor efficiency and team productivity will go up.

It can… but what I found to be more important than skill and competence is your team’s ability to make faster and better decisions; focused and consistent actions.

System 2: Your Growth OS

Predictable growth is better than fast and exponential growth.

You’ll hear stories of entrepreneurs who scaled too quickly and amidst the overwhelm, had to sacrifice parts of the business (or themselves) to upkeep. You won’t hear stories of entrepreneurs who predictably and sustainably grew their businesses and had to scale down.

This is why I think “scaling” is overrated.

Predictable growth that leaves margin for the entrepreneur (and their team) to enjoy their lives is way more exciting.

What needs to be well designed in your Growth Operating System:

  • Products or offers that generate predictable revenue (think monthly recurring revenue)

  • Clear process for Audience Building

  • Clear process for Demonstrating Value

  • Clear process for Monetizing

This is how you stay sane without overthinking every month how you’re going to create enough revenue to upkeep your business.

System 3: Your Fulfillment OS

If you don’t have a system for delivering consistent and predictable results for your customers…

You don’t have a business. You just have a good marketing and sales strategy.

I’ve coached entrepreneurs with amazing marketing and sales strategies but subpar products. Unsustainable. The moment their marketing stops working, they go into overwhelm.

Design great products or offers and even better delivery systems. Focus on creating consistent results, happy customers, and high retention.

What to design skillfully in your Fulfillment OS:

  • A rockstar customer Onboarding Experience

  • Clear process towards Results (bonus: shorten the time to results)

  • Clear process for them to keep leveling up with you (think ascension)

This creates the predictability and leverage to be experimental (and not reliant) on your marketing strategy.

Better Decision Making and Focused Action

TL;DR if you skipped to here.

There are 3 reasons why entrepreneurs burn out from overthinking and overwhelm:

  1. Lack of Alignment

  2. Lack of Focus

  3. Lack of Predictability

The solution to prevent overthinking—create better systems for:

  • Making aligned decisions

  • Solving problems

  • Taking massive focused action

Better decision making and focused action creates predictability.

Predictability prevents overwhelm caused by uncertainty and lack of clarity.

That is it for today!

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Let’s keep winning together!

Your Pal,


P.S. Whenever you’re ready, there are 3 ways I can help you:

  1. Check out resources, templates, and courses I’ve created on building better systems for business

  2. Want my help with building a lean and profitable business that lets you enjoy your life? I offer coaching

  3. I share insights and tips on Twitter, Instagram, and LinkedIn. Follow me and say hi!