How to Create the Freedom Every Founder Craves

Written by Dave Bailey

Filed under founders management meetings


Many founders feel trapped in their own ventures, searching for freedom. This strategy will help you regain control and find that entrepreneurial freedom you once dreamed of.

When you ask most founders why they started their business, you’ll hear the answer they’ve been conditioned to provide: “I always wanted to solve this big problem”.

However, there’s a more personal reason entrepreneurs build businesses that’s less acknowledged.

Most founders start businesses to achieve freedom.

Before becoming an entrepreneur, I spent a few years as a management consultant with one of the top firms. I was better paid than all my friends—but it felt like a prison. I had no say in where I spent my time, who I worked with, and whom I served.

I left consulting to found a business, dreaming of the day when I had complete control over my time. But as my business scaled, I started to feel trapped in the role I’d created for myself.

Sound familiar?

If you’re a founder who feels trapped by your business, you aren’t alone. I coach some of the world’s most elite founder CEOs who, behind the scenes, wrestle with this very situation.

Indeed, I have found myself in this situation multiple times; attending meeting after meeting with a smile, while secretly feeling miserable.

But the key is to realise that this feeling is like one of Apple’s awful alarm sounds: it’s job isn’t to make you feel good, it’s to force you to wake up and get out of bed.

The great unshackling

I’ve developed a method of helping founders to free themselves from the invisible forces that bind them to a life they hate—and evolve into better leaders in the process. It’s led to huge breakthroughs with all sorts of CEOs, and it can help you uncover deep insights about your life.

That said, you need to be an entrepreneur to experience its full benefit. Unlike entrepreneurs who trade security for freedom, employees trade their freedom for security, and therefore don’t have the leeway to implement this fully.

Step 1: Clarify your short-term objectives (not the company’s)

It’s easy to confuse the company’s objectives with the CEO’s. However, the difference is critical. When you conflate the company’s objectives with your own, you’re likely to think every problem in the company is your project. You’ll jump in to fix your team’s problems—and your time will disappear.

Here are some examples to illustrate the difference between company and CEO priorities:

  • Company objective: to achieve 3X growth
  • CEO objective: to set the company objective
  • Company objective: to launch a new capability by Q4
  • CEO objective: to hire a new product leader

An effective way to uncover your objectives is to go through each of the meetings you attend and ask yourself: “what difference am I trying to make by attending this meeting?”.

While your objectives will be specific, they are likely to fit into one of these categories:

  1. Set the strategy and communicate it to all stakeholders
  2. Hire and retain a high-performing leadership team
  3. Ensure the business has enough cash

The clearer your objectives are versus the company objectives, the easier you’ll find it to achieve them more efficiently.

Step 2: If you could only work one day a week, how would you achieve these objectives?

This question forces clarity over what really moves the needle. The funny thing is most CEOs I ask this to quickly come up with a plausible answer:

“Well, I’d work on Mondays. I’d run a team meeting in the morning, followed by separate meetings with my sales, product and finance teams. I’d have to reduce the duration or frequency of my one-on-ones as I’d have less time. And everything else I could delegate.”

Achieving such a significant shift involves saying 'no' to a lot of other people’s priorities, including those of your team, investors, and other stakeholders. This can stir up a lot of emotions. However, there's a simple truth:

If you’re spending 80% of your time on other people’s priorities, you’re unlikely to make a dent in your own.

Of course, you’re probably thinking… what should I spend the other four days doing? Well…

Step 3: How do you want to be spending your time in five years?

You hear about the importance of long-term thinking in business, but the same holds true for individuals too. When you ask people how they want to spend time in the future, all the current problems and projects and minutia are instantly forgotten.

Surprisingly, I frequently hear answers like this to this question:

  • I want to take a more strategic role in the business
  • I want to spend time networking to set up an acquisition or IPO
  • I want to build my personal brand
  • I want more free time—to spend with my family, my hobbies and travelling
  • I want to invest in early-stage businesses and support other founders

Next, I ask them: “Will spending your time in this way make you a better leader?”

“Of course!” they respond, before giving me a lengthy explanation about how much more present, clear-headed and positive they’d be.

Well then… let’s not wait five years if you could be that leader in a few months!”

The ‘One-Day Transformation’

The One Day Transformation

What results from these thought experiments is a prototype of a new way of spending your time. You spend 20% of your time on what you currently do, and 80% of your time on a new set of activities that align with who you want to become.

Your calendar could look something like this:

  • Monday: working or your current objectives, far more efficiently
  • Tuesday–Thursday: working on what you’d otherwise work on in five years
  • Friday: spending time out of the business

Why take a day out of the business?

This idea doesn’t tend to land with early-stage founders who are in the first few years of their business, actively involved in operating the business, and love their job.

However, when you eventually crave freedom, remember this is a viable option.

Many of the later-stage founder CEOs I coach reach a stage where they can take a full day out of the business per week. Not only does it provide a renewable source of clarity, serendipity and connection, it meets their primal need for freedom.

Without experiencing this freedom, they’d otherwise be miserable and resent the company they built.

Working on the foundations

Distinguishing your objectives from the company’s and reflecting on your long-term goals will provide you with useful insights about how you want to spend your time. However, implementing the results requires you to first achieve the CEO’s three core priorities.

  1. You must define a clear strategy that can be communicated and executed by others
  2. You must hire exceptional direct reports capable of leading and executing the strategy
  3. You must ensure the business has enough cash to pay your costs

If you can achieve these priorities, then all others are likely to be someone else’s: namely, your direct reports. This includes getting your input on their work, responding to emails, and running 1-1s. Therefore, filling capability gaps on your leadership team is essential and cannot be delayed.

In addition, investing in a Chief of Staff to whom you can delegate a meaningful proportion of inbound priorities that slip through the gaps of your other direct reports is essential. This role will speed up your development as a leader by helping focus your attention on high-level issues and staying out of too much detail.

Working on the mindset

When I speak to some founders, their guilt about delegating or taking time out of the business is palpable.

They make up all sorts of disabling narratives about why this is impossible, unfounded, or unrealistic—at least for their ‘unique’ situation:

  • “If you’re not driving the team every day, you’ll send the wrong message”
  • “The team aren’t strong enough without your support”
  • “Taking time out of the business is self-indulgent”
  • “If your investors find out you have free time, they’d fire you instantly”
  • “All your long-term priorities can wait, there’s urgent stuff to be done”

This is fear talking. It’s the invisible force that keeps you trapped in your current setup. In order to begin to overcome this fear, you’ll need to balance any unhelpful narrative that comes up with a more realistic (and kind) interpretation:

  • “The clarity, accountability and direction you provide the team sends the right message”
  • “If a teammate isn’t strong enough, they can’t be on the team—and that’s your priority”
  • “Taking time out of the business can provide you with valuable perspective”
  • “Your investors aren’t interested in time spent, they are interested in outcomes”
  • “There’ll always be urgent stuff, so starting on your long-term priorities is now or never”

You’ll often hear about the need for business owners to spend time ‘on’ the business. However, the only way to not work ‘in’ the business 24/7 is to work on yourself first.

Making your time count

If you want to reduce the amount of time you spend with the team, you need to make sure you're focused on the right things. Here are three pieces of advice to ensure your time with the team is put to best use:

1. Own Your Team Meetings

In contrast to 1-1s which serve your report’s needs, team meetings are there to serve yours.

When the team meeting serves you, you can serve the team—by providing the accountability, clarity and direction they need.

If you aren’t entirely satisfied by your team meeting, change it. No-one else will. At the end of the meeting, you should have the information you need to run the business effectively.

2. Set Up Accountability Structures

In its purest form accountability is ‘an ability to account for what’s happened’. Under this definition, any structure that provokes a leader to reflect and make commitments is a form of accountability.

Team retros, data reports and presentations can amplify the effects of accountability, even if you’re not there. CEOs often worry that data might take too long to collect… but that’s not your priority, it’s your team’s.

3. Hunt for Elevator Moments

‘Elevator Moments’ are the biggest impact a CEO can have in a meeting. These are the moments where the CEO helps their leaders to step out of the details and see the bigger picture.

“Let’s remind ourselves about what we’re really trying to achieve here…”

The interaction may take less than a minute, but has a greater impact than all the discussions about details and problems.

CEOs uniquely have the context to be able to do this, and spending time out of the business only makes this easier.

The door is already open

“The freedom we seek is always available”– Bruce Tift, author of Already Free

If you’re unhappy in your role, or you feel like you’re not growing as you could be, you’re probably spending 80% of your time in the wrong place. If you’re too loyal to the things that made you successful in the past, you can eventually become imprisoned by them.

By clarifying your long-term priorities and acting on them now, you can achieve far more than you ever imagined. You can become the leader you aspire to be sooner, deliver more results for your company, and enjoy the free time you so desperately desire.

The door is open. There’s no ball and chain. You’re already free.


Originally published on August 16, 2023.

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