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Outsmart the Hustle

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Many entrepreneurs start out as a one-person show. They wear every hat, from bookkeeper and content creator to salesperson and head of customer service.

And in my experience, most business owners get so used to doing it all, even once the business is up and running, that they’re convinced they are the only one who can run the whole show.

But at some point, they will hit a ceiling. You can only work so hard and so long before you burn out and your business plateaus.

You’ll be tired, distracted, unproductive, and your creativity will plummet. On the personal side, weekends and family holidays, friends, and favorite activities will give way to work.

Does this sound familiar?

I call it being on the hustle hamster wheel. You think you’re the only one capable of showing up and getting the work done. The only problem with this is that you’re setting yourself up for trouble.

It doesn’t feel like it at first. Everything starts off with you being resourceful and taking care of business. You do it all – you create, you market, you sell, you deliver, and you support. Everything is going along nicely, assuming that you’re halfway good at all of the tasks listed above.

And then it happens. Slowly at first, you begin to realize that you’ve painted yourself into a corner. You’ve created the perfect job for yourself. If you don’t show up, you don’t get paid.

I call this the moment of awakening for many entrepreneurs. You realize that you’ve created a trap that you probably never intended to create. Your reward for bootstrapping a business is that you’re perpetually tied to it.

So, what’s the answer to operating a successful business and also recovering your personal time (i.e. your sanity)?

It’s called a Personal Free Day.

This is one of the most controversial, important, and non-obvious things I’ve learned as an entrepreneur. In my discussions with dozens of $1M+ service entrepreneurs, I discovered that many of them came to a turning point where they realized that the things that had gotten them to where they were, were the exact same things that were keeping them stuck there.

And for many, the thing that allowed them to escape the hustle of working so hard was a decision to construct their business around their desired life vs waiting until some abstract amount of money, clients, etc, was in place first.

Let me ask you a question.

How many times have you told yourself this? You’ve said something like, “As soon as I’m making $X per month, have X number of clients, get that big project done, then I’ll slow down.”

But here’s the little secret I’ve found out. Unless you start with the business structure you desire first, you’ll just keep chasing false promises.

I know this probably sounds unrealistic and completely backwards but just hang with me.

Dan Sullivan, Founder of Strategic Coach and one of my informal mentors, says that Free Days are the first step to entrepreneurial growth and success.

Dan says that, “In order to have high energy, to be focused on what’s most important, and to be creative in all your thinking, you must be well-rested and have a clear mind.”

I couldn’t agree more. Taking a Personal Free Day doesn’t happen when you’re exhausted, or even just tired. It happens when you’ve scheduled, planned, and protected your Personal Free Day so it truly is free – and then you actually take it.

Here’s how it works.

A Personal Free Day is a 24-hour day from midnight to midnight, where you take time off from work – no business-related activities like checking in with the office, no email or phone calls, not even business reading.

Personal Free Days are solely for activities that relax and rejuvenate you. For some people, it’s reading or going to a great movie and out for dinner. For others, it’s hiking or biking or a day at the spa.

Jill and I practicing our Personal Free Day(s) this week on Mt. Hood.

You can imagine that once you’ve got the hang of taking Personal Free Days, the natural result is that you’ll be more creative, more focused, more productive, more confident – and a whole lot happier.

But here’s the rub. Most of you won’t do it. Why do I know this? Because it’s counter intuitive to what you think you need to do.

A new approach.

A coaching client (let’s call her Sarah) operates a successful consulting business and she’s in high demand because she offers a very unique and valuable service to her clients.

While it looked like she was firing on all cylinders in her business, Sarah was feeling burned out from juggling a demanding travel schedule while trying to fit in regularly scheduled client meetings. She was constantly struggling with meeting the demands of her clients and needing to reschedule meetings all the time due to travel, and then feeling exhausted from it all.

This simply was not the best use of Sarah’s time or energy. When I asked her why she traveled so much, she answered “because that’s what consultants in my industry do.” But deep down she knew that this was not sustainable for her over the long-term. She knew that continued growth and happiness in her work could only happen if she was open to doing things differently and making Personal Free Days a priority.

Sarah knew she needed a change.

Is there a better way?

In our first coaching session together, we started to think about how Sarah could transform her current “overwhelmed” state.

We talked about her “ideal work week” and scheduling Personal Free Days away from work.

It took a bit of a shift in thinking, but the idea of building her business around her desired schedule left her feeling hopeful but also a little doubtful.

Sarah knew that her current way of working wasn’t going to work for her much longer. Yet she had never stopped to ask herself the question, “’Is there a better way to do this?”

Sarah had also noticed that some of the top people in her industry were more intentional about how they showed up in their businesses, including how they used their time. She made the decision that for the next 90 days she would only work with new clients virtually over Zoom.

Immediately, she was able to reduce her travel by 50% and increase her productively and happiness exponentially.

She also committed to taking two Personal Free Days every month.

Theory into practice.

Shortly after committing to taking two Personal Free Days per month, Sarah planned a trip to Los Angeles with her sister to celebrate her birthday.

“I felt that I was getting pretty good at keeping my Personal Free Days separate from my work days. And everything was going well until I decided I was going to make one work call. Just one call. What could go wrong? Well, it ruined the whole day – for both me and my sister. I was upset by the call. My sister was mad at me. Luckily, we salvaged the day in L.A. and the call didn’t ruin everything. But I remember thinking, ‘Wow, that was only one phone call. How could that possibly happen?’ Well, I broke the rule. It was a hard but valuable lesson.”

Practice makes perfect.

When Sarah told me her story, I congratulated her for setting her trip up to have great Personal Free Days, but Sarah made a common mistake.

Sarah took one phone call, and that took her right out of the magic of Personal Free Days.

When you say you’re going to have a Personal Free Day, but then you say you’re going to take just one phone call, it almost never works. It isn’t just five minutes. You’re thinking about it for a couple hours beforehand, then if the call doesn’t go the way you want it to, you’re thinking about it for the rest of the day, or longer. I’ve heard some version of this story dozens of times, and it’s always the same story with the same ending.

When you’re taking a Personal Free Day, be completely free. That’s a true Personal Free Day.

Then and now.

With the practice of taking Personal Free Days firmly in place, Sarah has evolved her life and business significantly. Today she only travels if she wants to, she has molded her work schedule to only do client work three days per week, and she has built in 12-weeks of Personal Free Days throughout the year.

And it all started with the practice of taking Personal Free Days.

My challenge for you is to start by scheduling one or two Personal Free Days into your month, no matter how busy you feel.

And if you feel there’s just no way to do this, let’s set up a quick conversation to sort it out. Remaining on the hustle hamster wheel is optional. Change has to start with taking small steps that won’t seem comfortable, or even make sense, at first.

Live bravely,

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