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Outsmart the Hustle

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As 2020 draws to a close, I’ve been doing a lot of soul searching around the forced constraints of this year and how they’ve affected me as a coach and business builder.

I love my work and I’d be lying if I told you there weren’t more than a few moments of serious concern and bouts of fear over the past 9 months.

Early this year I decided to completely unplug from my business for most of February to experience a once in a lifetime adventure in Tanzania Africa with my wife and an amazing group of people. This was the first time in 7 years that I completely unplugged from my business for that long. And just as the return flight touched down in Portland, COVID-19 was starting to become ‘a thing’ in the US.

I can remember thinking to myself; “What if my coaching business dries up and goes away?” I’m grateful that didn’t happen. But it did mean that I’d be canceling my cherished peer mastermind program that was built around meeting in-person three times in 6 months.

And it also meant that I’d be canceling a North American tour to co-host 7 ‘Coaching UNconference’ events that I had been planning for two months with another coach.

Much of 2020 felt like one big cancelfest.

And canceling meant less business and less money. And it also meant that my outlook on running a coaching business changed pretty dramatically too.

It became blatantly clear that I wouldn’t be able to do things like I had been doing them.

The constraints of the past few months have impacted me + my business in some pretty profound ways and I’m going to share how COVID-19 has changed my coaching business forever.

I’ve rediscovered what it means to ‘Outsmart the Hustle’

I love my work. I’ve been a business coach for the past 7+ years and I always tell people that I have the best job in the entire world.

But I was hustling harder than I realized and I didn’t even know it. This… coming from the “Outsmart the Hustle’ guy!

I like to tell my clients that hustle is the thing that gets you in the game, but it’s totally optional after a certain point. Most businesses like mine can hustle their way to about $200k, maybe $300k per year, but then something else is required because hustling isn’t sustainable and WILL lead to burn out.

The dirty little secret of freelance work like I do (i.e. coaching, consulting, coding, designing, speaking, etc) is that if you don’t show up to do it, no money comes in the door. In other words, if you want to grow revenue or impact, you generally have to work harder. The math is pretty simple.

As the constraints of COVID-19 settled in, I began to see how I was still hustling. Outside of my trip to Africa, I couldn’t remember the last time I hadn’t done some work over the weekend. And there had been more days than I’d like to admit where work felt more important than taking a full hour for lunch or fitting in my daily workout. And more times than not, I just felt, well… busy.

And the biggest signal of me feeling stuck in hustle mode is that I was still telling myself the seductive little lie that if I just kept working harder, then someday in the future things would get better and I’d get to work less.

And this goes against everything I stand for. In fact, the entire reason I decided to work for myself was to have more freedom and control over how I live my life every day.

I was still trying to escape the pesky belief in my head that was screaming; “More freedom and wealth comes from working harder than everyone else.”

And, yet, in my world of coaches, the people I admire most are those that work smarter vs harder. They value intelligence and smart business design vs trying to outwork everyone else.

They know that the quickest way to having the business you want is to start acting like it before it happens. In other words, they do the exact opposite of what I was doing – thinking that putting in more work will get me to a certain desired result at some point in the future.

I know a few of these smarty pants coaches and almost no one hears about them because they tend to fly under the radar. They are NOT your traditional ‘thought leaders’ and many of them aren’t even on Instagram or Facebook. They have embraced their specialized genius and they own a small slice of a market that’s tightly focused and leverages their intellectual property and their domain expertise. And they all have a really simple business model – most offering one or two core services. That’s it!

COVID-19 has been my wake up call. It has given me the space and time to reacquaint with my desires and see that there is a way to enjoy my business more while hustling less.

Decisions I’ve Made

As a result of COVID-19 forcing things from my plate this year, I can see pretty clearly how much I was still tied to the idea of hustling. So over the last couple of months I’ve began implementing the following:

1) I will only work with clients that I’m over-the-moon excited and inspired to work with. This is a combination of knowing who I want to serve, how I can help them, and a pretty damn good values alignment. To boil it down even further, I help coaches who are ready to make their first $150k and/or those looking to develop deeper market expertise + impact while advancing their specialized knowledge.\

2) I am limiting (i.e reducing) the number of 1:1 clients I will work with. I am doing this so that I can focus high quality energy into ramping up and delivering a new hybrid coaching program (Coaching That Sells). No more telling myself that I can do it all. Much of 2021 will be dedicated to simplifying and serving a very specific audience to achieve some very specific results. And I can only do this if I’m willing to let go of having a full 1:1 client roster and make room for getting an important initiative off the ground.

3) I will embrace simplicity as the path forward. I will build my business around One Core Offer (Coaching That Sells). I will only have a select number of 1:1 clients outside of my Core Offer as I shift my business towards a model that increases my impact, keeps me sane, and has me in complete alignment with my own mantra; “Outsmart the Hustle.”

4) I will slow the F down. Deep down I know that mastery can’t be rushed or forced. I will restrain myself from chasing quick money and shiny tactics and strategies. I know this will require a new level of business maturity and will mean I say “no” a lot more. It will be hard to say “no” to ‘now money’ in exchange for creating legacy work. This will enable me to make the leap from ‘freelance coach’ to ‘coach entrepreneur.’

If you want to hear a bit more about how I’m achieving this by keeping it simple, have a listen to my recent podcast interview (Bigger Isn’t Better) on The Holistic Marketing Podcast.

You’ll hear my perspective on:

  • What it means to focus on simplicity over growth.
  • The disempowering ‘lie’ that we need to offer more.
  • How to commit to slow but intentional growth.
  • Why it’s important to have clean boundaries.

I see so much out there about what we should be doing as entrepreneurs and it’s exhausting! If took 10 minutes right now and went to LinkedIn, Instagram, or Facebook, I can assure you that I’ll be served up endless gurus telling me that my business success hinges on; how to do FB lives, IG stories, FB ads, webinars, building sales funnels, writing my book, focusing on SEO, doing cold LinkedIn outreach, starting a YouTube channel, blogging, virtual workshops, writing a newsletter and on and on and on.

This is enough to make anyone crazy, overwhelmed, and full of uncertainty about what to do. And none of these things are inherently bad or wrong but trying to do too many of them, or do them in the wrong order or at the wrong time, will set you back months or years and we just can’t afford this as bootstrapped business builders.

We’ve got to be more strategic, and smarter, and instead of chasing tactics and strategies, we need to have a simple game plan for building the foundation of our business with the least resistance and the highest probability of succeeding. And this almost always involves doing less, not more, and keeping things really, really simple.

What shifts have you made (or decided to make) as a result of 2020? I’d love to hear.

Hit reply and let me know. I’m hot on this topic right now.

Live bravely,


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