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As 2018 comes to a close, I’m reflecting on what’s gone well and not so well. One of the things that feels like a win, but also feels a little flat, is crossing the five year mark as an independent business owner. Is it really a win if my 5th year in biz felt a little out of sorts?

And by “a little out of sorts” I mean that I decided to shift my business model and it’s taken me approximately 10X longer to do it than I thought it would. Meanwhile, my revenue has dropped off a bit and everything has felt a bit like taking 3 steps forward and 2 steps backward.

On the other hand, I had more personal free time, my profits increased, and I generally had more fun with clients. I also got to experiment with quite a few new ideas that I’ve been sitting on for some time.

But if I’m completely honest, 2018 has been the year that’s challenged me more than any other since I’ve started this business.

I think a lot of it has to do with my expectations and comparing my business to where I think it should be or where others are at with their businesses. I know that it’s ridiculous to get caught up in the comparison game but it’s hard not to.

And working through a business re-design, along with a complete rebrand, took way more energy and time than I expected. The impact on other areas of my business has been a really tough, and resulted in much slower than expected growth.

It’s been a humble reminder that everything I’ve said “yes” to has meant saying “no” to other important goals and projects. Deep down I know that it’s been an important year of making meaningful decisions that will have a long-term effect, but the hard part is having the patience to see it through and the faith that I’ve made sound decisions.

The last time I felt this kind of discomfort was 5 years ago when I was laid off as the Western Region Sales Executive for a big tech company. I had just been congratulated on achieving my best quarter in nearly four years …and then I was simultaneously given the boot.

The job was a good one with a great salary, commissions, an expense account, and bi-weekly travel to some great cities for client visits and sales calls. But after four years of giving it my all, I was told that my contribution no longer mattered.

I had spent four years time pouring my energy into a career that came to an abrupt and unexpected hault. It felt like all those weeks spent on the road away from my family and friends, all the sacrifices I had made, were for nothing.

And that was pretty tough for me to accept at the time. But in hindsight, it was the very thing that launched me onto the journey I’m on today.

The Entrepreneur Within (a.k.a. the Wise One)

Over the past 5 years, an inner voice has started to emerge. I like to call it the ‘Entrepreneur Within.’ This dialogue with the ‘Wise One’ has grown increasingly important over the years. And if I were to recap the highlights, it might sound something like this…

Year 1 (2014)

Me: “I’m gonna go for it. How could this possibly not work out?”

The Entrepreneur Within: “Go for it! But honor both diligence and patience. Don’t lean too much on one or the other. You’ll need both for this journey.”

Year 2 (2015)

Me: “This is a little harder than I expected. I better go and invest a bunch of money on coaches and courses and workshops to ensure this whole thing works out.”

The Entrepreneur Within: “Dude! [insert the face palm emoji]”

Year 3 (2016)

Me: “There’s no way I can keep up this pace. I mean, I’m working harder than I did in my last job but at least I’ve got all these great clients.”

The Entrepreneur Within: “Congratulations genius! You just created another job for yourself …without a 6-figure salary, benefits, a 401k, or health insurance.”

Year 4 (2017)

Me: “Ahhh …finally. I’ve got a successful 1:1 coaching biz. I’m having more fun than ever but still running pretty hard. It feels like this should be a little easier though. I think I’ll change my business model.”

The Entrepreneur Within: “Whoa. Maybe you shouldn’t pivot too quickly. Listen to your customers and do fewer things, but do them well. Having a business that does a lot of things but doesn’t do anything well is useless. Your goal should be to definitively say that your business is the best at doing X for market Y. Be sure to ask yourself, “Which customers do I care most about, and what can I do to make their experience even better?””

Year 5 (2018)

Me: “Why does it feel like I’m going through hell? Have I missed something? I know that entrepreneurship requires constant evolution and reinvention but why does this feel so painful? It feels like I’m starting over, except worse, since I also feel like I should be further along by now.”

The Entrepreneur Within: “Welcome to the ‘Trough of Sorrow.’ Didn’t you know this is part of the path? The things that got you here are the exact same things that will keep you stuck here. Take stock in everything you’ve learned along the way and use it to fortify yourself. This will undoubtedly make you a better business owner and a better person.”

Marching Forward

After much reflection (and a glass of good bourbon), I’ve aligned myself with some key themes that I’ll be leaning heavily on in 2019. 

If your work matters deeply to you, the doubt and fear around it will never subside.

  • Feeling scared or doubtful? Keep showing up.
  • Worried about criticism? Keep showing up.
  • Afraid you’ll look bad? Keep showing up.
  • Feeling stuck? Keep showing up (and ask for help).

Invest in experience, shared values, and ROI.

  • I will only invest with people that are where I want to go. I’ll happily exchange value with people or companies that can help me see around corners and help me anticipate the problems that I may not realize exist.
  • I will only invest in people and companies that share similar values. There’s absolutely no reason to work with clients, vendors, partners, mentors, or contractors who don’t share similar values. Life’s just too short for anything less.
  • Unless I can determine a strong ROI, I probably won’t invest in it. I think in terms of investment and return. And yes, there’s such a thing as a spiritual, mental, and emotional ROI.

Let your work itself be the biggest reward for working.

  • You know why I coach so much? It’s because I love to coach!
  • You know why I love to coach? It’s because I coach so much!

If you’re going through a tough phase, keep going.

If you’re suffering – you will get through it. You’re in it because your soul is up to the challenge. You’re in very sacred territory and the gains will be worth it. It’s hard to see when you’re begging for mercy or ready to quit, but the struggle is getting you ready for great things. You’ll soon be ready to soar. To new heights that wouldn’t be possible if it weren’t for the perspective and wisdom gained from your struggle.

So, welcome the profound and transformational overhaul of your business and personal life. And know that you will be fortified because of it.

We’re in this together.

To a prosperous 2019 🎉


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