7 min read

This was a wild year for me. I began the year employed at CrossChx, where I was learning a ton about leadership, product management, and the healthcare industry. At one point I was managing eight members of a sales team while working directly with 7-12 engineers at any given time.

I knew that 2017 was the year I wanted to get back out on my own. I’ve shared my New Year’s Resolutions several times, but it was largely based around taking more risks and creating more “stuff.”

In February, I began working with a personal coach who helped me get out of my own way, identify my blind spots, and get over my belief that I wasn’t an “idea guy.” To this day, working with Chris has been the single best investment I’ve ever made.

Through working with Chris (and, strangely, an ad featuring Steve Martin) I made the commitment to making writing a daily practice, and this newsletter was born on March 5.

Writing this newsletter has been the biggest contributing factor to my success in 2017. Besides my December break, I never missed a day. Consistency is key for building trust, and writing forces me to actually articulate (and therefore codify) the things I am learning.

I left CrossChx in April to go out on my own, not totally knowing what that would mean. The first thing I did was some budgeting, which I determined gave me until July to start bringing in revenue or I’d have to reassess this “unemployed” thing.

Thanks to some generous friends who supported me, I was able to bring in some freelance revenue through one-off marketing projects as early as May to give me some confidence.

In May, I started my first beta group for Unreal Collective. I hand-picked five individuals I knew were actively working on their on projects, and I could see how they’d have some shared learning.

I asked them to make a weekly video call that I’d facilitate a priority, promising to help accelerate their projects in return for giving me feedback on the process so I could make some final tweaks before launching the first membership opportunity. The results were great, and I found a few weak spots in the program that I tightened up for the next group.

In July, I invested in Seth Godin’s altMBA to level up my leadership and, frankly, deconstruct his process. It was super intense, brought my personal investment on the year to over $8K, and introduced me to so many incredible people.

Again and again, I find that investing in coaches/mentors and communities of people (given proper research into those communities ahead of time) more than pays for itself.

Also in July, I began marketing the first paid session of Unreal Collective’s 12 week program. It was terrifying, I was rejected dozens of times, at more than one point I laid in the fetal position for several hours (seriously) and questioned what the hell I was doing.

But I had a goal. I was going to find 15 people who understood the value of what I was promising, and I did. It wasn’t easy! It took a lot of putting myself out there, a lot of conversations, and probably thousands of touch points to find the right 15 people.

And that was enough, it gave me validation and it further strengthened the process. We had some incredible outcomes and I’m excited to double our community next week!

I spent August in Los Angeles — I promised myself I’d create a business that allowed for living/working remotely, and this was the first swing. I loved it.

I very quietly created an 8-week coaching program that I worked through with a handful of individuals. This program is an accumulation of the biggest ideas/processes I learned in 2016/17, and the feedback has been great. I’ll continue to improve that in 2018.

Due to poor planning on my part, and despite knowing it was coming, I hit a cash flow snag in October. I realized that it would not be practical to start a new session of Unreal to run through Thanksgiving or Christmas, which meant that my earning opportunity with Unreal went to $0 for two months.

After some panicking, I simply adopted that problem into my answer to the question, “How are things going?” when I talked with people.

“Things are great! We just wrapped up the first paid group of Unreal, we had some huge wins, and I’m excited to totally rebuild our digital assets around their stories. But, since I won’t be starting another group until January, I’ve got kind of a cash flow issue for the next three months.”

In very short order, I found some projects to cover my gap around marketing and WordPress development. The bills need to get paid! However, I did not plan as well as I should have for taxes, and I’m paying for that mistake now.

In December, I began marketing the next opportunity to join the Unreal Collective 12-week program. It was an interesting time to do a marketing/sales campaign, and I’m still pretty ambivalent about that timing. Regardless, it seems to have worked just fine.

2018 preview

There’s an idea in the lifestyle entrepreneur world called the “1000 day rule.” It says you need about 1000 days, three years, to recoup your corporate salary through your own business.

My goal in 2018 is to break that rule, and do so by making the leap from freelancer to entrepreneur.

The distinction isn’t a big one, but it’s a Seth Godin idea that if your business is only making money when you’re working, you are really freelancing. Once your business is generating revenue without you actively working all the time, you’ve built a business bigger than yourself.

I’m a little hung up on this. For the last year, I’ve been dead set on building a company of one — I didn’t want to have employees. I didn’t want to create a business that ran me and I didn’t want to lose any of the flexibility and freedom I was working so hard to create.

I’m starting to come around to the idea of building a team, or at least a support staff. There is only so much one individual can do in a day, and the real value comes from spending time creating assets to be leveraged again and again.

If I remain focused on staying a one-man operation into perpetuity, I’m severely limiting the amount of time I can create assets, which slows down the timeline of having those assets done and able to be leveraged.

In short, I need to expand my offerings and actually productize some of those offerings. And that’s what 2018 is going to be about.

Some misc. goals for 2018:

  • Balance consumption with creation
  • Create specific eating/sleeping/exercise routines
  • Be more polarizing in what I share here and on social media
  • Further define my niche(s) and value proposition(s)
  • Be more professionally ‘weird’ (as opposed to just personally weird)
  • Continue to invest in myself and my network
  • Be more protective of my time
  • Create a financial forecast/projections including cash flow for 2018 and withhold properly for taxes

I’ve already made my first two investments of 2018, including a highly technical time management/planning program and re-enrollment in Seth Godin’s marketing seminar.

The first six months of my year are planned out with goals and objectives, and they are pretty ambitious. As my friend Michael told me a few weeks ago, “You know you could run faster if you wanted to.”

And it’s true. Frankly, if I would’ve ran faster in 2017 I could’ve run two full sessions of Unreal Collective and avoided my cash flow problem.

The single most important habit I got into in 2017 was creating detailed plans and timelines for my tasks. It sounds simple, but it really takes a lot of repetition to find muscle memory and embrace systems as part of your life.

One more plug: the Unreal Collective 12-week program gives you that system out of the box. By starting your 2018 with 12 weeks of guided help creating plans and systems, you’ll develop the muscle memory to carry through the rest of the year. I work myself through the same process as you, in real time. (Apply here)

An immediate new plan is batching more of my tasks. Every Sunday I will be writing and scheduling my week’s worth of emails so that I maintain my creative energy during the week for the tasks of the day.

Thanks for being along for the ride, and I look forward to learning more about you in 2018!

PS: If you enjoy this newsletter, please share it with a friend or two. Tag me on Twitter (@jayclouse) and share this link. I’d love help spreading the word, and I’d love to hear your feedback about what you like about reading this. Thanks!