6 Things I’ve Learned from a Year of Self-Employment

Pausing to Look Back for Clues about How to Move Forward

About a year ago I packed up my office at Baker Books and “went out on my own,” as they say.

I’m pleased to say I’m still self-employed, although that’s a bit of a misnomer for reasons I’ll get to shortly.

This is a significant milestone and bears reflection on what I’ve learned along the way. Here are six lessons that seem worth highlighting.

1. The risk was worth it.

My wife and I went into this transition with some trepidation. It’s true I had started a business on the side and had built up a financial buffer before casting off the lines of my day job.

I’ve always liked the idea of building a bridge to a new endeavor like this as opposed to taking a leap. We did our best to build that bridge before I left Baker, but it was still risky. We knew I could fall flat on my face. And we knew, if that were to happen, finding a new job could be difficult and might require uprooting our lives to a new location.

So I had a small business started, some ideas for how to grow it, and a deep desire to give it a try.

It turns out, the risk was worth it. I’m not living on Easy Street. I don’t have a million dollars in the bank. But I have managed, with help, to grow the business enough to assure both my wife and me that this really is a viable business. I am offering services others find valuable. And I’m watching books come to life, which is what it’s all about for me.

I just completed my third quasi-annual life-planning retreat. This is when I go to the woods and live in a hut for a few days without electricity or running water. It’s a wonderful way to clear out the distractions and get focused on the life I’m meant to live.

At some point, as I was either pumping water or tending the fire, I stopped and looked up. “Thank you,” I said. “This is fun. It’s fun to live out my calling, to follow my passions, and to help others follow theirs.”

I really don’t know what the future holds. Still, I have more confidence than ever that what has begun will continue. And I know, more than ever, that the risk was worth it.

2. I could not have done it without the support of family and friends.

I said above the term “self-employment” is a misnomer. The reason is because this work is far from work I do by myself. In fact, if I had to do it by myself, I think I’d fail within a week.

It’s only because of the support of my wife, my kids, and my friends that I’ve had some success up to this point. I’d be remiss not to mention the names of some of the people who have been instrumental in guiding and supporting me—people like Michael Hyatt, Jonathan Milligan, Jeff Goins, Bryan Harris, Grant Baldwin, Joseph Michael, Carissa Magras, Matt McWilliams, Jodie Von Kamecke, and Andy Traub. I’ve also benefited enormously from the Fast Track Lab Insider community that Jonathan Milligan facilitates.

And this is to say nothing of my personal friends and clients who make me way better than I could ever be by myself.

People call this “self-employment” or “solopreneurship,” but make no mistake. People who think they can do it on their own are fooling themselves. I’m just extremely fortunate to have people around me who care about me and want to see me succeed.

3. It’s one big experiment.

The big difference between working for somebody else and working for yourself is, when you work for somebody else, in most cases you have a program, a plan that’s laid out for you. Your job is to follow that plan and make something happen.

When you work for yourself, the reality is the plan doesn’t exist until you create it. Creating the plan and then executing it is one big experiment.

Entrepreneur Magazine asked Sara Blakely, founder of Spanx, to share what she’s learned as she’s grown the company to 200 employees. “Looking back at the past 10 years,” she said, “my biggest takeaway is to fire faster.” To just try stuff. That’s been useful advice to me.

I can either kvetch and worry and theorize whether something is going to work or actually try it and see, once and for all. In other words, I’m learning to iterate as quickly as possible, to fail fast, to learn quickly what works and what doesn’t work.

Here’s something I’ve noticed. Very rarely do I try something that is immediately successful. So far, my path has been, I try something, it doesn’t work, I tweak it, and then it does work, at least well enough to try again. So the only way I’m going to to make something that works is by trying the thing that does not work.

On my recent life-planning retreat, I started a number of campfires. When I started a fire, very rarely did the fire catch where I thought it would or where I intended. But if I hadn’t lit the match and put it somewhere, the place that did catch wouldn’t have. That’s how it’s been with my business.

4. Self-employment has a LOT to do with self-care.

Dan Allender, in his book Leading with a Limp, makes the profound point that we lead from who we are. Our leadership, everything about it from the tactics we use to the communication style we employ to the tone we express ourselves in—all of it comes down to who we are.

The better we live, the better we lead.

I’ve had to learn (I’m still learning) what self-care looks like, what the rhythms are, how much is too much, how much is not enough. How to care for myself when I make a mistake.

As I learn to take care of myself mentally, physically, spiritually, I become a better leader for my clients and customers. It’s tempting to drive a wedge between who we are and how we serve, but my journey, so far, has taught me that the two are inexorably connected.

It’s scary to realize that, if I fail to live into the person I’m meant to be, I end up failing those around me. But that seems to be the truth. The flip side, of course, is that as I do care for myself, as I manage my health in various ways, the better I am able to help writers get their books into the world. It’s a striking corollary.

5. A handful of systems have been the lifeblood of my business.

I want to mention just a handful of systems that have been essential to my success up to this point.

The first is a goal-setting system. Every year, and once a quarter, I think about the goals I want to pursue. I have to tip my hat to Michael Hyatt here. His course, 5 Days to Your Best Year Ever, as well as the related book we worked on, have been absolutely instrumental to me. His Full Focus Planner has also been extremely useful in helping me implement my goals into daily life. This system has given me a north star by which to navigate day-by-day.

Another system that has been invaluable is from Michael Michalowicz’s book Profit First. (Hat tip to Jodie Von Kamecke for sending me this book early in my transition.) It’s a way of accounting that jibes with how most of us naturally operate and has given me a daily picture of my finances that has been indispensable.

A third system that’s been really useful to me is actually more of a ritual, namely, my morning ritual. Every morning, well, every weekday morning anyway, my practice is to spend fifteen to thirty minutes meditating using the Calm app, reading, and filling out my Full Focus Planner. This ritual has centered me each day and kept me from getting overwhelmed with all I have to do.

Two systems have helped me with my physical health. The first is Rich Roll’s Plant Power Meal Planner. I estimate my diet is about 80 percent plant based because of this app, and I love it. The other is the tried-and-true WeightWatchers system. On Tuesday afternoons I make the 5-minute trek to weigh in and go to a meeting (workshop). I’m down over twenty pounds since starting four months ago. Also, I’ve found my exercise routine leaves a lot to be desired unless I’m training for an event. I trained for and ran a 5K with my 12-year-old son earlier this year, but what’s next? Still figuring that out.

One last system I’ll mention that I don’t use as often as I’d like but has been vital is the Day Review system. I use Michael Hyatt’s Full Focus Journal (note: journal, not planner) for this but, basically, it’s six or so questions you ask yourself at the end of the day, questions like, “What happened today? What did you learn? How can you make progress on your goals?” You write your responses to them, and it’s just very clarifying. It helps you learn what there is to learn from a day’s work. It’s been a healthy way for me to end most of my work days and has definitely helped me achieve more than I would have otherwise.

6. My success depends on the success of those I serve.

This is where the rubber meets the road. At the end of the day, self-employment is not about me. It’s about my ability, my energy, and my expertise poured out in service to the writers who are part of this tribe I’m doing my best to lead.

If you’re in this tribe, and you succeed, I succeed. If you don’t, I don’t. It’s really that simple. And that’s why it’s crucial for me to be thinking continually about you and doing my best to serve you in the best way I know how.

I’m honored to help you and hope to continue doing so for a long time to come. Thank you for giving me this opportunity. I really appreciate your trust in me.

Question: What in this article has been most helpful to you? You can leave a comment by clicking here.

Please note: I reserve the right to delete comments that are offensive or off-topic.

16 thoughts on “6 Things I’ve Learned from a Year of Self-Employment

  1. Chad, your tips are timeless and so valuable. I am starting my next chapter as a retiree. My latest venture of becoming an independent consultant is indeed one big experiment. Thank you.

  2. Thank you for sharing your wisdom once again! You’re a wonderful, humble mentor and leader with a heart to see others succeed. It all begins by taking that first step out of security and into the life you were meant to live 😉 You inspire people to inspire people and you do a darn good job of it. God bless you and your family!

  3. Most helpful in this article is your tip on reflecting on the day’s learning at the end of each day. That’s the second time today I’ve heard about reflecting on learning – guess what I’ll be doing Monday?

  4. Well done, Chad! I’ve watched your growth and service scale. Congratulations! I too am a fan of Jonathan. I’m attending his LIVE mastermind this year. You and Jonathan are my primary “go to” online professionals. I appreciate this transparent blog post. Your content was helpful and encouraging. Hopefully, I can have a success story by next year. I love the value of your membership site, too. Blessings!

  5. Ah, yes, the entrepreneurial life is truly wonderful—quirks and all. It’s been great to follow you in Bookcamp as well!

  6. Really cool to see behind the scenes for you. My family has been in a transition period for a little over a year and the last 6 months of it have been a lot like self-employment. I like the ideas of checking your goals/plan regularly and checking how things went at the end of each day. I think this idea along with the tools you mentioned will be a big help to us!

  7. I have just joined BookCamp. Thank you so much for sharing your thoughts and experience, Chad. I resonate with what you share, and I hope this new adventure will not only put me on the right path but will be of some benefit to other fellow travelers as well.

  8. Absolute gold, Chad. So many nuggets of wisdom, and a huge encouragement for those of us who are a few steps behind you. The campfire metaphor of slow starts, failing fast, and being patient was a much needed reminder.

    It’s been fun watching you make this transition, and I wish you even further success in your second year!

  9. I love your honesty, Chad. I am in the Gran Finale stage of life… very different stage of life from you, but I needed these reminders that good self care must include a certain amount of goal setting/planning. I can get bogged down in the daily routine and forget to dream or plan or set goals for growth, learning new things or new adventures…all necessary for vibrant living no matter how old we are. Your 6 things have pulled me back on track …thank you!
    Here’s to another fruitful year ahead…best wishes!

  10. This is a great update, Chad. I love reading behind-the-scenes takes, because there’s a lot to glean from other people’s journeys. I haven’t read Leading With a Limp yet, but it’s been on my TBR list for a while. I love Dan Allender! “The better we live, the better we lead.” Definitely! Thanks for sharing.

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