Over the last year, we’ve shipped more courses, products, and programs than we had in the previous five years, and there’s been a flood of both new and old posts being published here and at Medium. I wanted to take a bit to let you know what’s going on behind the scenes, and to show you that, we need to do a bit of retrospective. It’s been awhile, so we have lots to catch up on.
I’m going to go almost all the way back to the beginning for two reasons: 1) we have a lot of new readers (we’ve almost tripled our readership since last summer) and 2) Productive Flourishing turned ten years old back in May. I didn’t expect the anniversary to be as big of a deal to me as it was, and “big deals” always lead to a lot of contemplation and reflection for me.
For context, PF started as a side project staffed by one person (me) who really had no idea what he was doing as far as running a business goes. Sure, I’d led military teams and done more than I wanted to do in academic admin, but I had no formal business training and was learning to build an online business in what was still very much the Wild West of internet entrepreneurship. It’s not just that ten years is a long time in internet years, but the technologies, strategies, and cultural norms were still emerging.
I also didn’t start the business with anything like a nest egg to draw from as I built the business. It was bootstrapped on revenue, meager discretionary income, and credit. Like many bootstrapped businesses, it was under capacity in two ways: the one person in the business didn’t really know what he was doing AND there weren’t enough hours to go around.
I wrote posts for two years or so before I was able to be in the business full time, and were it not for others nearly demanding that I work with them as a coach, there’s a good chance I would’ve just written for another few years. I want to be clear here that it was revenue from my consulting and teaching that enabled me to go full time, not my writing. But it was my writing that created the opportunities for the consulting and teaching in the beginning and continues to create those opportunities now.
‘Book or Bust’ Led to Bust
Sometime around mid-2009, it became clear that it was time for me to start writing a book on productivity to capture the body of work I was creating. I already knew that writing a book was going to be a major undertaking, so I started clearing my creative decks just to work on the book proposal and book.
And because I knew myself and my patterns, I knew I’d need to cut back on other commitments and opportunities to do it. So I stopped making other things, stopped traveling, and stopped blogging as much so that I could redirect that energy to the book.
All that sounds very good, but it turns out that what I didn’t really know about myself at the time was that I’ve got a hangup about writing a book on productivity, in the sense that all it takes is a near-related book coming out for me to feel like there’s no need to write my book.
Additionally, as I dug into the research on how to publish a book, I became aware of how many productivity books there were out there and how publishers were looking for very unique angles, large lists, and research- or story-driven content. I didn’t feel like I had any of those, and a succession of books like Making Things Happen, The One Thing, and Deep Work sent me into a creative tailspin every time they were published. It felt like every successive productivity book made my body of work less relevant and needed. (It still feels that way most days.)
Oddly, I didn’t have the same trip-ups when it came to the entrepreneurial content and frameworks I was creating, sharing, and teaching with clients and students. That seemed easy, so it occurred to me along the way that maybe I should instead focus my efforts on writing a book that helped bootstrapped entrepreneurs grow their businesses.
As I started working on that book project, I got a lot of feedback from publishers that they weren’t sure there were enough readers in the market for a book like that. This was before The Lean Startup and $100 Startup proved yet again that there was a big and broad market of people reading books on entrepreneurship. I learned a lot of other things about publishers at the time, not the least being how little some of them understand what people want to read, or how to do effective digital marketing.
I spent a few years scoping out book projects that I could sell to publishers before finally getting fed up and self-publishing The Small Business Life Cycle since that was the book right in front of me that my audience wanted, that I was getting search traffic for, and that I knew would help a lot of people. I was tired of all the book proposal writing, trips to New York, getting divergent feedback from all over the place, and talking about writing a book rather than just writing a damn book. I was also leaning into the fact that between 2008 and 2013 when I wrote The Small Business Life Cycle, the world of publishing had changed in ways that we’re still coming to grips with.
While it’s true that I had my own emotional journey with book-writing, what made it worse was that Angela and I were going through a few transitions and crises that made it hard to focus on the book.
Transitions and Crises
At the beginning of January 2010, Angela came to the realization that she was done with academia. She had been teaching sociology at the University of Nebraska, Lincoln — where we both did graduate studies — and had achieved quite a bit as a graduate student, but, nonetheless, she was miserable and it was literally making her sick. I had already determined that, at least at that time in my life, being a full-time academic wasn’t for me, and I was elbow-deep in building PF and having a blast doing it (except for the whole book thing mentioned above).
We ended up moving to Portland, Oregon, seven months later, after a brief bit of being homeless because our house in Lincoln sold faster than expected and it took longer to close on our house in Portland than it was supposed to. Good times.
Shortly after moving here, Angela went through a period of emotional trauma that led to a breakdown. After taking a few years to get her back to good emotional health, we were in a car accident that laid us up for awhile. Our lawyer advised us to not talk about the car accident and its effects on us since the insurance company would likely research our social media accounts and website to find evidence that it wasn’t the car accident that caused our injuries and pain but rather the fairly active life we lived. So, despite the fact that there was about a year where I either couldn’t work longer than a few hours at a time or was trying to figure out how to do the creative work I do while in moderate to severe pain, I couldn’t really share any of that with anyone but my clients and friends in private conversations.
While it might not be true, I feel like there was a period from 2011 until about 2015 where I disappeared or was very scarce, at least compared to how I showed up prior to mid-2010. We were on a growth plateau since there just wasn’t enough for me (or Angela) to do besides maintain the ground we’d won. It’s actually pretty phenomenal that during that time revenue and profit still grew, but in 10–15% increments rather than the faster growth experienced before then. There were some highlights during the period, sure, but most of my effort was spent serving clients, doing what speaking I could do, and continuing to maintain and build relationships as best I could.
That period of time was one of the best teachers I’ve ever had, only eclipsed by my deployment during Operation Iraqi Freedom. I had to learn to do more in the business with less energy and fewer resources. I had to learn which were the critical functions for maintenance and growth and to focus solely on them. I had to learn to let go of what was above my capabilities and to not compare what I was able to do now with what I was able to do before. And it grounded me in the reality of what it was like for so many other people, who, due to pain, caretaking obligations, chronic illnesses, or major life transitions, were just unable to do what they wanted to do. Empathy, compassion, prudence, focus, acceptance — they came at a high cost, but they’re priceless.
Stepping in to Keep Live Your Legend Alive
The worst of the physical and emotional challenges from the Car Accident / Reset period subsided by early 2015, and Angela and I were getting back to stretching our wings. Throughout that period, we had some amazing teammates come and go, but we were tired of the turnover that’s a natural part of working with people part-time. We started hiring full-time employees near-exclusively in 2014 because we wanted to invest in people and have those people invest in the business long-term; the exceptions to this were design, editing, and advertising since we didn’t have the work or the revenue to hire people to do those functions full time.
We had already grown our team to seven people when I learned that my friend and client, Scott Dinsmore, had tragically died while hiking Mt. Kilimanjaro. I had been working with Scott for about a year and a half — long enough to know his business inside and out — and his teammates knew that we were working together, so they started asking me what we were going to do. Chelsea, his warrior-widow, was out of reach in Africa, and it really wasn’t clear what was going to happen, so I stepped in to direct business activities until I had a chance to talk to her — I was more concerned that we’d run into too many people doing something because they felt like they needed to do something, but things that really didn’t help Chelsea or Live Your Legend. I was also keenly aware that I could be one of those people, so I tried to make sure we did as little as possible until we could communicate with Chelsea to see what her wishes were.
Having been trained in the Army to support families and communities who had a loved one taken away from them was incredibly useful here, as it gave me some frameworks for what to do in this situation that was unprecedented in so many ways. Scott had a huge audience and had made a personal impact on many of those people — it’s just the bright soul that he was — and many folks were grieving but didn’t quite know how to process the death of a friend they’d never met but loved dearly. My job during that period was, in order of priority, support Chelsea, stabilize the business, and support the community at large.
The trick here, though, was that it was very unclear how long I’d be working with Live Your Legend in the transition or even what we should talk about publicly. I also was very sensitive about keeping the focus on Live Your Legend and Chelsea (to the degree she wanted the focus to be on her) and just getting Live Your Legend to a place where Chelsea could run it if that’s what she wanted to do, which wasn’t clear at first.
The three quarters that followed were some of the toughest quarters of my life — it was probably harder than being deployed. To support Live Your Legend, I had to divert my attention away from PF and work another three to five hours a day. Since both teams needed additional capacity, with their founders either gone or distracted, we hired folks on both teams. I personally went from just getting used to running one business team with five people to running two teams with fifteen to eighteen people, depending on how you counted. We were all swimming in an ocean of uncertainty and figuring it out as we went along.
While I would do it all again in a heartbeat — though I’d do some things differently next time around knowing what I know now — PF suffered during those quarters and the ones that followed simply because Live Your Legend got more of my strategic and leadership energy than PF did, and I didn’t have the time, energy, and emotional bandwidth to create much to fuel PF. What you feed, grows, and PF was sharing the smaller portion of the food I was making.
The upside, though, is that I was successfully able to step away from Live Your Legend, and Chelsea and her new team have great things in store. On some key metrics, Live Your Legend was actually performing better than it was before, but, in fairness, a lot of that was because of the Live Your Legend community and the outpouring of love and support that was sent Chelsea’s way. To get in and out of a transition like this in three quarters with the business in as good a state or better is remarkable, but, again, I can’t take the credit for it: Scott left a living legend, Chelsea is a warrior, the Live Your Legend transition team was amazing, and the Live Your Legend community is bar none one of the best I’ve had the honor of serving.
Another major upshot is that TeamPF became far more resilient and capable. Angela stepped in and up to the plate and has become a powerful business manager and coach. Shannon continues to amaze us with her steadiness and adaptability and kept our client services running. Josephine (Jo) earned her wings by coming in and managing the growth projects I had on deck that really started to pay off in the first two quarters of this year — Jo essentially replaced the operational management that was a major portion of my job. Jess continues to have an astonishing ability to pick up and run all sorts of projects, while still rocking great designs and A/V editing. And I’ve gotten even better at designing and building workflows that eliminate me from the execution of those workflows.
By the time we rolled into July 2016, though, I was cooked. Twelve- to fourteen-hour days had become the norm, and the emotional and spiritual costs of the previous year were starting to come due. What I’ve learned about myself is that the cost of soldiering through something shows up a quarter or two after the mission is complete, and it was obvious that I needed to take a recovery sabbatical.
And then Philando Castille and Alton Sterling were killed by police officers. The videos of both shootings uncorked something that I had until then successfully been able to put a lid on. While every case of people being murdered by police officers is an injustice worth feeling into, it was Philando’s that undid me.
Black Lives Matter and Election 2016
To be honest, I’m still processing what it was about Philando’s shooting that undid me, and it’s probably a cluster of things. He reminds me of my brother in some ways. It happened in front of his wife and daughter. Watching a man die. Knowing in my bones that the police officer would be acquitted despite the circumstances or being in the uncomfortable place of knowing that we should be surprised and joyous IF he was found guilty. And really accepting the limits of how much our country really does not value the lives and struggle of black people.
My emotional resilience was already tapped by the Live Your Legend odyssey, and the fact that I had and have to be especially emotionally resilient just to exist as a black person in America cut me to my core. Even in the cases where we’re not in clear and present danger, we have to guard our hearts and eyes from what we see every damn day; we’re always one Facebook update or tweet away from confronting the systemic injustice that rains upon one of us for no other reason than being black. It’s an existence akin to having to constantly walk down a dark alley in the middle of the night. Even when you make it out of the alley unscathed, the haunting feeling sticks with you and might subside shortly before you have to do it again.
I had made a conscious choice to NOT talk about what it’s like to be a black professional in America for many reasons that I shared in To Be Black Is To Be Less Free. Philando’s and Alton’s killings tore down that wall, though, and I couldn’t not talk about it anymore. In short, the murders broke the compartmentalization mechanisms I had, and I couldn’t contain the dark emotions that I had so adeptly managed to put away.
At any other time, I probably would’ve had a bout of despair and anguish that would’ve passed, but we were also at the tail end of the election that yielded Donald Trump as our president. Whatever wall I had started rebuilding came crashing down on November 8th. While we can’t point to any one reason for why Trump won, racism, sexism, xenophobia, and homophobia were strong factors in the mix. Any win fueled by such things would only be followed by policies and governmental action that reinforced them under the guise of “a mandate of the people.”
July 2016 through February 2017 was thus emotionally intense for different reasons than the quarters that preceded it. For me, it was coming to grips with how I was going to respond to this old-new America that I’d fought to protect but now had trouble identifying with.
What became crystal clear, though, is that my best move is to focus on the long game rather than getting involved in the daily hysteria that’s at best cathartic but rarely changes anything. My dad being diagnosed with dementia in February 2017 was also catalytic on this journey, as I realized I had some building to do so that I could be more present and helpful with that transition. (That’s still ongoing.)
Full Speed Ahead
So, yeah, there’s been a lot going on behind the scenes for a while. Most days, I sit with the dual truths that I’m frustrated with all of the lost time and I’m grateful for what I’ve learned during that “lost” time. Had all of it not happened, I’d likely have another book or two under my belt and be financially better off. Had all of it not happened, I may not have progressed on the spiritual and emotional levels as far as I have. Regardless of whether I wanted the gifts of wisdom, they’ve already been paid for, so I might as well accept them.
Throughout all of the trials from the past few years, we kept building, even when it felt like we were moving so slow and it wasn’t moving us forward. But it was.
Due to a lot of that building, we’ve doubled the size of our audience since last June. We just crossed 25,000 subscribers, and if we keep doing what we’re doing, hitting 35,000 subscribers by the end of the year is not out of our reach. Since launching the podcast, we’ve shipped at least one episode every week. We continue to work with great clients at ever higher levels of accomplishment. We’ve done the Monthly Momentum Call every month since it started in 2012.
We’ve also invested a lot in the capabilities of our current team. A key metric I’ve been tracking is how capable the team is running and growing the business without me; while I always build teams so that their survival is not dependent on one person — a lesson learned in the Army — my experience with Live Your Legend only amplified my focus to do so. We did a quick assessment after the launch of Epic Launch Playbook, and the team’s readiness to execute a launch was in the 85% range, up from about 45% last year. Furthermore, we have most of the capabilities we need in-house now to do great product development — we’re not at the whims and timetables of freelancers, which makes a huge difference.
While our capacity was limited, two things were de-prioritized: blogging and product development. But I’ve still been advising, speaking, and teaching over those rebuilding years, and those are the catalysts for what I create. I’ve thus been sitting on strategies, frameworks, insights, routines, and all sorts of other stuff that has been really helpful for those who’ve seen them. As I’m writing this, we have five products in the queue, and I’ve mapped out the arc of three different full-length books.
I’m also re-energized to start blogging again for reasons I’ll share in another post so that we can finally put a bookend on this one. I’ve been frustrated, embarrassed, and conflicted about how “little” I’ve been blogging over the years, as you can tell from stints like the No Hiding project. As I’m writing this post, there are eight other posts being edited and prepped for publishing. Before I started my current productivity/schedule experiment, I was writing content to publish every day, but I realized that writing was getting a free ride as far as being counted in the amount of hours I worked per day, and that was causing my days to be unsustainably long. I also diverted some of those focus blocks back to the book, and (surprise, surprise) I’m getting some momentum on it.
What’s true for me is that the more I create, the more I create. I develop habits, workflows, and supportive feedback loops that make it easier for me to keep doing it and doing it better. So the more I write, the more I’m going to write; the more we focus on getting our trapped content packaged in courses and products, the more we’re going to be able to get our trapped content packaged in courses and products. (This is one of the reasons the team went from 45% to 85% in launch readiness — we’ve been doing it enough with the same team for us to do the cross-training, process building, and practice it takes to get good at doing it.)
For different reasons, we’ve been steering this ship with an engine or two down — and we started with too few engines in the first place. For the first time in a long time, all of our engines are online, we know where we’re going, we’ve got the right people in the right places on the ship, and we have lots of valuable cargo to unload. We’re going to be going full speed ahead.
Full speed ahead, though, means something different than it used to because it balances getting things to you sooner with doing it in a way that doesn’t lead to continual Dunkirk spirit for us. We currently don’t have a timeline for what we’re going to be releasing since we really don’t know how long it’s going to take us to get it all produced and ready for you to see. We’re still figuring out what full speed ahead in this new way looks and feels like for us.
Bear with us as we get it all figured out. Also, thanks for sticking with us through all the ups and downs, even when you didn’t know they were happening. It’s great to be back, and we’ve got a lot of work we get to do.
Ali Luke says
I’m excited to see what’s coming. 🙂
Thank you for being so open in this post. While my business is a much smaller one than yours, and my challenges have been positive (two small children) — I can certainly understand the feeling of going off the radar for a few years — I feel like I’ve not been fully “online” since mid 2012. I’m still working on trying to be more patient and accepting graciously that I can’t produce as much, or move as fast, as I could pre-kids.
Congratulations on the 25,000 subscribers. That’s fantastic! It’s been a great privilege to watch PF grow over the years (I’ve been reading since 2008…)
Looking forward to whatever you’re cooking up next. 🙂
Charlie Gilkey says
Thanks so much, Ali! I was telling Angela the other day about how awesome you are and have been all these years. I’m excited about what’s ahead and it’s been a real treat to see you more. 🙂
WOW ! Congrats, Charlie. Your strength and resolve during all of the turmoil is SO INSPIRING ! Most of us could not have come through it as well as you have.
Just another testiment to how AMAZING Y-O-U are.
Peace, Love and Blessings to you all
Charlie Gilkey says
Thanks, Frances! While it’s not always true that what doesn’t kill you makes you stronger, in our case, it’s been true. 🙂
Dr. David Powers says
Man, I had no idea about a lot of this. We met way back at WDS II in Portland in the Do Epic Shit days. Everything since then has just been me following you online.
I’m glad to see things are awesome and picking up, and I’m really loving the content you’re putting out, especially the recent podcast with my best friend in the world Ryan McRae.
Charlie Gilkey says
Thanks, David! I’m glad to see that things are grooving better, too. Also, Ryan is the bomb.