Justin Ricklefs


Farewell, 2022. A Look Back, to Move Forward.

Last New Year’s Eve, I was in the unfinished area of our basement. In our makeshift home gym that has a hodge podge of workout equipment. A small black and white banner hangs, slightly off balance, over the mirror we’ve never hung, that says “Tough as a Mother”.

It was a Mother’s Day gift a few years ago for Brooke. And if you know her, you know it’s true.

Snow was on the ground. 

I was smack dab in the middle of the toughest stretch of our company’s then four and a half year journey, but I didn’t quite know it yet.

I play hopscotch a lot with my Apple Music habits. 

Going from country, to classical, to 90’s grunge, to 90’s rap, to The Avett Brothers, to Taylor Swift, to Enya. 

That current day, I hit the “Enimem and Similar Artists” button on the jukebox. 

I was struggling to do a few push ups, when Macklemore’s “Next Year” song came on. I’m a sucker for a good Macklemore track, and this one had me from the hook. 

“Next year’s gonna be better than this year…” 

Man, I sure hoped so.

I was feeling this weird mix of gratitude for a good (overall) 2021, but also this longing for something better in 2022. 

Won’t that always be the case every NYE? 

Our human condition, in its beauty, hope, and brokenness, longing for some future event to make us feel better. 

As I sit here a year later, my soul still longs for Macklemore’s refrain to ring true. That next year will be better than this year. Always and forever. 

This year was great, overall, but it was full of surprises, challenges, and learning. 

But, slowly and stubbornly, I’m seeing that the real gift isn’t in a future state or date, but in the power of the present moment. 

As an Enneagram Seven, I’m both blessed and cursed with the ability to get hyped, amped up, and bring others along with me to the magic carpet ride of what’s to come. And yet, in my middle age, my life stage with our family, and the growing awareness of my own soul, it really is the stillness and serenity of each passing second where life’s greatest adventures lie. 

So, it’s in that spirit, I share a reflection of my 2022. 

Mainly as a way to write my way into some themes and learnings, and also as a way to share some of my journey in case a piece of it resonates with your own. 

I’ll loosely organize this by topic / theme / role, with one big caveat. 

There are no compartments. 

There’s only whole humanity that plays out in a variety of contexts, emotions, and experiences.

As a recovering compartmentalizer, it’s important for me to state this. 

That said, get a cup of coffee or a glass of champagne, and let’s roll. 


20-year-old me wouldn’t have believed it was possible, and 42-year-old me acknowledges it’s the most refining, exhilarating, terrifying, thrilling, humbling professional road I’ve walked. Owning and operating Guild Content, being a partner in SquareWork, and being the General Partner of Squids Pro Wash each deserve a few thousand words of reflection, but I’ll summarize the biggest pieces. 

  • Bootstrapping is Courageous and Crazy. On one hand, I’m so proud that we’re 5.5 years into a cash-flowed (and goodness, it’s ebbed and flowed) marketing agency that employs 11 incredible humans. As a new client told us recently when asking about our financial structure, and me telling him the journey, he said, “Good, that means you’ve been refined by the fire.” Damn, was he right. And yet, on the other, in this era of stronger capital sources, wise and gracious investors, and other models of financing, our lack of outside capital has hamstrung us in ways too. Most significantly, the margin of safety that comes with lots of liquid cash in the bank. 
  • Not all Partnerships are Sinking Ships. Horror stories abound of partnerships gone poorly. I know a few close friends and colleagues who have experienced them. Guild was a partnership in the beginning, and I can own I wasn’t the healthiest and best person of myself many times as we navigated the early waters. Now, for the next five years of Guild, we’re considering other partnership arrangements, and Brooke and I are much more open-handed about this than we’ve been in the past. Mainly because we’ve seen how abundant and generous structures have worked. Specifically, our partnership in SquareWork with a dear and trusted friend and the acquisition and formation of the Squids Pro Wash ownership structure where ten friends, colleagues, and partners (including the new day to day operating partner) serve as Limited Partners in the entity, all with a shared and common goal of further growing the incredible brand Brodie Leap built. All of these scenarios have required creativity, honesty, some tough conversations, vulnerability, and most of all, trust in each other that a bigger story is being written than anyone individually could write.
  • Entrepreneurship is Soul Work. Owning a thing is great, but goodness, don’t underestimate the toll it can take if you let it consume you. And, at various points and to varying degrees, it’s consumed me. In ways like: working every night, working on weekends, working on vacation, being lost in thought, not being present with my family, not being able to fall asleep because my anxiety raged, treating team members poorly, harboring resentment, feeling deep shame and insecurity, the list goes on. And yet, it’s been such a beautiful gift to learn that even though I “own” a thing, I’m actually not in control. I don’t have the power to make the world spin. There’s a big God with a big heart for us, and it’s my journey from fear and scarcity to sufficiency and surrender that has been an excavation and gift of the soul, disguised as owning a business. 


Watching leaders emerge and develop is a surprising joy for me. Most specifically for me this year are two people. First, it’s been a privilege seeing Racheal Burnett step into her COO role at Guild and all the magnificent and important work she’s led in just a few short months since July. And second, Ryan Campbell grabbing the day to day reins at Squids has been a godsend and brought such friendship and life to me. I’ll never forget, over dinner with our wives as we were kicking around this crazy idea of him joining the Squids Squad, he looked me in the eye and said, “let’s build a business.” Both of these leaders operate out of deep faith, integrity, and fill gaps I didn’t even know existed. A few other key learnings:

  • Direct, Clear, Kind. In various leadership roles in my career, I’ve primarily been the kind, encouraging, empowering leader. Which I think generally resonates well with people. I don’t scream, yell at, or criticize. At least not very often. However, that type of structure only allows a select few to really thrive. For the rest of humanity, they struggle because they don’t know my exact expectations (oftentimes because I don’t know them myself) or exactly when they’ve missed the mark (and of course they know I have high standards even if I don’t tell them). I’m a massive work in progress here, but instead of couching coaching in kindness and bush-beating, I’m working hard on speaking right to the thing I see that missed the mark or the specific vision I have for a project or whatever. A former coach of mine said, “The frustrating thing about you is that you act like you don’t have a process, but you have a very clear process in your brain that you don’t write down or share with others to emulate. And then you get mad at them for not reading your mind.” Ouch. But he was 100% right. It’s hard work for me, but taking the time to write out specific expectations and processes in kind ways has been freeing for me, and provided soooo much more clarity (and therefore, work satisfaction) for those around me.
  • The Ego is a Pesky Fella. At its best, leadership is a gift best given away for the benefit of others. Being a conduit to someone else’s growth. Being in service to a greater mission. Yet, the whispers of applause, appreciation, and acknowledgement (AKA the ego begging for some attaboys) get wrapped up in the recipe. I think the work is seeing when he comes out for some reassurance, remind him he’s been a good survival partner, but is no longer needed in the truer and better stakes.
  • The Right Amount of Responsibility. At our worst, leaders either blame their team, their clients, the economy, or some other outside force that is “against them” OR play the unhealthy long ranger hero who overcompensates by cleaning up the messes, taking too many arrows, saying sorry a million times, and being soft and squishy towards others who need some of their own responsibility medicine. I’ve drifted into the second set of waters more than the first, but the wake starts really rolling in good ways when I take a healthy, appropriate measure of responsibility while holding the tension of allowing / expecting others to do the same. 


Financially, Q1 of 2022 was a major bitch. Macklemore lied to me. But it turns out, the pain and discomfort was a tremendous teacher. We were in a world of hurt to start 2022, specifically at Guild and at home. Our 2021 revenue jumped pretty good, so I made the not-so-calculated bet in the middle of 2021 to go even more on the offensive and hire pretty aggressively. Without strong financial constraints and without the backstop of deep capital (see the bootstrap point above), Q3-Q4 of 2021 saw a huge uptick in expenses while we also got hit in an unexpected downturn in revenue. I was convinced I could outrun it, outsell it, and drive enough revenue to out-earn it, and boy was I wrong. The bill came due early in 2022, and it was scary. We used just about every creative (but legal, ha) maneuver in the book, and I’m grateful as heaven we’re in a much healthier place personally and professionally in this moment, but it taught me some key lessons. 

  • Constraints are Kind. I buck against authority, budgets, and frankly, some practical best practices. The “chart your own path” instinct is wonderful for starting something, but it’s no way to live once it’s underway. Handing over the responsibilities of the Guild operating budget to Racheal and Dorothy (our Accounting and HR Manager) and deferring to the constraints and wisdom they’ve built into our operation has freed me up and reduced so much unnecessary friction and anxiety. 
  • Operate in Your Genius. Will share more below in Resources, but go read and listen to everything you can get your hands on regarding Pat Lincioni’s Working Genius model. It was a breakthrough for me this year. And personally, it allowed Brooke and me to change some long-standing roles and responsibilities we had with our personal finances. I’m an Invention and Galvanizing genius, she a Discernment and Tenacity genius. I’m good with ideas and people, her superpower is intuition and follow through. Taking this test, and then talking to our financial guy AJ Wagner (he’s the best), we felt the freedom to acknowledge, without shame, that our old system wasn’t working. The old way being me owning our budget, managing our day to day spending, and keeping tabs on our financial health. So I did what I do. Built a beautiful spreadsheet, got jazzed about the idea, put dates on the calendar, then shit the bed with all of the rest of it. Understandably, then Brooke got upset when we didn’t meet, and frustrated when I let the credit card wander into the black hole. All that to say, midyear we felt the freedom to say, wait, what the fuck, why are we doing it this way. She loves the damn details and almost always has the right idea of what we should spend money on or not. I love the making money part and coming up with the ideas of how to grow. With AJ’s blessing, we clarified the new system, and our geniuses are free to roam now. 
  • Stuff Doesn’t Satisfy. I went into the Nike outlet store in Orlando, FL yesterday, December 30th. I LOVE that store, almost as much as Costco. But I was struck with how many people were in there 5 days after surely getting some Nike stuff for Christmas. The line was 20 deep and you would have thought it was Black Friday. As my good friend Gary said once (he’s the king of one-liners, hopefully he’ll write a book one day), “Never underestimate the power of human consumption.” I walked out without spending a penny. And it felt like a victory. I’m a long way from a minimalist, but I’ve been on a gradual reduction of the material stuff clogging up my closet, and there’s real freedom in it. 


“How many people deal with, work on, and talk about this kind of stuff,” Brooke asked Rick, our counselor, a few years ago. When you’re in that seat (or couch to be specific), it’s so easy to feel bad and think of what a screwed up relationship you have. I’ll never forget his response, “The real question is how many don’t. Y’all are on the path to profound love, something only 1 out of every 100 couples are willing to walk.” This is NOT a “look at us, we have profound love” plea. In fact, if you know our story personally, you know it’s been a rocky ass road the past few years. But it’s been one that’s marked with choice, intention, and connection. And I’m blown away that I get to wake up next to her each day, she’s my greatest and deepest adventure. Here are a few truths I’m certain of:

  • Radical Honesty is the Way. I subconsciously (and consciously at times) built an image, projection, and persona of myself, our marriage, and our family in my late 20’s and early 30’s. The social media drip were hits that filled some pieces of me, so I kept it fueled. A little false humility, sprinkled in with some un-dealt with trauma, and a dash of dopamine created a playground for me to pretend and posture. It wasn’t all bad of course, but when the deeper and truer parts of me were revealed, they were accompanied by some dark shadows. “Tell the truth, no matter the consequences,” I was told early on in my soul recovery journey. Like Gollum in Lord of the Rings, I clung tightly to this precious identity I had built. She can’t handle the true truth. What a lie. And who am I to think I could make that decision for her. She’s brave, strong, beautiful, and fierce. She’s more than capable of handling my truth, and it’s the very thing she craved actually, and for years, I withheld it. I’m proud that 2022 marked another year of truth-telling for me, and for us. 
  • Codependency is Crippling. This year, in the therapy seat as I was sharing a work situation, Theresa lovingly told me, “It seems that you have some more work to do on your codependence…” The ego bowed up and wanted to say, “the fuck I do.” But my spirit rose eventually, and embraced it as more work, and learning. The crippling crutch of codependence has played out in every context of my life, but doing the work to get clear on who I am, what I’m OK (and not OK) with, and how to offer myself FROM a place of security and strength, and not FOR approval or OK-ness, is a road worth walking. 
  • Trust Love and Don’t Lose Heart. When I was at my darkest and lowest, I questioned the 1 out of 100 road. In my anger (disguising my deep fear of abandonment), I protested Rick’s counsel. His response, “Trust love and don’t lose heart.” The love of God, the love of each other, the love (and acceptance) of myself. And don’t lose heart. That anthem filled me, buoyed me, and carried me in 2022 and will as we keep going.


I wrote a post in 2014 that went viral. 15 things all dads of daughters should know. While I’m proud I wrote it, and I’m grateful for the experience, another part of me makes the squinchy-emoji face when I think about composing that when I was 34, and our oldest daughter at the time was 10. I had lots to learn in the unfolding teenage years. But goodness, those years get dramatized and projected as unbearable. In our case, that hasn’t been the case. Sure, there have been some treacherous terrain and some incredibly difficult stretches, but to witness these three young women (our son is 12 and our youngest daughter is 11) enter and progress through their teenage years has been rewarding. Here’s why:

  • Accepted their Reality. When in doubt, err on the side of pursuing relationship, honesty, and trust. Sitting with them in their honesty about their pain, confusion, depression, comparison, jealousy, anger, and hopes, without judgment, seems to be the work we’re doing most of these days. What this collective of teenagers is up against is unfathomable. And yet, they’re such an in touch, aware, brave bunch. Fighting against the realities they’re facing only causes suffering for the parents, and wishing for the good ole’ days of the Brady Bunch and house phones is denial masqueraded as whimsy. Embrace their reality, or they’ll go to great lengths of hiding it from you.
  • First to Fly. Wow. We sent our oldest to college, and in doing so, a chunk of our hearts were left in the Phoenix desert. 
  • Love > Commands. 8-year-ago dad me was pretty intent on producing good kids through good behavior. I wouldn’t have said that out loud, or maybe even been aware of it, but if they followed the rules, “obeyed”, and didn’t cause much disruption, life was pretty good. With young adults as kids now, it’s amazing to send texts like this to Brooke, “We have teenagers who want to be around us most days. What a weird, amazing thing. We have fucked up a lot of stuff, but we have loved them really well.” 


I’m more convinced than ever that there is a strong, roaring river in our subconscious. It flows and moves and controls, whether we’re conscious of it or not. It holds the deep reservoir to our shame, our trauma, or fear, and also our true, beautiful, and brave parts. If ignored and neglected, the river will run our lives, and likely crash us on its rocky shores (it did me). If tended to, explored, accepted, and surrendered to, it has the power to move heaven and earth for good. The healing waters are within. We take our cars to get our oil changed, we take our teeth to the dentist, take your soul to a professional. They’re worth every penny. Actually, you’re worth every penny.  My key therapy takeaways in 2022:

  • Get Really Clear. Spend time getting really clear. On your life, your love, your career, your wants, your not-ok’s, your purpose, your path. Left to wander, we’ll meander. But with clarity, we’re magic makers. 
  • You’re OK. I’ve been doing neurofeedback for a couple years now, off and on. When I first settled into the chair and got connected, my therapist said I had what’s called, “hyper-vigilance” in my alpha brain wave every time I closed my eyes. At first, I thought it was cool. And then, I realized it’s a conditioned fear response that my brain fires smoke signals every time my eyes close, alerting my body that I’m going to be eaten by a leopard. My eyes dart, my brain activity jumps, my heart rate spikes. It’s been steady, laborious work, but my brain is responding. I’m reminding myself that I’m not at threat, that I’m safe, that I’m OK. 
  • Lead from Love. Not fear. We can connect in fear, sure, but it’s a frenetic, short-lived flame. Leading, connecting, and being curious about others from love is the way to lead. And live. 
  • Let Go of Your Should’s and Supposed To’s and Write a New Story. A lot to unpack here, but in short, the stories we’ve believed and lived are often ones we’ve picked up with a nice heaping of shame and performance based thinking. Identify where you say “I should” or “I’m supposed to” and at least question what needs to happen next instead of assuming you must. 


As men age, generally, their circle of friends get smaller. I’m aging, and I noticed this year, my circle is getting smaller. Not because I have less opportunities for cultivating the deep friendships I’ve formed over the decades, but because I’ve grown accustomed to investing in family, work, and myself. And my friendships have suffered because of my choices. I have one gut-level, soul connected friend I have conversations with routinely, and then a handful of others who I’m less regular or consistent with. I’m not happy with this reality, but it is the reality. I intend on choosing differently in 2023. Because I miss my friends. 


When I first thought about 2022 travel, I was bummed that there wasn’t much travel. I love travel. I love exploring new places. I feel free and at peace. As I reflected, there was far more travel than I initially thought, it just looked different. The highlights:

  • Spring Break in Florida. It’s become an unspoken tradition to get to South Florida most Marches and stay with Brooke’s folks in Naples, and we made it happen again in 2022. It was the first time in Guild’s 5-year history that I didn’t check email for an entire week. That, plus the fishing, plus the sun, plus the memories, plus the well, Florida, made it awesome. 
  • Few Basketball Short Trips. I got to accompany our second-oldest on a few of her out of town club and high school basketball trips. We went to Des Moines (and checked into the skeeziest hotel and immediately left), Dallas (that Jeep rental was dope), Ames (they got rolled), and Orlando (with her high school just this week, it was a hell of a time getting a flight after the SW debacle but a last-minute Spirit deal saved the day, and it was a wonderful 48 hours – minus the Disney trafficjams and nonsense). 
  • The Desert. We moved our oldest into college in Phoenix, then went back a few weeks later for our first Parents Weekend. We shopped, hiked Camelback, slept in a trendy hotel together, ate swanky meals, and even ordered our daughter a cocktail. We love Phoenix now. Especially when it’s not 110 degrees. 


The older I get, and the road of recovery I’ve embraced, there’s really no secret or hack or home run swing to cheat the life code. It’s a pretty simple, difficult thing. String together a bunch of good days. Or string together a bunch of apathetic days. Both produce compound results. We just get to choose if we want virtue cycles or vicious ones. A life well lived is a life lived well in the mundane. The habits I track (with streaks going both directions depending on the week):

  • Eating
  • Alcohol consumption (2 years sober as of January 1, 2023) 
  • Soul work (as I define meditation, journaling, praying, and/or reading depending on the morning)
  • Reading
  • Writing
  • Moving (more below)
  • Key Projects or To-Do’s
  • I still chew my damn fingernails. 


I’m in process here. My relationship with the church has changed significantly, but my relationship with God (as I believe it to be a Trinity of the Father, Son, and Spirit) remains a fundamental piece of my life. My aperture is widening from what I thought to be “absolute truth” a decade ago, and that’s mainly through experience with many who have been harmed, injured, or even abused by formal institutions. I believe God pursues our souls relentlessly, accepts unconditionally, and has written the greatest love story ever told. And he’s invited us into being agents and authors of this grand narrative. 


I’m two years sober from alcohol. If you want to know why, read this. I don’t miss having regrets, and I enjoy the clarity of mind without the fogginess of booze hanging around those vessels. And to be clear, I’ve been around alcohol plenty, and I have no judgement of those who drink. I’ve bought my own daughter a drink, ha. For me, this was a welcomed addition to my life, that’s all. 

Further, I’ve noticed that from August to November each of the last few years, I pack on some unwanted weight. I legit think there’s something in the scarcity resources of my subconscious that feel the need to prepare for winter, and hunker down a bit. This year, thanks to my neighbor Eric’s evangelizing, I began 75HARD the day after Thanksgiving, and judging from my meat coma and love handles on the Day One pic, it was time. I’m 37 days in, not making a big deal of it, but it’s been amazing to get moving, get clear, and follow some rigid restrictions (that lead to freedom, see above on constraints). 

When I’m humming, my eating plan these past couple years, and more specifically for 75HARD is pretty simple:

  • No alcohol
  • No sugar (not in a freaky way like looking at ketchup ingredients)
  • Plant powered (eat lots of veggies, fruits, nuts, beans, seeds, grains)
  • Don’t eat after 8pm
  • These things combined with consistent movement, just always work. 
  • And goodness, I’ve fallen in love with walks this year. Walks solo, walks with Brooke, just walking in general mixed in with my running routine has been so great for my soul. 


A few catch-all thoughts, learnings, and meanderings:

  • You are enough, and there is enough. Scarcity is a fabrication of our fear. We are enough in and of ourselves, and the resources available to us, in this moment, are sufficient. We don’t need more to be happy. 
  • No amount of eating shitty-for-me food feels as good as I think it will when I’m done. 
  • No one has it all figured out. 
  • The simple act of taking a deep breath, and paying attention to said breath, diffuses lots of things that are better left unsaid. 
  • Music is medicine to the soul. 
  • Most of the time answering a question posed to you with a question of your own back to the original asker  is the quickest way to connection and clarity. 
  • Have a bias towards action, it gets you out of your head, your feelings, and excuses, then provides evidence that’s real that you can respond to instead of living in anticipation of it. 
  • The cheapest form of payment is often the most satisfying: paying attention. It’s incredible when we get out of our heads and into the moment, what we’re able to witness. 
  • It’s tough out there. Smile at someone, tell them thank you, tell them they’re doing a great job. 


A few books and podcasts that have been helpful for my journey this year.

Mackelmore, send us into 2023. 

“I’m sick of missin’ out, sick of the fear and doubt

I’ma get spiritual soon, live in the here and now

Alone in my room, but you gon’ hear me loud

And clear, let’s start it at the top of the year”

Next year’s gonna be better than this year. And 2022 was a wonderful challenge.

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