Road to Launch with XYPN Member Alan Skillern, CFP®, MBA

“To affect the quality of the day is no small achievement.”

Fortune Cookie

Mondays at noon, I trade spreadsheets for sippy cups and market reports for Mickey Mouse. As a financial advisor running a one-man practice in rural Indiana, I never expected my weekly schedule to revolve around a 15-month-old who calls me 'Allie.' I'll admit that in the very early days of my firm’s launch, I resented these hours. I had so much anger about tiny forks, cartoons, and the chaos of meal times when I could be working. 

I questioned whether I could be both the professional I aspired to be and the uncle she needed. But somewhere between diaper changes and client calls, I discovered something unexpected: these Monday afternoons aren't just an obligation—they're teaching me patience, perspective, and priorities in ways my financial training never could. 
So my office closes at noon, but something else opens up.

Best Case Financial 

I’ve spent the majority of my career working at fee-only RIAs. I don’t have a wirehouse/broker-dealer horror story. I’ve never sold a product or taken a commission. I built, maintained, and presented financial plans for $100 million in AUM at my previous firm. 

Here are notes that I received from the advisors I’ve worked for over the years:

• “You do good work, but you’re not in the office when the other guys are.”
• “I know you are working the hours. I see you working late at night, but I just want to see you get through things faster.”
• “I know you hit the benchmark we set for your promotion, but we just don’t think you are quite there yet.”
•  “You are so lucky you didn’t have to build a business and eat what you kill. You should be more grateful.”

Well, now I eat what I kill. 

In December 2023, as winter settled over Indiana, my world shifted on multiple axes. My niece had just been born, bringing a fragile new joy into our lives. Then, a week before Christmas, suicide took a beloved family member. My wife and I were struggling to hold everyone together while privately nursing our own wound: the devastating news that biological children weren't in our future. The weight of these converging realities was crushing.

It was in this raw, vulnerable state that my employer chose to deliver threats via ChatGPT—a moment so jarringly tone-deaf that it crystallized everything. I realized how fundamentally incompatible my job was with being truly present for my family when they needed me most. So I quit—right there, in the wreckage of that week.

Some decisions aren't made—they simply emerge as inevitable truths. Standing amid grief and uncertainty, with a two-year non-solicit hanging over me, no liquid assets, and sitting in the wake of tragedy, I chose independence. I named my firm—Best Case Financial—opened an LLC, and commissioned a logo from a designer on Fiverr—a logo I still love deeply. (I recommend using XYPN’s checklists to make sure your firm name is acceptable.) 

I ordered custom stickers of that logo for five dollars. Such a small thing, yet holding them in my hands became unexpectedly powerful—a tangible anchor in a storm of intangibles. Each time I touched one, it reinforced the new reality: I was now in the driver's seat. Sometimes, when rebuilding a life, you need something physical to grasp while everything else remains in flux.

Looking back, I didn't just start a business in those dark December days. I reclaimed agency at a moment when life had stripped me of so much control.

The Long Wait

2024 unfolded as a year suspended between worlds. In our Indianapolis fixer-upper—the one we'd poured ourselves into since 2018—I had just completed the crowning achievement: a custom-tiled ensuite bathroom that represented years of sweat equity and midnight renovations. The house finally stood finished, a testament to persistence. That's when my wife pitched that we should move back to our hometown, closer to both our families. The timing felt prophetic.

Let me be absolutely clear: none of this would have been possible without my wife. Not my independence and not our survival during this transition. Her CPA expertise kept us financially afloat while I navigated the uncertain waters of entrepreneurship. More than just financial support, she offered a kind of unwavering belief and clear-eyed perspective I needed. When I questioned everything, she questioned nothing about my ability to succeed.

What we didn't realize when purchasing that modest fixer-upper was that we weren't just building a home—we were building our future freedom. It’s crazy to say, but the best thing I have done for my financial well-being was buying a fixer-upper. The equity we built has opened so many doors for us and became the financial runway for my firm. There's a profound irony here: working double shifts—at my day job and then coming home to renovation projects—is not for the faint of heart, but it ultimately freed me to build my schedule. I can't recommend this path strongly enough for those with technical skills and realistic expectations about the time commitment.

Throughout 2024, I existed in limbo. Waiting for our house to sell. Dividing time between caring for my niece and my wife's youngest sister. Helping my grandmother work through the estate of her late husband. Every day felt like standing on a launch pad with engines rumbling but no clearance for takeoff—a familiar feeling throughout my career. 

But this time, something profound was different. This time, I wasn't sitting in the second chair. This time, the countdown was mine to call.

As I navigated this transition, XYPN remained my constant north star, steadying me through the uncertainty of 2024. XYPN was there every step of the way, which I found both exceedingly rare and not at all surprising. My relationship with XYPN stretches back to 2017—the year I first dared to imagine having my own firm. As a graduate student with empty pockets and zero experience, stories of advisors building from a place not so different from my own were inspiring. Their resources kept me sane when the path forward seemed impossible.

The "Preparing to Launch Roadmap" became my lifeline, along with a dozen other resources provided by Chris Johnson, Senior Manager of Business Development at XYPN. Chris was incredibly patient as I repeatedly pushed back my timeline, never making me feel like a failure for needing more time. He offered additional resources in every interaction that better prepared me for registration. 

By the time I was finally ready to hit the big “GO” button, I found it was far easier than I expected. I spent hours worrying about registration and my ADV filing. I joined XYPN on 1/17/2025, contracted with their compliance team for my initial registration on 1/27/2025, and registered my firm in Indiana on 2/10/2025. Three weeks from commitment to completion. The mountain I had imagined scaling was a series of manageable steps, each bringing me closer to independence with less resistance than I had prepared for.

And then, just as fast as I built momentum, I was tripped up again.

Not by paperwork or regulations: I had failed to consider what kind of firm I wanted to run.

I knew all the buzzwords—fee-only, lifestyle practice, fiduciary—but when it got down to it, I still had a corporate mindset. The chip on my shoulder from years in traditional firms caused massive friction. I caught myself viewing my family obligations as interruptions to "real work." My niece's needs, my family's grief, and our home transition—were inconvenient obstacles.

I felt like a failure. Every hour spent helping my grandmother with estate paperwork instead of prospecting felt like falling behind. The voice in my head that judged my worth by billable hours and client acquisition wasn't even my voice. It was the ghost of every supervisor who had measured my value by my output alone.

I needed to talk to other people. It started when I was talking with my wife about how I was feeling. She pointed out that I acted like my work was the most important thing in my life. Digging into it, she asked me to imagine what my life would be like if I didn’t have any responsibility outside of my work.

The answer materialized instantly—empty, sterile, and purposeless. What would success even mean without the people I'd built this firm to serve and protect? Who would I be without the messy, beautiful chaos of Mondays with my niece or evenings helping the family navigate loss?

The Fortune Cookie 

It crystallized over Chinese takeout, of all places. I've always had good luck with fortune cookies—maybe it’s a horoscope thing, and you just see what you want to see. But my fortune read: "To affect the quality of the day is no small achievement."

Eight words that drove home why I was starting a firm. 

For months, I'd been measuring myself against the wrong criteria for success—like a character from "The Bear" with an evil chef in my ear telling me to go faster, do more, and be better. I had escaped my corporate job physically but had brought its metrics with me. 

I finally understood what my wife had been telling me: I'm only a failure if the only value I create is at work.

I love our profession. I love helping people so much, and I believe the work deserves our full effort. But never once has a client told me I wasn’t working enough. That’s noise that we have made in our own heads. 

I also benefited from talking with a fellow XYPN member who was launching a firm at the same time as I was. Mark Rosinski and I have been able to compare our registration experiences, tech providers, and just general vibes which has been enormously helpful for me. He cheered me on when I had my first prospect meeting and helped me adjust my firm growth expectations (whether he knew it or not) by discussing what he was doing and what was working / not working for him. 

I’m far from having everything figured out, but I’m okay taking my time if it means what I build is sustainable. Slow is smooth, and smooth is fast. I’m working to develop a firm that supports my family, not working to create a family that supports my firm. I hope that if you are thinking of leaping, you dare to do it how you want. I hope you stand and say, “My work can be important, but it may not be the most important thing in my life.”

 To the girls who call me Allie, my lovely wife Gwendolyn, and everyone else I care about so deeply, to affect the quality of your day is no small achievement.