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What's the Worst that can Happen?

I spend a lot of time walking with people through the question, “What’s the worst that can happen?”


That’s where probates come in, when things don’t go as planned — and it’s my job to help people prepare to prevent that. But the what ifs, all the talk of planning and prevention, really center around one thing: preparing for the unknown. Because the truth is, no one can predict exactly what will happen in the future. And that’s uncomfortable.


It used to make me feel panicked not to have a clear path forward, a plan for the future.


When the Air Force recruiter asked me back in 1998, “Where do you see yourself in five years,” I wasn’t sure. And to be honest, that was kinda terrifying. I ended up being in the Air Force for 16 ½ years before the opportunity arose to retire early – which presented a whole new set of fears that we’ll explore in more depth as we go. But when you’re in the military, you know where you’re gonna be at any given point — there’s a routine and a comfort. The stresses of military are different: Are we going to war? Am I going to be deployed? Am I going to get an assignment somewhere I’ll absolutely hate? But in the end, you’re just gonna go where they tell you to go, and you’ll find a way to make it work. It may sound crazy but there’s a certain comfort in that.


Getting out of the military was much harder for me than I had anticipated. After the first 4 years, I just assumed I would be in 20 years. Because, why not? But then, late in 2013, it was announced an early retirement program was being offered for those who had served more than 15 years but hadn’t quite reached retirement. Given the numbers in my field, and other factors, I submitted my application for early retirement. It wasn’t until I actually received my retirement orders in hand that it actually hit me…it was really happening! And, I’ll tell you, it was like a gut punch. I remember speaking with one of my favorite mentors, Chief Divina Riley, about the whole transitioning process and just the feelings involved with all of that, and she looked at me and smiled as she said — yes, leaving the Air Force is going to include a grieving process. After all, aside from my relationship with my parents, the military is the longest and most impactful relationship I’ve had in my entire life, to date. She promised it would all turn out just fine and that it’s gonna be okay because it was my choice to leave. Sadly, Chief Riley was later killed in a car accident in October of 2015. I never got to tell her that she was right but I’m guessing she already knew.


But the reality is, people don’t like endings.


So, yes, I was leaving the Air Force on my own terms, but still…I had a hard time “breaking up” with the military. Suddenly I didn’t know what I was going to do next, and there was no one to tell me where to be or when to be there. The lack of a plan and the vast number of decisions and options open to me was more than overwhelming.


See, people look for comfort in things. When you walk into a crowded room, you look for someone you know, or something familiar, some common ground upon which you can stand with someone else. That’s how people deal with stress — they look for comfort.


But then I entered law school. And I fell back into what was comfortable. That was, routine, classes, a schedule. But when that ended, there was that same old feeling again — panic.


The fear of the unknown.


When clients come to me, they often don’t know what to do or what comes next. They may have dozens of decisions to make, no clear path forward, and all the paperwork they’re reading is written in what feels like a foreign language. Add to this those emotions are often high because they’ve just lost a loved one, or they have a complicated life situation, or a new life circumstance, or something’s at risk — those are moments of stress. Moments of so many unknowns. Moments of panic. I totally get that. I truly do.


And now, I get to be the one offering that comfort. That common ground. We’ve all felt confused, sad, or angry. I can identify with every bit of that. Fortunately, I can say, “I understand what you’re feeling; here’s how I recommend we make it better.” I can interpret that “foreign language” learned in law school and explain it to my clients in a way that’s not as confusing. I can provide a long-term view and help them lay a road map, so that when the time comes to use those plans in the future, they aren’t panicked. They have a clear path forward. They are prepared, and they have a plan. I can put them at ease: It’s gonna be okay.


It’s even better if we can make that plan far in advance, before the worst happens. If we can protect a client’s family and assets through preparation with a plan that covers the future what ifs, it’s almost always gonna be okay.


Even in the unknown, I think we can agree there’s comfort if you know it’s gonna to be okay, that everything will work out. And knowing that can remove so much of the stress.


Next month, I want to build on this idea by expanding on a famous Ronald Reagan quote, telling you a bit about my time working with explosives in the military, and discussing how — for me — working with my clients is all about creating calm rather than inciting fear.



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