April always feels a little gentler to me. Not slower, exactly. There is still plenty of noise: markets moving, headlines shouting, tax deadlines looming, calendars full. But there is usually a subtle shift in the air this time of year. A bit more perspective. A bit more light, and I’m not just talking about the sliver of sunshine still hanging around when I leave the office each day. A reminder that just because something feels urgent does not mean it is ultimate.
That matters in life, and it really matters in financial planning.
People want clarity with money. They want to know if they are on track, if they are making good decisions, if a plan will hold, and if they are going to be okay. I get it. I sit in those conversations all the time. And while there are absolutely moments for precision and rigor, one of the most important truths in planning is that the future is under no obligation to cooperate with our projections. That is not a reason to avoid planning. It is the exact reason planning matters.
I was recently listening to The Psychology of Money by Morgan Housel while running along the water on Roosevelt Island in NYC and savoring the fresh, if fleeting, spring weather. One section stopped me in my tracks. It put words to something I think planners know well, even if we do not always say it this clearly.
“What’s the saying? You plan, God laughs. Financial and investment planning are critical because they let you know whether your current actions are within the realm of the reasonable. But few plans of any kind survive their first encounter with the real world. If you’re projecting your income, savings rate, and market returns over the next 20 years, think about all the big stuff that’s happened in the last 20 years that no one could have foreseen: September 11th, the housing boom and bust that caused nearly 10 million Americans to lose their homes, a financial crisis that caused almost nine million to lose their jobs, a record-breaking stock market rally that ensued, and a coronavirus that [shook] the world…
A plan is only useful if it can survive reality. And a future filled with unknowns is everyone’s reality.”
Exactly.
A financial plan is about making thoughtful decisions now, while knowing full well that life will almost certainly change the script.
Five years ago, I moved into my own place for the first time in my life. I was thrilled to hit that milestone until I realized how lonely it could feel. Coming home to my quiet corner of Queens felt strangely far removed from the bustling city I have loved calling home these last fifteen years. So, I got Henry, my shih tzu and best friend.
Before I brought him home, I read the dog-parent equivalent of What to Expect When You’re Expecting. It walked through the costs I should plan for: food, toys, grooming, routine vet care, a cushion for shots, and the occasional surprise. Helpful? Sure. Complete? Not even close.
What it missed was real life. The endless refill of poop bags and treat jars, because apparently, one eleven-pound dog can live like a linebacker. The wipes after he walked on grimy city streets and before he hopped straight onto my bed. The toys that somehow needed replacing every five minutes. And what it definitely did not prepare me for was the fact that Henry would have crazy shark teeth and, at four years old, need dental surgery that cost me several thousand dollars.
That does not mean planning for Henry was pointless. It means the first draft was never going to cover everything. It caught the obvious stuff. Life filled in the rest.
I have seen the same thing play out in my career. I did not join TBG with a grand plan to become a financial planner. I come from a music and theatre background, and my opening months here were spent overseeing alternative investment paperwork, helping with the client portal, and soaking up everything I could. Then one resignation, one unexpected opening, and proximity to eMoney changed the trajectory. I got the chance to shadow, learn, and step in.
What happened next is the part no one could have fully mapped out. Clients came in focused on investments, and rightly so. But planning deepens trust, and trust widens the conversation. Before long, you are talking about retirement, taxes, estate plans, family decisions, risk, generosity, and all the other things that make money personal.
I keep coming back to this pattern. Many of the most meaningful parts of life and work do not arrive with a clean blueprint. They grow because we pay attention, respond, and make space for what matters.
A plan that only works if everything goes right is not much of a plan. Housel makes a compelling case for room for error. I would not argue with him. But because I am, to my core, an “everything happens for a reason, God makes no mistakes” optimist, I’d just personalize it: room for life.
Not just room for disaster. Room for maintenance, inconvenience, and the slow, steady, unglamorous costs that come with being a person, maybe owning a home, raising kids, caring for parents, loving a dog, growing a business, or just living in the world as it actually is.
Room for life means a surprise does not automatically become a crisis. It means a setback does not instantly force a bad decision. It means your financial framework has enough flexibility that real life can happen without knocking the whole thing over. That kind of margin is not flashy. It may even look a little boring. But I will take a plan that gives it over one that looks perfect on paper every single time.
That breathing room matters. Build a plan that can bend without breaking. Build a plan that leaves room for life. Not because life will go wrong, but because life will be real.
Matthew Gregory
Director of Planning
Trevor Cummings
PWA Group Director, Partner
