Most people come to retirement planning with a technical question. Should I do the Roth conversion? When do I start Social Security? Pension or lump sum?
Those questions are real. But when my dad Shawn and I sat down with Roger Whitney on The Decidedly Podcast, he made a point I keep coming back to. The technical questions are usually the least interesting part of the plan.
Roger is a retirement planner in North Texas, and for years he held office hours where people could book 20 minutes with him just to talk through an issue. Over hundreds of those conversations, he noticed a pattern. People would show up with a Roth question or a Social Security question. Then he would start asking questions of his own, and it usually turned out they were looking for permission to do something they already knew they wanted to do.
There's two retirement crises. One is the real one: people don't have money. ... But there's another crisis with people that, out of luck, work, happenstance, have the resources, that are scared as heck and can't give themselves permission to live. There's a crisis of confidence.
A light switch or a dimmer?
Part of the fear, Roger said, comes from how we picture retirement. We think of it as a light switch. A business owner sells the business, and the next morning the question is: now what?
Very few people see it as a dimmer switch, with a lot of room between the two extremes. Roger thinks there is a lot of gold in that middle ground.
There is also the loss of what he called the reward cycle. If you have built a successful business, you know the feeling. You can create something out of nothing. You can recover from a bad call by working harder. When you retire or sell, those feedback loops go quiet, and the confidence they gave you can go with them.
Dad made a point here that stuck with me. It is rare for a money decision to be both irrevocable and impossible to recover from if it goes wrong. Plenty of decisions feel that way, though, and people can spend months debating a choice that is one option out of several reasonable ones.
Retirement planning starts with vision.
Roger organizes every plan around four pillars, in a specific order:
- Vision. What do I want? He starts with your top 10 values and builds goals from them. And he holds it loosely, because the answer will change many times. It is written in pencil.
- Feasible. Is it possible? You organize your social capital, your human capital and your financial capital, and test whether the journey works with the resources you have. In most cases you can't have everything, so you negotiate with yourself.
- Resilient. If a storm comes, does the boat stay afloat? Roger said this is where a lot of planners fall down.
- Optimize. Only now do you look at enhancing the journey. This is where most of the technical questions live.
When someone brings Roger a Social Security question, he frames it first: this is an optimization question. If the plan is already feasible and resilient, that choice does not carry the weight it feels like it does.
What stood out to me most was the resilience pillar, and that it comes before optimization. It is an overlooked step. Instead of losing sleep over optimizing Social Security, the goal is a plan sturdy enough that you are not losing sleep at all. Then the details can be fun.
Skip the bling.
I had a golf lesson the day we recorded this episode. If I want to get better at golf, the easy move is to buy new clubs and a golf watch. It feels like progress. The hard work is learning to turn my wrist while working the hip and keeping my arm straight.
Roger calls the shiny stuff "financial bling." It is the fancy strategy from an article or an ad, and it is usually what people bring to the first meeting. The foundation work is harder, but he has found that when you start in the right order, decisions get easier because they flow from the work you have already done.
That fits the word itself. To decide comes from a root meaning to cut off. Each pillar cuts away options, so by the time you reach the technical choices, you are only weighing a couple of them.
Know your commander's intent.
Roger borrowed an idea from James Mattis's book Call Sign Chaos: commander's intent. In his example, the order is to seize a bridge in order to stop a retreat. The real objective is stopping the retreat. The bridge is only a tactic.
Retirement planning for business owners works the same way. Dad pointed out that when you ask people what they want to do after they sell or retire, the answers tend to land on travel and golf. Getting clear on the purpose that is pulling you forward is a much harder question, and it is the one that shapes every decision after it.
You don't have to have it all figured out.
For years Roger told people it was healthier to retire to something than from something. He has since revised that view.
Sometimes it's okay just simply to make the pain go away, because sometimes we can be in a position in a corporate world or in a business where there's no way I can figure out who the heck I'm going to be, because my mind is so in the mosh pit of the operation. Sometimes you just have to go create the space and trust that you'll figure it out.
The old framing had a cost. Roger heard from people who worked an extra year or two because everyone told them they had to figure it out first, and they hadn't yet.
A friend of mine once put it this way: being indecisive is not the same as being undecided. You can be undecided about your next chapter and still move forward with a plan to learn what you need to learn.
Roger also uses inversion. Instead of asking what you want five years from now, ask what you don't want. If you don't want to be in meetings around the clock, what has to be true in your business for that to change? Then you work backward into the goals.
What this means for you.
Whether you are planning for retirement, a sale, or both, a few ideas from this conversation apply:
- Start with what you want, in pencil. Your vision will change. You only need a starting point.
- Build resilience before you optimize. The technical choices matter more once the foundation is in place.
- Leave room to pivot. Roger pointed out that one-way decisions are the hard ones. Buffers, like cash reserves, give you room to adjust.
- Organize your thinking. Roger uses the OODA loop from aviation: observe the facts, orient around what you are really solving for, then decide and act.
As Roger put it, most questions in this area come down to a judgment call. The goal is to think it through in an organized way, so you can feel confident you didn't just wing it.
Start the conversation.
If you are a business owner looking for a retirement planner in Fort Worth, or just a sounding board for what comes next, I'd love to have that conversation with you. Book a free conversation and let's talk about your five key decisions.
This article is based on a conversation from The Decidedly Podcast. Insights, advice, and comments provided by Sanger Smith, Shawn Smith, and guest speakers should not be considered personalized financial advice or recommendations. This content is produced solely for informational and educational purposes. For personalized guidance, book a free conversation.
