I want to take a moment to attend to gratitude. I focus my attention on addressing the worries and concerns of families; sometimes as a planner, other times as a crisis manager. An unfortunate effect is that my experiences sometimes lead me to dwell on roadblocks, speed bumps, and negativity. And that’s kind of a bummer.

It also disrespects the great fortune I have at being able to do what I do, to live where I live, and to share my business and recreation with people whom I care a great deal for. So I find it helpful to periodically pause the to-do list and business planning and case management and recharge with moments of reflection on the stores of energy and resources I’m lucky to have so readily available.

And writing about how I’ve been sitting here reflecting on my gratitude serves as an accountability partner on keeping me focused. The whole reason I believe in and commit to our Less Worry | More Happy trademark is because living like we’re supposed to depends on our ability to conquer fear. And acknowledging and being thankful for having and being more than enough is a weapon in overcoming worry.

Defensive Coordinator

Although often mistakenly considered just a “money thing”, real wealth management expands its attention from merely financial capital to include a larger mix of things that contribute to the full scope of a Life Portfolio (I strongly recommend reading The Wealth Creator’s Playbook for an examination of this concept). And for those who value partnership in “growing” their Life Portfolio toward a desired outcome, there are wealth management firms all over the place wanting to help you get there with a financial and wealth management plan.

But what is rare is the dedicated expert who plays the role of defensive coordinator to that plan. What I’m talking about is a person whose sole job is to see where the plan might be specifically at risk, to influence the extent of its impact, to allocate finances toward prevention and recovery, and to direct a crisis toward restoration. It’s rare because although the best opportunity for someone performing that role rests in the intimate relationship people have with their wealth manager, the proclivity of an expert who can do the best job exists in another industry where people get paid for selling a product instead of stewardship.

There are 3 reasons why this needs fixing. First, and sadly, bad days do happen. Optimism bias, which explains how we underestimate our exposure to loss, is a real thing. Understanding our true exposure to risk is important because naiveté and ignorance are not effective or mature. Second, the paradigm of being referred to an insurance agent as the defensive effort is grossly insufficient for reasons I’ve mentioned many times. Insurance is a wonderful financing tool for limited negative experiences, but it provides no avoidance, mitigation, or control and it rarely lives up to expectations. Insurance alone will almost always disappoint. Third, the landscape of modern risks facing families is evolving and expanding. Yesterday’s problems aren’t today’s problems and the glimpses we’re getting of emerging risks is even more complex and severe. So I’m going to bet that whatever process you think you follow to defend your wealth plan today will need some updating.

Our trademark is Less Worry | More Happy so we don’t believe in fear mongering. But we do believe that being intentional and sophisticated about how your plan might be interrupted by an unfortunate event, lawsuit, or an unscrupulous person is rooted in sound values. And in my work with families I’ve yet to find someone who doesn’t feel at least a bit of liberation from worry and more free to pursue all the abundance of their Life Portfolio because they’ve taken a step forward with a defensive component to their plan.

Our Best Hope

Insurance provides some money to pay for some things on only some bad days. If it is your primary risk management strategy, it is insufficient and inefficient.

Between policy changes, eligibility restrictions, deductible changes, sub-limits, and non-renewal postures, the availability of insurance coverage is shrinking. In the meantime, modern risks that normal people face like home renovations, domestic-employee hiring, cybercrime, electronic aggression, shared-economy use of assets, micro-livery occupations, multi-generational home occupancy, severe weather, and at-home employment are expanding. The gap between what insurance wants to do and what a family needs is growing.

Add to that a steady industry decline in attracting, training, and retaining talent that can consistently deliver a consumer experience that people are used to getting elsewhere (we still expect people to sit on hold for minutes upon minutes to get help, to wait for two days to get a return email, to have claims authority centralized to one person, to mail consumer unfriendly notifications of premiums or policy changes), it’s no wonder that I’m worried.

Will a consumer’s experience with their insurance be better tomorrow than today? It’s a fundamental question that you’d think would be a cornerstone of the industry’s strategic plan to answer. Yet companies talk today about the same streamlining and improved communications and efficiencies that they were talking about when I started 31 years ago. New techniques and new technologies, but same plan. The industry has said the same “communicate better, report faster, resolve happier” forever and how have they done, generally?

And all the while, what insurance companies want the most is your business. So they produce low-level commercials that avoid much content and they visit my office and try to grab more shelf space. But what they won’t do is re-invent. Insurance is what it is and it is not a mature approach to addressing the risks you face if it’s your sole hope. It should be a component of a plan, not THE plan. All day long I ask people why they are spending $1.30 to pay for insurance on things they could resolve themselves for $1.00, or prevent altogether for $0.50. There’s work that can be done so that you won’t need to use your insurance in the first place. Not having the bad day is always better and collectively, if the need for insurance decreases, the competitive pressure to attract you to them will increase. It’s our best hope.


The typical approach to managing risk in a family is one best described as Respond & Recover. The whole insurance industry is predicated on the value of this approach as it supplies products and professionals dedicated to putting families back on track after a loss event. And this paradigm is ingrained into the expectations of consumers and their advisors to the point where insurance is seen as THE risk management option available.

But a complementary approach to managing risk in a family should be one that I’ll describe as Predict & Prevent. There should be an overwhelming push to build an ecosystem of products and professionals dedicated to stopping the bad day from happening in the first place.

Fortunately, I believe a wave of change is coming in that direction so that the new paradigm for managing risk in a family will incorporate both. Markets love efficiency and not losing is more efficient than recovering from a loss. Technology and sensitivities to Big Data that drive the arbitrage within the insurance industry can be flipped to the prevention market where there’s profit from behavioral change. And if presented an alternative, consumers will prepare an answer to the question, “how much would you spend to not spend money on insurance?”.

Practically speaking, this movement should come from the insurance industry where the experience and proclivity to be concerned with family risk lends itself best to adding a Predict & Prevent mindset. Very little investment would be needed if those in the insurance business shared this vision and expanded where they need to go. But economic vacuums will be filled by someone else if the sacred cows of “the way things are” aren’t dealt with.

A car company changed the energy market, an information company changed brick & mortar shopping, a consumer electronics company changed the music industry, and a philosopher(s) might be changing centralized finance as we speak. None of these disruptions spelled the end of the original market, but the biggest winners were the outsiders who didn’t invent the mechanisms of their movement, but merely applied them to the vision that “this is better than that“. I bet the original insiders in those markets wish now that they’d been their own disruptors. And as I predict that someone will be successful selling the vision that prevention is better than reaction, we’ll see who that someone will be.

Non-Transactional Mindset

Transactional relationships are potentially ruinous because they hide what you aren’t getting behind stuff that doesn’t matter. The game becomes winning the transactional experience, not providing something meaningful. The worst: you pay us less to give you something you think you have to have. Second worst: I want good customer service. The reason these are wrong is because if I can convince you of these two, you may not think to realize that you’re buying garbage.

Proof? There are two insurance commercials on TV today that promise low premiums while using examples of scenarios not even covered by the policies they sell. That’s unbelievable to me. And one of the highest rated insurance companies out there has some of the biggest gaps in coverage.

I think the overarching lie is that defending your family against potential financial calamity can be solved by making a purchase. No. Defending your family starts with a list of thoughtful questions, not your checkbook. Defending your family depends on a plan that you’re involved in making, not something that comes off the shelf and handed to you. Defending your family depends on wisdom gained, not by falling for superficial gimmicks.

I think insurance is important and I’m not critical of the product. But there needs to be someone championing the truth that buying insurance is incomplete. It doesn’t prevent the bad day, it doesn’t answer when it’s better to NOT buy insurance, it doesn’t offer anything until you have the bad day, and it’s limited in the scope of help it can provide. The insurance transaction is just playing a role, not telling the whole story. So look instead for either a more complete relationship from your insurance expert than just a transaction, or find a complementary relationship that can do more than the product can.

Favorite Questions

What events could move my financial plan out of alignment? What are the probabilities of those events happening? Can my behaviors or circumstances influence those probabilities?

What are the smallest possible changes I can make that’ll have the greatest impact on my exposure to risk? What’s the largest possible return on the smallest possible investment?

How resilient is my financial plan to loss? How much financial horsepower do I have at my disposal for recovery? How can I influence the parts of my financial plan that will need to be sacrificed?

How can I use the confidence gained in answering these questions to better align myself with my current and future plans? How does taking action in this area serve as an accountability partner to how I say I want to live?

Agency of the Future

We aren’t counter to the digital future, but our passion is committing to the deeper personal connection put more at risk because of it.  As technology completes more of the tasks needed for a working relationship, we’re devoted to the emotional relief of worries and stresses that families face in their scarce-resource decisions. 

No family we know would say that technology has made our industry more easily understood, less complicated, or less volatile.  No family we know would say that they expect insurance of the future to be more personal.   No family we know would say that technology is making our industry more aligned with their family needs.  Innovations that make it easier to transact or communicate is not the same thing as making things more valuable. 

And what our clients report as most valuable is their ability to lean on someone with a deep expertise and a genuine interest in what matters to them so that their decisions and following behaviors are allocated accordingly.  Do we invest in technology?  Sure, but we see it as a price of admission to be worthy of being in this business, not something around which to build an overarching strategy. 

We believe the agency of the future will decide to go in one of two directions – either an accumulator of transactional relationships, or a thought leader.  And we’ve chosen to be the latter, filling the space to show that the emotional benefits of taking steps to protect the family outperforms the best insurance transaction experience. 

We sell and service our share of transactional relationships, but our future hinges on the relatability of a wider offer of defense-mindedness that permeates financial plans, safety concerns, raising children, and the pursuit of living as one is called to live.  Because addressing worries liberates one to pursue things that are good.  And we’re good at the day that ends with clients saying, “Wow, we never knew that. This feels so much better.”

We fully expect to diverge more from our peers in the future.  We intentionally slow down the decision-making process, we intentionally step away from selling policies if it’s not the best fit, and we invest heavily in our professional gravitas.  So we think we’re the agency of the future because we have no desire to look like any sea change or like anyone else. 

Barriers = Bad

There are two reasons to address risk. The first is to lose less, the second is to live more. The mission for both is the same – to remove barriers that are standing in the way of living the life to which you’re called. There’s nothing noble about losing less if you keep living a small life.

So there should be an envisioned result from any input you make.

  • If you could remove the one thing you worry about most, how would your life be different?
  • What would you do with your energy if it weren’t devoted to that worry?
  • How would you spend your time and money differently?
  • Who would notice a difference in you?

Answer those first and then build a plan to move it toward reality.

Best Day

The first thing that popped into my head this morning was the realization that I own more TVs than there are number of times per week that I reach out to my closest friends. Which made me think about how much effort I apply toward holding onto and protecting things and opportunities I think are good for my family, yet which one of us wouldn’t place a higher value on our time and relationships?

The consequence of unchecked rugged individualism is relational poverty and tribalism. It seems we’ve been infected with an acute illness of “us” vs. “them” on pretty much every subject, and forced isolation because of the pandemic and distrust in pretty much everything about everything doesn’t help to build community, obviously.

And yet…our youngest daughter got married this weekend and I received a heavy dose of overwhelming contentment seeing how much everyone there enjoyed each other. Two families, multiple groups of friends, all there showing love to the others. So I don’t know how to address the big issues, but maybe addressing my own weekly behaviors to be more affirming, more outgoing, and a more intentional listener will at least make me and my own tiny corner of the world a bit more tolerable.

And it relates to my profession because as I work with families to do exactly what I reflected on (protecting things and opportunities that are good for their families), I’ll fight for nobility believing that doing those things well will liberate someone from worry so they can use their excess to find happiness in the connections with other people.

30th Work Anniversary

The only thing I’ve ever done in my career is concern myself with the defense of families’ financial wellbeing. I’ve given counsel and helped families plan contingencies for occurrences that might interrupt their financial plan. And I’ve been there as a financial first responder when a really bad day happens.

So in my 60,000+ hours of doing just one thing, I’ll share some earned observations:

  • Optimism bias is alive & well. My biggest competitor is apathy & the belief that bad stuff happens to other people. No one I’ve known has ever said after a loss, “yup, I saw that coming”.
  • There is an overemphasis on insurance and not enough on risk management. Insurance is a product that does nothing for you until after something bad happens. Risk management considers making the bad day not happen or result in less of an impact if it does. Most families and most wealth advisors think good insurance is good enough. It’s not.
  • I’ve never once heard after a claim, “that was a good experience.” Investment in prevention is worth way more than the best possible post-loss response.
  • Core competency and an interest in addressing risk in the body of a fiduciary engagement (within both in the wealth mgmt and the insurance industries) has diminished.
  • People place too much importance on frequency and not enough on severity. We’re drawn to worry about the more common things, and we should instead be drawn to the things that could be most ruinous.
  • Families love to learn. The best decisions are made when the full story is told and my best days are when someone says, “Wow, I never knew that. That helps us a ton.”
  • Risks are evolving. Trends in losses due to weather, wildfires, cybercrime, reputational attacks, professional liability, libel/slander/defamation mean yesterday’s approaches to wealth defense are outdated.
  • More frameworks for addressing the process of risk management are needed. Ad hoc (at best) approaches are outdated. Analytics and formal frameworks based on your specific behaviors will be the future.
  • It matters who you listen to. From whom you take advice today magnifies the result of tomorrow.
  • There’s a tremendous opportunity for wealth managers and insurance advisors to reinforce the emotional benefits of making investments in behaviors and plans that defend a family’s financial wellbeing. Perhaps that’ll be something for me to tackle over the next 60,000 hours.