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The Vehicle is Not the Destination

Cover image of the movie "Planes, Trains & Automobiles"

Vacation planning principles apply to your financial journey: The 6th Mistake

“Imagine that you had to drive from NYC to Los Angeles. You’re in downtown Manhattan hopelessly stuck in traffic. Bicycle messengers are whizzing past. You jump out of your car, sell your car on the spot (at a ridiculously low price), buy a bicycle, and continue your trip to the West Coast.

As absurd as this scenario sounds, investors do it every day when they make short-term decisions for long-term journeys. Stick with a vehicle that will take you to the end of the road.” -Don Connelly

If Peter ever elects to put out a second edition of The 5 Mistakes Every Investor Makes and How to Avoid Them1, I’d like to request he include Number 6: Mistaking the Vehicle for the Destination. When was the last time you planned a family vacation strictly by the mode of transport? Shouldn’t this only be considered after you decide where you want to go? Why is it that so many investors follow this backwards procedure when it comes to making investment decisions?

Like many other money missteps, my first inclination is to look back into the flawed history of the client/advisor relationship. The backbone of this relationship has always carried a “what have you done for me lately?” vibe, slowly evolving from stock picking, to mutual fund picking, to asset allocating, to the Frankenstein’s monster consisting of all the above. With this at the core, the measuring stick for success rests solely in the performance section of investment statements. This is how the risk-adverse Grandma winds up with all her money in tech stocks. The door opens to habitual tinkering, market timing, trend chasing and overtrading. Who does this benefit? Shocker: not the investor.

The Similarities Between Travel and Financial Planning

The solution to correcting this mistake could be to reframe how we approach the subject. I’ve always enjoyed the similarities between travel and financial planning. Objectives, goals, timeframes and budgets are interchangeable phrases in both practices. Despite having much in common, we are quite good at one and not so great at the other2. What if we applied our travel process to a slightly more important task?

Begin with the destination3 and work backwards. The destination then influences the travel dates (helpful tip: Try not to visit NYC in February as it is by this month that the winter has shattered our spirits and residents are no longer friendly) along with potential costs. Voilà, we are ready to select how we are going to get there.

What does this have to do with money? Simply put, investments serve as the vehicles to take us to our chosen destination. Just as a trip to the neighboring town would most certainly involve different vehicles than an excursion to a remote island across the globe, planning for an imminent down payment on a home requires different investments than a goal twenty years in the future, such as retirement.

Perhaps with a better understanding of the vehicles available, we may be less likely to hastily trade in our cars during the next traffic jam. Let’s focus on some of the different ways to get from Point A to Point B. Doing my best to avoid financial jargon, what follows are a few major asset classes and what I consider their comparative vehicle.


Vehicle: Bicycle

Every individual should learn how to use this vehicle before progressing to other options. Super-efficient if traveling a short distance but increasingly inefficient the further you need to go. Can be useful to decrease stress and blow off steam in times of heightened uncertainty. Requiring a continuous blend of stamina and strength, it’s by far the most physically demanding vehicle. Favored by those who value control (or the illusion of it) above all else. Long history of failing to keep pace with surrounding vehicles. Proven time and again to be riskier than believers are willing to accept (for additional perspective, see Cash is King?”) 4.


Vehicle: Airplane

Most efficient vehicle for long distance travel, not suitable for short. Ideal for individuals who function well without the need to be in control. Has the potential to be very expensive if not properly selected. Requires discipline and a strict following of rules to be successful, while cutting corners can bring about disastrous consequences. Prone to turbulence, unanticipated delays, abrupt cancellations and occasional bouts of sickness. Long history of success, but the failures will garner all the attention.


Vehicle: Train

Ideal for those willing to sacrifice some speed when traveling lengthier distances. If properly selected, different variations of this vehicle could also be relied upon for shorter trips. Has a sneaky characteristic of being more expensive than it appears to be. Favored by those who value predictability (or the illusion of it). Prone to delays and congestion, but still somewhat (NYC subway aside) dependable in times of environmental uncertainty. Must be comfortable placing trust in others, infrastructure and potentially governments.

Real Estate*

Vehicle: Recreational Vehicle (RV)

Has the capacity to travel both short and long distances, albeit with unique disadvantages for each. Its value is only truly known when it’s on the market to be bought or sold, rarely in between. Typically involves a steadily increasing cost for regular care and maintenance, regardless of age. Regularly purchased using one’s credit and the final amount spent for the vehicle comes to a multiple of the sticker price. Although they sacrifice time and speed on longer journeys, advocates are typically passionate and remarkably patient when faced with adversity. Favored by those who value the ability to see, touch and use the vehicle.

* This is not including a primary residence or professionally managed REITs. For the sake of this exercise, I am referring to personal rental properties, timeshares, vacation and second homes.

Hedge Funds

Vehicle: Yacht

Our first ‘luxury’ option of the bunch! More for prestige than utility, this vehicle not only looks great traveling long and short distances, but also when it’s immobile or traveling in the complete opposite direction. Some even have a rare ability to completely sink yet resurface with a new name and fresh coat of paint. In addition to an exorbitant sticker price, it comes with a very knowledgeable and highly compensated crew. Typically favored by those who value exclusivity above most else. In the past these could be considered great bang for the buck, but an influx of imitators, lower quality offshoots and the occasional criminal have clogged many of the pathways which made them so valuable.


Vehicle: Speedboat and/or Sports Car

Quite possibly the loudest individual vehicles available. Best suited for well-trained professionals and insiders, but accessible by the mainstream if willing to pay a premium. A fairly ridiculous choice as an individual’s only vehicle for all travels, however the potential to supercharge speed will consistently entice dreamers. You will rarely, if ever hear about the many letdowns, yet should be prepared to be bombarded and tempted by the much rarer tales of triumph.

Insurance Products**

Vehicle: Garbage Truck

I suppose this can be presented (or sold) to an individual as a defensive vehicle with the lure of a safer journey. Favored by those who are willing to pay an inflated price for protection (or the illusion of it). Extremely tough and expensive to redirect the minute it is put into motion. Has enough space to take you to your destination but is mostly filled with everybody else’s junk. Choosing this vehicle almost surely guarantees doing a greater service to others than yourself.

** This is in reference to the annuities and life insurance products sold as enhanced retirement vehicles. We generally favor low-cost term insurance for wage replacement or estate liquidity when warranted.


Vehicle: Hyperloop5

Currently more of an aspiration than an actual vehicle. Highly speculative mode of transport with loud and highly obsessive promoters. Promising technology still in its early stages, with a glut of makers vying for their vehicle to be the survivor accepted by the masses. Recently given an abbreviated test-run which produced unsettling results. Has not yet been tested for long journeys. Has the potential to blow past other options in terms of speed. Looking back into history, the last time a vehicle was recorded at a similar pace was in The Netherlands in 1637.

Take an inventory of what you own and ask yourself: “Are these the right mix of vehicles to take me to my destination?” Doing this now may help keep emotions in check the next time (when, not if) your vehicles seem to be going in the wrong direction. Roads have potholes, oceans have abnormal waves and even clear air can have turbulence. Surround yourself with a team of worthy advisors, plan your destination accordingly and trust the process thereafter. I’ll leave you with this quote from the late renowned financial planner, Anthony Bourdain.

“Travel isn’t always pretty. It isn’t always comfortable. Sometimes it hurts, it even breaks your heart. But that’s OK. The journey changes you; it should change you… You take something with you. Hopefully, you leave something good behind.”


  1. https://www.amazon.com/Mistakes-Every-Investor-Makes-Avoid/dp/1118929004
  2. https://www.fool.com/retirement/2017/06/04/americans-care-more-about-vacations-than-retiremen.aspx
  3. https://creativeplanning.com/blog/begin-with-the-end-in-mind/
  4. https://creativeplanning.com/blog/cash-is-king/
  5. https://en.wikipedia.org/wiki/Hyperloop

This commentary is provided for general information purposes only, should not be construed as investment, tax or legal advice, and does not constitute an attorney/client relationship. Past performance of any market results is no assurance of future performance. The information contained herein has been obtained from sources deemed reliable but is not guaranteed.


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