P.A.I.N.T. Your Financial Mountain

By Nicholas A. Harris CFP® 

Planning for retirement is just like climbing a mountain.

Wealth accumulation and reaching the summit are only half the battle. Wealth preservation and getting back down the mountain safely are equally as difficult.

The summer of 2021 afforded me the opportunity to climb three of Colorado’s “Fourteeners” (“14ers”) – mountains exceeding 14,000 feet in elevation. Standing atop the final summit of Longs Peak at 14,255 feet, elated at having just conquered one of Colorado’s most famous and difficult peaks, the parallels between mountain climbing and retirement planning struck me.

Each Fourteener demands physical exertion with varying levels of difficulty, from Huron Peak’s straight walk up on a clearly defined path, to La Plata’s scrambling “on all fours” at high elevations, to professionally guided rock climbing and rappelling on the North Face of Longs Peak. Despite their differences, like retirement planning, these climbs share five common sections, each with an associated obstacle.

Whether your end goal is conquering a mountain or ensuring financial security for your family, formulating an action plan will allow you to tackle the challenge with confidence.

Use the PAINT acronym below – Plan, Automate, Integrate, Navigate, and Transcend – as a roadmap to visualize your journey, overcome your obstacles, and guide you safely back down the mountain to solidify your legacy and success.


PROCRASTINATION (Ground Zero: 0 Feet to 9,500’)PLAN 

Climbing a mountain encompasses a plethora of risks, ranging from weather, to injuries, or even death. A climber minimizes these dangers by creating a checklist to cover every contingency.  

For a Fourteener, the checklist includes: water, food, layers of clothing, sun protection, proper footwear, and technology-aided route memorization. Packing the necessary items instills the confidence to begin the journey.

With retirement years or decades away, proactively planning might seem trivial or dull. Putting off important decisions is easy, especially around subjects where you may feel uncomfortable or not well-educated, like money, but you can make retirement planning fun!

Crack open your favorite wine with your spouse and create your own concise, two-or-three page Financial Planning Checklist, summarizing every area in your lives involving a dollar sign: Investment Objectives & Allocation, Retirement Plans, Cash Flow/Budget Analysis, Estate Planning, Insurance Planning, Income Tax Planning, Mortgages/Debt. Include subsections and bullet-points you can check off. Then, use it like a Fourteener checklist to catapult you into starting your safe and successful financial climb.


ACCLIMATION (Trailhead to Tree line: 9,500’ to 12,500’) AUTOMATE 

Fourteener hikes typically begin in the dark before you can see the top of the mountain. Nonetheless, you move forward, lungs acclimating to thinning oxygen levels. Your legs are working hard, but your mind is serene as adrenaline puts your body on cruise control.   

Just as your body goes into autopilot early in a Fourteener summit attempt, families should put two areas of their financial plans on automatic as early as possible in life:   

  1. Spending – create a family budget/cash flow analysis and spend less than you make every month. Income minus expenses equals discretionary monthly deficit, or surplus. Your goal each month should be to have a family surplus. This monthly surplus will allow you to create a cash emergency fund and allow you to begin saving more money into long-term investments like stocks.
  2. Saving – just like your mortgage, rent, or car payments are automatically deducted from your checking account each month, you should have money automatically deducted from each paycheck to go directly into your retirement plan (401k, 403b, SEP IRA, etc.) and be invested for the long-term in a well-diversified portfolio heavily weighted towards stocks/equities.  

Spending less money than you earn and making recurring monthly contributions in a retirement plan are easier said than done. Nevertheless, automating these two simple steps early will instill confidence and begin to propel your net worth upward by minimizing debt and compounding wealth. 

INCLINE (Tree line to Summit: 12,500’ to 14,000+’) INTEGRATION 

After hours of hiking, you get your first view of the mountain you are trying to conquer. The majestic sight of the summit far above combined with tiring legs and shortness of breath from thinning air is equal parts beautiful and humbling.  

At this point, you can turn around or keeping inching upward. The key for the last 2,000 feet of elevation gain is to take your time and be patient. Walking too fast or running up the mountain will quickly wear you out, or worse, cause you to slip and fall, the absolute last thing you want at 14,000 feet. 

The same is true of investing and planning for retirement. When your wealth is increasing, do not abandon the plan because of a market crisis du jour and do not overcomplicate your financial situation. Instead, remember these three important points:   

  1. Incremental differences in rates of return will go a long way in compounding your wealth:
    • The ending value of a $1,000,000 portfolio compounding at 5% annually over 30 years is $4,321,942. 
    • The ending value of a $1,000,000 portfolio compounding at 7% annually over 30 years is $7,612,255. 
    • Yes, a 2% difference in rate of return equates to a $3,000,000+ ending value difference over a 30-year period.
  2. It is advisable to have a fully diversified portfolio containing some cash, bonds, and other assets not highly correlated to the stock market, but let equities (i.e., shares in high quality companies) be the main primary growth driver of your family’s wealth.
  3. Integrate your wealth – consolidate and simplify your accounts at one financial institution so you can keep track of your overall portfolio allocation, risk, and rates of returns. Having 10 different accounts at 5 different financial firms does not make you wealthier or more diversified. Instead, it makes income tax preparation and estate administration for your heirs more cumbersome, can lead to costly errors (e.g. beneficiary designations not comporting), and makes it next to impossible to know the actual rate of return and level of diversification across your investments.  

Implementation and integration of an equity-centric, fully diversified portfolio strategy will allow compounding to work its magic gradually over time. Going successfully from the tree line at 12,000 feet to the summit at 14,000+ feet demands patience, a slow pace, and perseverance. Trust the strategy and do not abandon it. You will be rewarded at the top.    


NAIVETÉ (Descent: 14,000+’ to 9,500’)NAVIGATE 

The summit is just a halfway point. Getting to the top is optional. Getting down is mandatory.” – Ed Viesturs, high-altitude mountaineer

You reach the summit, snap pictures of the breathtaking views, and take a quick break. Then reality sets in. Despite your exhaustion, you need to get back down the mountain ahead of any storms. The descent is physically exhausting and painful. Your body screams at you to stop, but your strongest muscle, your mind, keeps you moving forward and downward.   

Just as descending a mountain is mandatory, death is certain. Do not be naïve or nonchalant about dying.   

If you love your family, are fortunate enough to earn a decent income and eventually build up your wealth, don’t overlook these two areas of financial planning:  

  1. Life insurance – primarily to help your spouse cover major expenses like a mortgage and college tuition if you pass away and your earned income disappears. Term insurance with a finite end-date at some point in the future (15 years, 20 years, 30 years) coinciding with a mortgage maturity date and/or your youngest child graduating from college is usually adequate and offers reasonable premiums.  
  2. Estate Planning – work with an experienced and reputable attorney to put in place Wills, Trusts (if applicable), Powers of Attorney, and Advanced Medical Directives. These days, estate planning is less about avoiding estate tax and more about ensuring your hard-earned money administratively flows down to your heirs as seamlessly as possible. 

While the descent is uncomfortably difficult and the pain in your legs and feet unavoidable, you are also inching closer to toasting the end of your safe and successful adventure.   

Insurance and estate planning are your aching, yet necessary, legs and feet. In the event of your death, they both allow your family to avoid falling off a financial cliff and enable your loved ones to keep moving forward financially. 


TIRED (Home Sweet Home: 9,500’ to 0’)TRANSCEND 

Now you have returned home safely, or, in this analogy, have made the decision to retire. What’s next?   

Don’t flunk retirement by viewing it as an ending point. You may miss the camaraderie and exhilaration of your job, but this is the time to celebrate and start spending a portion of the money you worked so hard to accumulate.  

Retirement is also a chance to reinvent yourself. Is there a deferred passion or another professional or educational interest you want to pursue? What hobbies or bucket list destinations call? Are there charities to which you want to give time or money? Are you spending enough time with family and friends?  

A Career and Life Transitions Coach can help if you are having trouble prioritizing what is important to you. They will help you focus on your values, what brings you happiness, and how to spend your time, talent, and treasure moving forward. 

Do not allow complacency and procrastination to derail your retirement. The safest route to the summit of financial freedom necessitates a plan to reach the top and a purposeful strategy to ensure a successful descent back down the mountain. You will be rewarded with peace of mind that your family is financially secure each step along the way.  


As seen in Virginia Business, December 2022.

Disclosures: Material presented is meant for general illustration and/or informational purposes and is not indicative of any specific investment product. 

Investing involves risk including the potential loss of principal. No investment strategy can guarantee a profit or protect against loss in periods of declining values. Past performance is no guarantee of future results. Please note that individual situations can vary. Therefore, the information presented here should only be relied upon when coordinated with individual professional advice. 


Contact Michelle Tigani

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