I love working with the tech community. I started my career at Microsoft and have since been inspired by the creative and innovative minds of folks working at tech companies large and small. I also enjoy working with tech employees, because as a personal finance nerd, I get to help people navigate the plethora of benefits available that are often only available at tech companies. Between RSUs, ESPP, Non-Qualified or Incentive Stock Options, Mega Backdoor Roth 401(k)s, Deferred Compensation, Legal Services, and even Pet Insurance, it is the benefits equivalent of picking from a menu of a Michelin three-star-rated restaurant.

Through my own experience as a tech employee and my experiences now as an advisor working with tech professionals, I’ve identified some of the biggest financial planning mistakes that can hold the tech community back from achieving financial independence and success.

Mistake #1 – Not Optimizing Benefits

We all are familiar with the paradox of choice. Most people, when faced with a long list of complicated benefits that even some financial professionals struggle to understand, will focus on the areas that are familiar and disregard the rest. Who wants to spend their free time reading about ESPP taxation or the mechanics of Roth Conversions on after-tax 401(k) contributions? Chances are that if you work for a growing tech company, you have very little free time to begin with.

While it may not be the most enjoyable use of your evenings or weekends, I can’t emphasize enough how valuable it is to invest the time to learn how to optimize your benefits now. Choosing to invest additional savings in your Mega Backdoor Roth 401(k) over a taxable brokerage account may shave a couple of years off your retirement date. Maximizing HSA contributions and investing the growing account balance can provide for a substantial amount of money to pay for high healthcare costs if you retire before you are Medicare eligible (age 65). Making strategic Roth Conversions during lower income years, such as in early retirement or during breaks from paid employment, can save hundreds of thousands of dollars in future taxes over the course of your lifetime. The list goes on, trust me.

If I don’t exercise for a week, or even a month, I probably won’t notice a significant difference in my overall health. If I keep telling myself that I’ll start a workout routine, but years go by without investing my time and energy into making the plan a reality, my physical fitness will take a toll, and I will also lose out on all the amazing benefits that exercising regularly provides. I may look back with regret at some point later in life that maybe certain health issues could have been minimized or prevented if I had spent the time to prioritize what is truly important. It is critical to think beyond how something may impact us in the short term and recognize the long-term impacts of choosing to continue to put something on the back burner. Ask yourself, what impact will this have on my life if I wait a year to prioritize my personal finances? What effect will it have on my life if I wait ten years to prioritize my personal finances? Chances are that impact is even greater than you think.

Mistake #2 – Building and Maintaining Concentrated Stock Positions

I consider a concentrated position to be any investment that comprises over a quarter of your investable assets. It can be easy to accumulate a concentrated stock position in the same company that is responsible for your paycheck. If you receive stock as part of your compensation, without a disciplined plan to sell shares on an ongoing basis, you will continue to accumulate more and more company stock. Over the past several years, countless families have become wealthy because of the stock compensation they’ve received and its seemingly never-ending climb in price. While the strategy of holding onto RSUs and ESPP over the recent past has worked out incredibly well, we know that continuing to maintain a concentrated stock position is incredibly risky if you want to ensure you maintain your newly built wealth.

There are two explanations for not reducing a concentrated position that I hear most often: (1) My company has outperformed the rest of the market several years in a row. If I believe in my company and our growth prospects for the future, why would I sell? (2) If I sell my company stock now, I’ll have to pay a significant amount of tax on the gain. Let’s debunk each of these as reasons not to diversify:

(1) Typically, returns of a single stock position are intensely more volatile than the returns of a market index. This can work out in your favor, or it can work to your detriment. Historically, about 12% of stocks result in a 100% loss.[1] In addition, approximately 40% of stocks end up with negative lifetime returns, and the median stock underperformed the market by greater than 50%.¹ This means that a few star performers drive the positive average returns of the market. The odds of randomly picking one of these extreme winners is 1 in 15.¹ If you’ve been lucky enough to hold one of these outperformers, I encourage some humility around acknowledging that maybe being in the right place at the right time has attributed to your rapid accumulation of wealth.

Companies that achieve such success and become the largest company in their sector may become subject to what is called the winner’s curse. Since the 1970s, data shows that sector leaders underperform their sector by 30% in the five years after becoming the largest company in that sector.¹ Over a long time horizon, you are probably more likely to obtain positive investment returns by ensuring you hold the future Microsofts and Amazons of the world through broad diversification, not concentration.

(2) I hate to tell you this, but unless you hold onto an investment until you die, you will have to pay tax on the growth at some point. I encourage people to think of paying long-term capital gains taxes as a good thing, because it means your investments went up and you made money. A surprisingly small fluctuation in stock price can wipe out any benefit of delaying the recognition of capital gains tax. As advisors like to say, “Don’t let the tax tail wag the dog.”

Mistake #3 – Burning Out

There has been a significant decline in Americans’ use of vacation time. Twenty years ago, the average American took almost three weeks of vacation per year. As of 2016, Americans average only about 16 days of vacation per year, almost a full week less. You might think that improvements in technology over this 20-year timeframe would allow us to be more productive and therefore take more time off. It seems that the curse of this increased productivity is a greater reluctance to disconnect from work and give ourselves the permission to unplug.

Taking more time off has a positive impact on your physical and mental wellbeing. For those that need more convincing to submit a PTO request, research has found that those who take vacations are more likely to get promoted than those who underutilize their available time off. Taking steps to prevent burnout can not only lengthen your career and make it more sustainable, but it can also get you an increase in title and a pay increase. If that isn’t a compelling argument for taking a vacation, then I don’t know what is. At Merriman, we want to help you achieve your definition of living fully, whether to you that means taking time off for an epic adventure or maybe you have a larger goal of making work optional.

Mistake #4 – Poor Risk Management

Here are some fun facts for your next socially distant dinner party. If you are a 40-year-old male and you were in a room with one hundred other 40-year-old men, statistically speaking, two of those men will pass away before they reach their 50th birthdays. Another seven will have passed away before they reach their 60th birthdays, and another thirteen won’t make it to their 70th birthday. Close to a quarter of forty-year-old men will die before age 70. Do I have your attention now?

I don’t bring these grim statistics up to scare you. I bring them up because I’ve seen first-hand how a failure to plan for risk and the realities of life can cause significant financial harm during an already emotionally devastating time. Nobody enjoys talking about death and disability, but it is a fact of life that we will all pass on at some point. It is only fair to the people we love that we at least protect them financially.

Estate Planning and Insurance Planning are often the two most overlooked areas in a financial plan for folks that have not worked with an advisor. Financial advisors will also tell you this is often where we see our clients procrastinate the most. There are many things in life that feel urgent but are not actually important. We put off the important items, like drafting an Estate Plan, to answer our emails and do other tasks that have more of an immediate pull on our time and energy. There will always be those items to complete that feel pressing, but try to think through the consequences of not completing your will or obtaining life insurance if, in fact, your time has actually run out.

Mistake #5 – Not Hiring an Advisor

Yes, I get it. Hiring an advisor means paying fees. And hiring a bad advisor can be more harmful than helpful. But just like everything else in life, there can be a lot of value in employing the knowledge and resources of an expert. I don’t cut my own hair for a reason, and I wouldn’t dream of providing my own defense in any sort of lawsuit. If you have a handle on your investments, are rebalancing your portfolio like a pro, and have done extensive research on your company’s benefits and how to utilize them, then by all means, carry on, you fellow financial-planning nerd. I wish everyone fell into this category, but it is rare that I talk with someone who doesn’t need help in at least one major financial planning area.

If you do hire someone, be sure to hire a fee-only fiduciary advisor. You’ll need to explicitly ask this question, and if the answer is no, I suggest you run far, far away. Also, if you’re afraid of commitment, ask what the process and cost is of leaving an advisor if you aren’t seeing value from the relationship. Work with an advisory firm who isn’t going to make it difficult or expensive to end your relationship. Without any significant barriers to exiting the relationship, your advisor will be motivated to make sure you are getting great service and will want to remain a client for years to come. If you’re looking for an advisor you’re compatible with, consider perusing our advisor bios. If you’d like to discuss your situation, don’t hesitate to contact me.

¹ Avoid Gambler’s Ruin: Bridging Concentrated Stock and Diversification

Disclosure: The material is presented solely for information purposes and has been gathered from sources believed to be reliable, however Merriman cannot guarantee the accuracy or completeness of such information, and certain information presented here may have been condensed or summarized from its original source. Merriman does not provide tax, legal or accounting advice, and nothing contained in these materials should be relied upon as such.