Know Your Retirement Options

As an entrepreneur, you plan each day. What’s your plan when you sell?

You probably love what you do. Most of us in this industry are dysfunctional enough to still get a kick out of winning jobs, nurturing great employees, creating lasting relationships, and making our competition squirm. If we live long enough, we see good and bad economic times, years of big profits, breakeven, and alas, losses.

Your legacy

There is something inherently attractive about branding that impacts our psyche; it can provide an allure of seeing our work live on in the public eye. Whether you call it a legacy or short-term immortality, having your creative juices coalesce into a building sign, vehicle wrap, or interstate electronic message display is meaningful.

From a psychotherapeutic perspective, the psyche is the part of us that is the most influential in effecting behavioral change and improving self-esteem. When you envision and execute a great design that works, it is very satisfying. That means it feels good.

Another legacy you can leave is the enterprise you have spent years perfecting. You might be lucky and have a child that wants to dance in your shoes when you are finally done working those long and sometimes lonely hours.

I’m not a big fan of just gifting a hard-earned business over to your offspring. They need skin in the game so have them buy it if they have a dream like you did. You either had to create this endeavor originally or buy it yourself. There is no free lunch, even if you are mom or dad. Sorry, I am from the Baby Boomer generation.

Retirement planning

You probably have not spent a long-time planning for retirement and assumed that when you sell the company, that’s your retirement plan. This is common for us over-achieving, tunnel-visioned, persistent
entrepreneurs with obsessive-compulsive disorder.

While we can multi-task when required, we are best at time-sensitive project management to its conclusion. That often leads us to let slip the important aspects of our personal life — and finances, especially planning for retirement.

As I’ve mentioned in previous articles, you should always make any large financial decision, whether capital equipment investment, expansion, or hiring with its impact on the day you sell your business. That gives you a different strategy and way of looking at decisions. In fact, it will sometimes lead to forgoing a decision when you weigh the alternatives. When you are focused on the outcome (selling the business) your brain considers alternatives in a new light.

Get legal advice

Consider hiring a business attorney before you sell. A legal professional can perform due diligence, oversee disputes, negotiate on your behalf, provide clarity and confidence in the myriad of contracts and agreements, and minimize the chances of a legal dispute.

You will need a valuation of your company’s assets to determine your selling price or range. What you think the business is worth is not always what the numbers prove. Assets, revenue, and profitability all play a part in an accurate valuation.

Finding a buyer

Finding a buyer has many routes. Your vendors can often help you locate a firm that is interested in acquisitions. The business attorney you hire may have a path to help you sell or advertise. There are broker firms that specialize in buying/selling businesses for a fee.

Congratulations if you can achieve an asset sale of your company for millions of dollars and have no debt at closing. You may only need a great financial consultant to help you keep from having inflation and/or taxes erode your big chunk of money so your funds last the rest of your life.

Transition steps

You may have a payout plan as part of your closing that lasts a year or longer which may help with income taxes (and they will be heartbreaking.) You may even be asked to stay on and work for the new entity for a minimum term with an Employment Contract to help the transition and ease you into the next phase of your life (depending on your age.)

Most definitely, you and the new owner will execute a Non-Compete Contract that is negotiated for its term, stipulations, and geographical conditions. I would urge you, however, to start right now thinking about this future event.

Prepare for the end

Make sure you have a current will. Again, invest in an attorney; this is not the time to download a will template from willsrus.com. Your estate and the sale of a business are complex matters that can have a big impact on you, your heirs, and those who seek your money (like the state and federal government). Out of the woodwork will also come other relatives you may not remember or recognize.

Retirement plan for the self-employed

What is the best retirement plan for the self-employed? It depends on how many people are in your organization.

    • A Roth IRA can be ideal if you have or do not have people working for you. The Roth IRA has limits on income generated and certain caps for wealthy individuals.
    • Solo 401(k): For individuals, especially business owners with no employees.
    • Simplified Employee Pension (SEP) IRA: Great for entrepreneurs with employees.
    • Savings Incentive Match Plan for Employees (SIMPLE) IRA: Also great for owners with employees.
    • Individual 401(k): Very common and excellent for entrepreneurs with employees.

Get help from a financial advisor

Choosing the right plan that works best for your situation requires thoughtful planning and collaboration with a qualified financial advisor. Consider a fiduciary planner; they only act in your best interest. Many do not earn commissions, so you will get objective advice.

When should you begin your Social Security benefits? While you can start at age 62, your monthly benefit rises 8% for each year you wait, until age 70, when increases stop. There are many factors to consider: your need for income, your other sources of income, and even your health. Your retirement planner can help you run the numbers and compare scenarios to decide whether earlier or later is right for your situation.

Health care is one of the biggest expenses most people will face in retirement. A 65-year-old couple today will spend an average of $315,000 on health care, according to a new estimate by Fidelity Investments. That’s scary. So, you need your financial professional to help you budget for health care needs as part of your retirement plan.

Speaking of scary, a 2021 study* concluded that running out of money in retirement scares most people more than dying. The concern is real, as longer lifespans can mean a retirement that lasts 30 years or more. Your lifestyle, when and where you want to retire all play a role and make your financial planner even more critical to working through these questions.

Dream for the future

If you are like most people, you want to have enough money to live comfortably through retirement, but also leave something behind for the people you love and the causes you care about. This is all part of estate and legacy planning and your will, durable Power of Attorney, living will, and living trust are aspects of strategy.

I want my surviving spouse to be cared for, but my overwhelming wish is to die broke. Again, I’m a Baby Boomer, and there were no inheritances available from relatives that have preceded me. As an entrepreneur, I missed a lot of family time, took short vacations, and did not make extravagant purchases. I will look forward to more time with kids and grandkids, golf, working out, bucket list travel, home projects, writing and being spontaneous!


When you are retired, should you still invest your money? It makes sense to reduce your stock market exposure as you move into retirement, but you should still have a diversified portfolio. As a successful entrepreneur, being diversified was part of your strategic planning. Therefore, it is still important to maintain a wide range of investments as the economy and markets rise and fall.

While your risk tolerance may have changed, do not let inflation rob you of the dollars you have accumulated. There is still time to grow your savings as you age. If leaving a legacy to your family or your church, or some institution motivates you, plan for it.

Start planning

If you are not quite ready to sell your business and/or retire, start your retirement plan as soon as possible. The older you get, the faster time seems to increase exponentially. Clock time does not really change, but mind time and how we perceive time as we age makes time fly by.

The processing power of your brain as you age slows. We are unable to process as many mental images per second as we could when we were children. Think of it as timelapse photography. The more photos that are captured per second (mental images we can process per second), the slower it seems time is moving. However, take fewer photographs per second (processing fewer mental images per second), and it will give the illusion that time is moving quicker. Simple, right?

Time does seem to move a lot quicker as you get older, so make the most of every second now.

Create a plan. Hire subject matter experts to help you with retirement and selling your business. Work on the plan, evaluate, and change as needed. Are these not the same things you do every day now? Do them now and live your later years as you deserve and are entitled to with good health and prosperity.

*Reclaiming the Future white paper referenced in the article What Happens if I Really Do Run Out of Money in Retirement? Retrieved and updated on July 19, 2022, from newretirement.com and allianzlife.com

Paul Ingle

Paul Ingle

Design Center Signs

Paul Ingle started selling signs in 1985 and has worked with regional, national, and international accounts with custom, architectural and production manufacturing firms. He has held various positions in sales, sales management, and marketing since 1973. From 2006 to 2017, he and his wife Nita owned Design Center Signs in Tyler, Texas (A Comet Signs Company.) Comet Signs is now part of Stratus, the leading facilities and branding implementation firm. Paul is a past president of the Texas Sign Association and its regional chapter the Greater DFW Sign Association. Contact him at paul.ingle@cometsigns.com.

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