When Should I Retire

People pay me a lot of money for advice. It’s called consulting. Questions on taxes and money are what start the conversation. But once we get under the hood it becomes clear there is another motive. The real questions involve medical issues, raising children, starting a business and retirement.

It would be easy for me to give a short pat answer. It wouldn’t do much good, but I could do it. Instead, I ask a series of questions helping the client to come to her own conclusions. Some crazy tax guy from the backwoods of northeast Wisconsin will never have clever enough words to convey the right message. I have to help the client find there way there  on their own. If I say “Yes” to the best business idea ever and the client is not ready or in the right mindset, they will fail. 

And it always comes around to the finish line, aka, retirement. When can I retire? Should I retire? 

I could give you a simple formula if you want. Better yet, skip the whole post and scroll to the bottom for the quick and easy answer, for all the good it will do you. 

However, it might be better if I share a story and ask a few questions first.

 

Old Man Take a Look at My Life

I’m feeling old this tax season. At 56 years of age my eyes stray to the horizon. I’ve seen a lot over the years and this tax season is already one for the record books. 

I entered the profession full time in 1989. Since 1982, my senior year in high school, I have been stenciling in numbers on tax returns for side hustle money. I am at a total loss when I look back and realize I have nearly {gulp} 40 years into this career. There was no clue when I planted that first number on a 1040 for a quick twenty bucks how much it would dominate the remainder of my life.

After 40 years it might be time the cleats get hung up. There are entire communities dedicated to early retirement. I was nearly sucked in all the way 5 or so years ago when I met Mr. Money Mustache, a guy whose claim to fame is retiring at 30. The falling out is totally my fault. I found nothing familiar in the lifestyle presented so we had nothing to talk about. We came from different worlds.

So, if I’m going to help people reach retirement, shouldn’t I have a clue about my own? Well, I think I am more than qualified to help people attain and transition to retirement without ever planning on doing so myself. The best sports coaches are not always pulled from the greatest players of yesteryear. Sometimes, but not always.

If my retirement plans are a fantasy, why do I feel so old? Is it the clock and its incessant ticking? Do I think my skills are waning? All good questions. 

Tax professionals are a unique crowd. I belong to several Facebook groups dedicated to tax professionals only. The crowd is quite friendly until mid-February when things take a left turn. Normally quiet individuals start complaining about clients and their behaviors. Mid tax season changes by Congress and the IRS adds to the stress, and don’t think the folks with pocket protectors don’t let the rest of the crowd know about it.

To the best of my ability I do not complain about the tax code and especially clients. This tax season, only half over, has provided ample reasons for complaint. But it doesn’t help so I focus on what does; the things I can change.

You don’t live long in my profession before you notice strange things. Things most people never think about. 

You can’t imagine — unless you’re a tax professional — how many clients die every year.

It is rare for a tax season to pass where I don’t hear of a client that has lost a child. If not their child, a nephew or niece. I have at least two clients with a child that committed suicide. Clients that had a child drown, killed in an automobile accident and one that died playing a choking game. 

I prepared two decedent returns (a person’s final tax return) this year already. The first was for a 26 year old woman. I never know what to say to the client. The pain must be unbearable.

The second decedent return was picked up last night late. He was 38 when he died. 

In both cases medical issues were involved. They were sudden issues so no one had a chance to prepare or even say goodbye. The wounds are deep.

When should I retire? Reflect on your life and what matters to you. Do the things you most love. Never give those thing up.

Love Lost, Such a Cost

You can’t understand how much I love my work. This morning I was at the office at 4 a.m. Instead of knocking a few more tax returns out I decided to write and publish this post after a few months break due to medical issues in my family, still ongoing. 

With the exception of one tax return stalling me out, everything on my desk is fresh. I’m getting my work done and in a timely fashion so I had the luxury of writing for a few hours. Lucky me!  

I often get to the office early. It allows me more family time later in the day. I have the great fortune of satisfying both my great loves as a business owner.

But there is a cost for not retiring! Every time I walk in the door I take the chance the news of another dead client will reach me. So many of my clients from the early days of my practice have left this world.

A few weeks ago an elderly client came in with her son. She couldn’t get out of the van easily so we took her papers, prepared the return and brought her a copy of the return and signature pages to the parking for her to sign. She is 81 years old. She doesn’t need to file anymore, but worries so we file for her anyway.

We charged her $25. She has no money and was struggling to put food on the table. She asked for time to pay and we granted the offer. When Dawn, the preparer, brought this to my attention I told my assistant to delete her invoice. Dawn called to inform the client. The client cried. You see, people are good; all of them. They have pride. They are okay with a discount, but free makes them feel like they have taken advantage. It hurts no matter what you do. 

I am feeling very old.

A former employee is good friends with Dawn. The former employee visits a Feeding America food bank weekly to bring food to people shut in. Dawn asked for two packages. She delivered the food to the client. She cried again. 

I don’t know how long before the client will no longer need my services (dies). She has a son. Her husband died long ago. All I know is it makes me feel old.

 

Beyond the horizon of the place we lived when we were young
In a world of magnets and miracles
Our thoughts strayed constantly and without boundary
The ringing of the division bell had begun

 

When you practice as long  I have something else happens. I prepared taxes for young people back in the 1980s and 1990s. They got married, had children and sometimes retired themselves by now. Their children are now old enough to file a tax return and are having children of their own. Those children are starting to grow up. If I last much longer I will have filed tax returns for three generations in some families, if I haven’t already! 

And this is the part that hurts.

A husband and wife have been clients since about 1990. They worked with me many years ago when they and I had rentals. They were more than clients; they were friends. The husband’s health has deteriorated for years. He was admitted to hospice and was given less than six months. He is down to just over 100 pounds. It breaks my heart. The wife is suffering from dementia. 

Their daughter brought the news when I prepared (actually Dawn prepared) the return. A few days ago they had a fire at their home. It made the news. I don’t watch TV so I missed it. Dawn informed me the next day. I’ll never complain about bad luck ever again.

Ambition to reach the dreams of your life. Know what you are retiring from and retiring to.

When Should I Retire

The answer is different for everyone. There is no disgrace in wanting to keep doing what you do to fill your days. There is no disgrace in retiring, at any age.

I ask you these questions: What are you retiring from? And what are you retiring to? 

If your job is a drag it might be time to move on. Maybe a different job, one that fulfills you, or retirement. 

Before you take the long walk, consider this. Have you thought about an extended vacation or gap year? Do not confuse tired or exhausted with being ready for retirement. 

Maybe you are ready to retire, maybe not. 

For me, retirement is a hollow promise. The faces in my office are changing. Clients so familiar all these years are disappearing; first one-by-one, now in droves. With each passing minute I become the old guy with lots of crazy stories from history. 

I am desperately afraid of the night. This is what I do and what I am. I will not complain about complex tax law changes or clients sending me unreadable photos of their tax documents. I will gently nudge them in the right direction. They meant no offense and do not understand what it is like on my side of the desk. Age has granted me more patience; an example of a blessing from growing old.

Whatever path you choose, know you can always make additional changes in the future. You are not wedded to what you are doing now. Plans should be changed when things don’t work as planned. 

Most of all, do what you love. Life is too short for anything else.

 

We close with a few more words from Pink Floyd.

Encumbered forever by desire and ambition
There’s a hunger still unsatisfied
Our weary eyes still stray to the horizon
Though down this road we’ve been so many times

 

I have High Hopes for all of you.

 

More Wealth Building Resources

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Medi-Share is a low cost way to manage health care costs. As health insurance premiums continue to sky rocket, there is an alternative preserving the wealth of families all over America. Here is my review of Medi-Share and additional resources to bring health care under control in your household.

QuickBooks is a daily part of life in my office. Managing a business requires accurate books without wasting time. QuickBooks is an excellent tool for managing your business, rental properties, side hustle and personal finances.

cost segregation study can reduce taxes $100,000 for income property owners. Here is my review of how cost segregation studies work and how to get one yourself.

 

Keith Taxguy

14 Comments

  1. Jeremy on March 17, 2021 at 9:35 am

    Tired of lying in the sunshine, staying home to watch the rain
    You are young and life is long, and there is time to kill today
    And then one day you find ten years have got behind you
    No one told you when to run, you missed the starting gun

    Yep, it is definitely going to be a Floyd day today now.
    I need the continued perspective that life is short and carpe diem
    Appreciate your insight and thoughtful words as always.

    • Roger on March 18, 2021 at 11:43 pm

      Yeah you run and you to catch up with the sun but it’s sinking, racing around and come up behind you again. The sun is the same in a relative way, but you’re older. Shorter of breath and one day closer to death.

      It’s always a Floyd day in my house.

  2. Edward on March 17, 2021 at 10:08 am

    Keith, thank you again for a post of enlightenment. We have a great opportunity to dial things back (nice thing about tax consultancy), which will still enable us to keep the relationships as the most important part of the work. Happy filings.

  3. Sarah on March 17, 2021 at 1:58 pm

    Thank you Keith for humanizing the life experience in relationship to time and this agreed upon idea called money / taxes. We appreciate every ping in our inbox from your updates, and know that we couldn’t be who we are without all the gray hair experts caring for our well being – we thrive because of the efforts and dedication of humans like you. Hoping there is rest, play and FUN for you and your family throughout life.

  4. Mary on March 17, 2021 at 2:31 pm

    Wise words. Thank you. My Financial planner says I can retire in a few years. I desperately want to. But what I really want is probably a break. That extended vacation. or a Gap year. I know I cannot do nothing every day. So – I’m trying to think of a plan b. Maybe I’ll go work in the local Hallmark store. Or something completely different from corporate USA. I don’t know yet – but something to think about.

  5. Nanette on March 17, 2021 at 7:56 pm

    I so appreciate your perspective as I am your age and have been in this profession about the same time, and do not enjoy it so much anymore… it’s so difficult to know whether to hang it up. My Dad died unexpectedly on March 4 so trying to gather my wits for a run at tax season (as a solo practitioner)… overwhelming!

    • Keith Taxguy on March 18, 2021 at 8:25 am

      Nanette, I’ve had similar feelings over my career as well. As a solo practitioner you have options. This isn’t an all or none proposition for you like a traditional job might be. Cutting back is allowed. As an example: 15 years ago I ran a larger firm with 20 or more employees during tax season and thousands of clients. One day I decided to cut 400 of my least profitable clients. (Many were money losing clients when I looked deeper. They paid little while taking a lot of time with calls and questions and messy paperwork.) The next tax season was like heaven.

      With the formula in hand I cut my practice down to under 1,000 returns (just over 500 to be exact). Each client is now highly profitable and respects my time. I have a handful of employees because the returns I handle tend to be more involved. I love the pace and the work. Burnout has been disposed of. And I enjoy a very comfortable income. No need to tap retirement funds because I’m still adding to the pile and contributing to charity more than ever.

      Working on your own you can make nice side hustle money with maybe 100 returns, give or take, depending on the complexity of the returns. The nice thing about this profession is you can always add more clients later if you want to do more.

      I’m jumping to a conclusion, so forgive me. Considering the time in your career I am assuming {gulp} you have reduced debt (if any) and a nice nest egg set aside for retirement. If this is true you can take any path you want. If you love the work, keep doing it. Just not so much until you no longer enjoy it.

      I know. Easier said than done. Remember, we are a support team out here. Whatever path you choose we are with you. Out thoughts and prayers are with you and your family with the passing of your dad. You will find strength in all this.

  6. charlie @ doginvestor.com on March 18, 2021 at 8:48 am

    Why retire at all? I have family members in their 70s still working, some because they have to, but a few because they want to. You don’t need to work at a relentless pace of 40-80 hours a week. Perfectly acceptable to work 2x/week and do hobbies/family time/sail/golf the other 3 days or more.

    It’s a very interesting question, since I think if you can find something challenging, get paid for it, be financially independent, help others and it doesn’t have poor health side-effects from stress, then it’s probably better not to stop.

    I’m in a phase now where I’ve stopped corporate work, and am looking for my next stage.. go back to corporate despite the restrictions, start my own, or freelance. Sadly, my work wasn’t suited to doing contractual (private equity) so it doesn’t seem consulting/freelance is easy, unless I do some form of business consulting/management consulting.. anyway, trying to work it out! I know however that after my extended break of 2-3 years it’s time to start doing something again.

    Good luck on the tax season, and also hope that your daughter and family are coping with the difficult times health wise.

  7. Ashish on March 18, 2021 at 10:42 pm

    I really like ‘Do not confuse tired or exhausted with being ready for retirement’, I need a break as well!

    It is really kind of you to help people in need when you can be content with businesses and big clients. This was a touching article, I am participating in Toastmasters division contest this Sat. and my speech is related to children’s emotions as well. This is worrying trend!

    • Keith Taxguy on March 19, 2021 at 4:15 am

      You’re going to be great at Toastmasters this Saturday, Ashish. You are making a difference when you stand in front of the room and communicate a powerful message.

  8. Robin on March 20, 2021 at 1:53 pm

    Neil Young. Great songs, i’m singing in my head and writing

    “Old man, look at my life I’m a lot like you were, Old man, look at my life Twenty four and there’s so much more Live alone in a paradise That makes me think of two.
    Love lost, such a cost Give me things that don’t get lost, like a coin that won’t get tossed, Rolling home to you…”

  9. Todd on March 27, 2021 at 6:58 pm

    I appreciate your thoughtful posts, Keith. I have been reading your blog since the first post went up. I hope your family is doing well.

    As it turns out, this week I landed my first tax return client. I’m a CPA, but I don’t have much experience preparing returns (other than my own). Fortunately, he’s a friend with a very simple return – a good way for me to start.

    Any advice you can provide?

    • Keith Taxguy on March 27, 2021 at 9:09 pm

      Todd,

      Never stop learning. Also, focus your practice; you can’t be all things to all people.

      The toughest advice? You will make mistakes. You will not always interpret tax law the same as others. Don’t let an error or misjudgment get you down. It is part of the profession.

      And don’t take on too many clients. This field is littered with the carcasses of the burned out.

  10. Mark Mauhar on April 7, 2021 at 4:24 pm

    LOVE this post – very well said!

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