My Tax Prof, Age 51, Reveals How We Can Get Lucky and Retire in Our Early 40s
It has nothing to do with striking the lottery
No one denies the element of luck at work and in life.
What about retirement? Or early retirement, for that matter?
My Tax Professor, Prof Andy, believes luck is critical to achieving an early Big R.
I think so, too.
But what exactly is it?
Can luck be broken into digestible nuggets of wisdom? Can it be replicated by others?
According to Prof Andy, that answer is yes.
“I Retired at 42. Not Many People Can Say That.”
It is a badge of honor Prof Andy wears proudly on his sleeve.
And he should.
Many people around me are struggling to retire in their 50s.
- Yes. Struggling is the norm.
- Achieving that Big R dream is the exception.
We met at the varsity eatery this afternoon. I was there to review a draft research paper with my economics professor. Prof Andy was preparing for the start of a term.
He waved to me when I stepped into the eatery.
I walked over.
We spoke at length. It has been 17 years since I graduated from Prof Andy’s tax planning class. I admitted to him that I lost it all.
He laughed many chuckles.
“Don’t worry. You are the reason I am still in business!”
We pivoted quickly. It went from our careers to our collective interest in 10 minutes.
That topic was,
- Retirement for me.
- Early retirement for him.
They are the same, and not quite.
“Prof Andy, tell me. At what age did you formally or informally retire?”
He appeared fit, agile and embraced his work with enthusiasm. I thought he retired (only) 2 or 3 years ago.
I was wrong.
He retired when he was 42.
That was 9 years ago.
The 3-Point Lucky Strike
Prof Andy is one of those lucky ones.
He doesn’t deny it.
According to him, the specialization of tax planning scored his first lucky break.
“Firstly, tax. I never wanted to be an accountant or a tax specialist. Come on. Who does? Everyone knows it is a boring profession. I didn’t know what I wanted to do at 23. I went along with it.”
I shared that sentiment.
Though I was enrolled in Accountancy school, it never crossed my mind to be an auditor or tax filing expert.
Never.
“I applied for jobs in investment and corporate banking. No news. Auditing is a no-no. So, I sent my CV to the tax team. They welcomed me with open arms.”
So far, no surprises.
But then, Prof Andy’s unplanned career in tax took an incredible uplift.
He was roped into the tax planning team (from corporate tax) because of high attrition. There, his career took off.
“My tax directors took me along wherever they went. It turns out that tax planning requires a specific business and money acumen very few have. I am lucky enough to have it.”
When talent is unearthed, luck compounds.
Prof Andy was rewarded with double promotions for 2 years in a row. Double-digit pay increment followed.
This is his advice.
“Want to be on the fast lane? Don’t do what you want to. Focus on what you are good at. Keep doing it. The money will come.”
Prof Andy hit director status in his 8th year of service.
Doors Opened One After the Other
“I was invited by the Dean of this school to come and teach. I grabbed the opportunity.”
I was surprised.
Isn’t teaching time-consuming? Prof Andy is a busy man, after all.
“The Dean was very sincere. He wanted real-life tax knowledge in the seminar rooms. I am free to deliver the course materials my way. I agreed.”
That, to Prof Andy, was another lucky strike.
He did not have to conform to rigorous and stringent standards. All he had to do was be himself.
“I was 38 years old then. I needed an alternative to 15-hour workdays. I said yes, and then figured things out later.”
I never had such experiences.
I would love to enjoy such career tailwinds.
That said, Prof Andy’s story isn’t over. He has a portfolio of investments beaming with luck, too.
The Big Tech Moonshot
I started getting annoyed with his never-ending string of great fortune 30 minutes into our conversation.
Please pardon me.
It is hard not to.
I rolled my eyes when Prof Andy babbled non-stop about his Big Tech winners.
- Apple trended upwards.
- Facebook (now Meta) shot up.
- Amazon reached stratospheric heights.
- Tesla, an opportunistic holding, delivered unprecedented returns in 2019.
Prof Andy’s portfolio swelled upwards.
When I asked what that portfolio net worth is — He evaded that question.
Instead, he said this.
“If you can figure out what is coming, you can ride that wave. I was lucky. I stared at my iPhone and saw the future. I cannot articulate why. I simply acted on it.”
Being greedy, I asked Prof Andy what his intuition says to invest next. He gave me a Joker’s grin.
And he said this.
“Tell me. What does your intuition tell you?”
Intuition?
I have no idea.
And maybe that is why the Lady Luck of Early Retirement hasn’t smiled at me… yet.
The Close
I know this article focuses on the idea of luck for early retirement.
That said, we can engineer luck into our Big R attempts by analyzing, taking apart what works for others, and pursuing those pieces of success that resonate.
There are 3 pieces of actionable items from the luckiest Prof I know.
They are,
- Developing highly specialized expertise that few people come with, and the world has an insatiable demand for it.
- Seizing the Plan B opportunity when it comes.
- Investing in our vision of the future world.
What else did I miss?
And perhaps the $1,000,000 early retirement question is this.
How many of the three do you currently have?
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This article is for informational purposes only. It should not be considered Financial or Legal Advice. Not all information will be accurate. Consult a financial professional before making any major financial decisions.