5 Regrets From My 20s

5 Regrets From My 20s

I’m pleased with how my life turned out, as I accomplished most of my goals relatively young. However, looking back, it didn’t have to be as tricky as it was in hindsight.

Do you ever think about the things you wish you had done differently when you were younger? I know I do. As someone who’s been around the block a few times, I’ve had my fair share of regrets, especially regarding my 20s. But you know what? That’s okay! Life is all about learning and growing, and the mistakes we make along the way are part of that journey.

In this blog post, I want to share five of my biggest regrets from my 20s. These are things that I wish I had done differently or something that I wish I had known back then. I’m sharing them with you, hoping they might help you avoid making the same mistakes I did.

1. Not Starting a Tech Business During the Dotcom Mania of the 1990s

As someone in my 50s, I have to admit that I feel a little twinge of regret when I think back to the dot-com mania of the 1990s. Looking back, I can see how many opportunities I missed by not starting a tech business back then.

I remember how exciting it was to see the internet changing the world and how everyone seemed to be discussing it. But at the time, my focus was on profiting from the strong uptrend in tech stocks, mainly driven by the speculation on the future value of the internet for business. I did well as an investor and trader; however, fortunes were made by early entrepreneurs in that sector and time. It was an opportunity of a lifetime.

Nowadays, when I see how successful some of those early tech startups have become, I can’t help but wonder what could have been. But I don’t dwell on it. Instead, I try to use my regret as motivation to keep pushing forward and exploring new opportunities for what is happening right now.

It’s never too late to pursue your dreams. So even though I may have missed out on the dotcom mania, I’m still excited for what the future holds with new emerging technologies and business models that can be created with them.

2. Not Creating a Website in the Late 1990s

I have thought about how different things might be if you started a website in the late 1990s instead of waiting until 2011. Even then, I was talked into it by my friend, who was big into websites. I’ve regretted not jumping on the website bandwagon at least 15 years earlier.

I remember when the internet started taking off, and websites were popping up left and right. It seemed like everyone was creating a website, and some of them were even making big bucks. But at the time, I was busy focusing more on the financial world and didn’t think much of it.

Now, when I see how much the internet has grown and how much money some people have made from their early websites after achieving dominance, I can’t help but wonder what could have been with mine if I had started much earlier. But I don’t beat myself up about it too much. After all, hindsight is always 20/20. I’m glad I eventually got my website going, which has become an enormous success.

Maybe I missed out on the website boom of the late 90s, but that doesn’t mean I can’t still get in on the action today or even decide to build something else later, like a more significant YouTube Channel. There are always new technologies and trends, and who knows what the next big thing will be?

3. I Didn’t Understand Risk Management in Trading and Investing in My Early 20s

As someone who has spent 30 years trading and investing, I can tell you that one of my biggest regrets is not understanding risk management when I was in my 20s.

Back then, I was young and eager to make significant returns. I didn’t fully understand the risks of trading and investing and traded too big, risked too many open profits, and didn’t have a good exit strategy to lock in years of outsized gains. I had a 50% drawdown from my equity peak in March 2000, which was a harsh lesson.

Looking back, I can see how vital risk management is regarding trading and investing. It’s not just about making money – it’s also about keeping what you make and protecting yourself from significant losses of open trade profits or giving back previous gains. And if I had understood that back then, I could have saved myself a lot of pain, stress, and financial loss.

But even though I regret not understanding risk management in my early 20s, I did very well in the 1990s, even after that drawdown. That decade set me up with enough capital to continue to trade seriously. I used it as a learning experience, and it did help me avoid significant losses in 2008 and 2020. I still apply those lessons to my current trading strategies through proper position sizing and using stop losses.

So if you’re starting trading and investing, take the time to learn about all the elements of risk management. It’s one of the most important things you can do to protect your capital and financial future.

4. Trading and Investing Too Aggressively When I Started

I can tell you that one of the biggest regrets I have is trading and investing too aggressively when I was in my 20s. My young ego was at the core of my holding too big of position sizes, holding losing positions for too long, not wanting to admit to being “wrong,” and launching into activity in the stock market before learning enough to know what I was doing at first.

Back then, I was young and ambitious, and I thought the key to making big money in the stock market was taking significant risks. So, I would make trades and investments without fully understanding the risks involved. Eventually, those last trades and investments didn’t pan out as I had hoped after the NASDAQ double-top in 2000 and the following bear market until 2002.

Looking back, I can see that I was playing with fire. Trading and investing are inherently risky, but you ask for trouble when you trade too aggressively. And the trouble is exactly what I got – I lost what was a lot of money to me at the time from my peak equity, which was a harsh lesson to learn. The same bullish aggressiveness that was the edge that helped me compound capital so well from 1992 to early 2000 was the same weakness that caused my losing streak and drawdowns. Ego strength in a bull market can be a weakness in a bear market when your strategy doesn’t adapt to new price action.

Now that I’m older and wiser, I can see how important it is to trade and invest humbly and with flexibility. It’s not about taking huge risks and being sure of your opinions – it’s about making intelligent decisions based on careful research and analysis, whether trading or investing. And if I had known that back then, I could have saved myself a lot of trouble.

The stock market did humble me a great deal, and I came back strong from 2003 to 2007 with a strong string of good return years and quickly returned to my previous equity peak early in the new bull market. This time I stayed humble and flexible and made good decisions based on probabilities and possibilities. I went into 2008 still modest, saving me from significant losses during that volatile bear market downtrend.

5. Marrying the Wrong Person

After starting with little when I was young and going through the ups and downs of life, I can tell you that one of my biggest regrets was marrying the wrong person in their 20s. Marrying the bad person can cost you financially, emotionally, and spiritually, setting you back from where you should have been.

It’s tough to imagine the pain and heartache of realizing that the person you’ve married isn’t right for you. And when you have children with that person, it makes the situation even more complicated.

I regret not being more careful about choosing a partner and not getting to know them before tying the knot. I regret not listening to my instincts and prominent warnings when I doubted the relationship.

But even though I regretted my decision 30 years ago, I can’t change the past. What I can do is focus on the present and the future. I should have prioritized my happiness, well-being, and children over staying in a bad marriage. You can learn from my mistakes and be more careful and thoughtful in future relationships. It’s much easier to avoid getting into a bad marriage than getting out of one.

Most importantly, remember that it’s never too late to start over and create a happy and fulfilling life regardless of where you are in your life journey. I returned from two divorces and am now happily married to a fantastic woman who makes me happy. Sometimes, the path to happiness is bumpy, but it’s always worth the trip. However, my life could have been much easier had I avoided two divorces.

Key Life Lessons

Life is like a roller coaster ride, full of ups and downs, twists and turns. Having regrets is natural, but it’s important not to dwell on them too much. Instead, use your regrets as lessons and stepping stones toward a better future. Don’t be afraid to take risks; research and manage them carefully. Choose your partners wisely, but if you find yourself with the wrong one, it’s never too late to start over if that marriage ends. Age is just a number; there’s always time to pursue your dreams and make your mark on the world. So keep pushing forward, stay positive, and never give up.