5 Best Mistakes I Ever Made

Tonight is Yom Kippur – a Jewish holiday that invites us to atone for our sins and clean up our act.  Of course there is a big difference between a sin and a mistake but they sometimes hangout in the same neighborhood. It’s true that “sins” are usually devastating.  But mistakes rarely are.  In fact, sometimes our errors are the best things that happen to us.  At least that’s been my experience.   That’s why I decided to republish this today.  See if this resonates with you.

Do you lament the mistakes you’ve made in the past? I know I do.   For example…why did I start playing drums when I was 11? Do you know how hard they are to schlep around? What – a guitar wasn’t good enough?

All kidding aside, there are things we all regret. But it occurred to me that a vast majority of the “mistakes” I made over the years turned out to be the most important and helpful turning points of my life. If you think about it you’ll see the same might be true for you too.

Here’s a list of the 5 biggest “mistakes” I made and how they helped me:

1. I got married too quickly.

My wife and I knew each other for a very short time before we got married. We were both young and didn’t even understand what being married meant. (27 years later, we’re still learning.)

Shortly before the ceremony, I asked myself if I really knew what I was getting into and I didn’t lie to myself.  The truth was that I didn’t know the first thing about what I was getting into. We had never even talked about money.  As a result, I had some real fear that I was making a mistake. I didn’t have doubts about my wife, but I didn’t know if I was ready or not. After all, I had no experience with making a lifetime commitment.

Even though I didn’t know what I was doing, I got married. Was I just really lucky that it worked out? (Luckier than my wife was…I can tell you that.) Yes…but it wasn’t just luck. We were deeply in love and it felt right to be together and to start building a life.

I played the odds. Since my wife was such an amazing person, I concluded that if I wasn’t ready at that point, I’d never be ready. I went for it. Fortunately, so did she.

2. I started my business before I was “ready.”

I am a serious “Type A” personality and a control freak.  I like to have all my ducks in a row. I started thinking about starting something of my own for two years before I did it. I was in serious planning stages for a year before I took the plunge. I kept telling myself that I wasn’t ready, but my wife finally convinced me to just do it…so I did.

The result?

I learned as I went. I encountered unforeseen bumps in the business world but navigated them and survived. I had many sleepless nights. I had to work really hard. But the business succeeded.  Had I waited until I was fully ready, I never would have done it. There is no “you are ready” bell that rings when it’s time. That’s why they call it being an entrepreneur. You take risks.

I had a good client base, I knew what I was doing and I had a good sense that we’d make it. In the end, the business turned out to be much better than I’d ever imagined. But I’d be lying if I didn’t admit how frightened I was at the start.

3. I had kids before I could afford them.

After my first child was born, somebody asked me what I was waiting for before having more. At the time, I was living overseas working two jobs and couldn’t afford diapers. My bride worked but was interested in becoming a stay-at-home mom. She wanted more children, but I wanted to wait until I had a stronger financial footing. A friend suggested I should I have a little more faith.

My wife and I discussed this and decided to continue building our family. We never discussed the financial aspect of having children again and had two more lovely daughters. Our children are our bounty in life. Our most precious blessing. My fear almost got in the way of that.

4. I wrote my first book.

By 2000, I had been in the business for more than 15 years and I was really sick and tired of the “conventional wisdom” from Wall Street. The wisdom seemed very much centered on helping Wall Street rather than Joe Investor. I wanted to write about that and alternative investment strategies that try to help investors safeguard their assets, but there were three problems:

a. I didn’t know how to write that well.
b. I didn’t know anything about writing a book.
c. I didn’t have that much spare time because I was putting everything I had into growing my business.

What happened?

A buddy of mine had just finished writing his book. With all due respect, it wasn’t that great. But I figured if he could do it, so could I. In the end, it wasn’t a bestseller but I was (and am still) proud of what I did. It took two and a half years to write and I went about it all wrong…but I got it done and I accomplished something that was important.

I ended up just trying to do the best I could with the time and money constraints I had. In the end, it didn’t matter what anyone thought about it…I was happy knowing I did the best job I could.

5. Started Wealth Pilgrim.

I started Wealth Pilgrim because I was told it would be a good way to connect with people and build an audience, some of whom might buy my book later on. (Rather selfish now that I think about it.)

I wanted to communicate the idea that you can improve your financial situation, you can learn to accept financial realities you can’t change and either way, you can have a great life. So I was clear on the message but didn’t know how to get it across.  I didn’t know anything about blogging. I was afraid and kept putting it off. I don’t know what finally pushed me over the edge, but I ultimately took the plunge.

The blog has become something entirely different than what I expected. It’s become a great little small business idea on its own. I’m seeing a community sprout and I love being part of it. People chime in with ideas I never thought of. I learn so much everyday and it’s crazy fun. I never anticipated learning so much.

Ultimately, I have no idea what my blog will become but I’m enjoying the ride one day at a time. I’m really glad I did it.

This is a really long-winded way of suggesting that if there is something you’re considering doing but still on the fence about, maybe it’s time for you to go for it. It will probably have unbelievable benefits, although you may not imagine what they are now.

There are always plenty of reasons to stay put and not try anything new. Change is dangerous and usually hard work.

Bottom line?

Think it through. Get council. But at the end of the day, you can’t predict the future. Any important decision you make has risk, and you’ll have to take action without having complete knowledge of what lies in store. Do it anyway. You will never be completely “ready” for anything important. Don’t let that stop you.

Have you found that the decisions you feared most had the best consequences? Are you putting something off because of your fear?