Lessons learned from 20 years in the business, Part 1

For the next several weeks, I’m going to look back at my career and espouse things I’ve learned. No, I’m not retiring; I’m not dying (which would be a subcategory of retiring). Rather my firm, Personal Money Planning, is celebrating its 20th year. I figure I must have learned something that could benefit someone. I’ll keep this up until I run out of thoughts or get tired of pontificating.

Today I’ll focus on a saying that I’ve come up with (or really, that I smashed together from other sayings): Hope for the best, prepare for the worst, and enjoy what actually happens.

As I’ve mentioned in the past, people like entrepreneurs, expectant parents, and fiancées all have marvelous dreams of what the future holds. Well, that might happen.  However, if you ask veteran business owners, empty-nesters, and those celebrating their golden anniversary how their dreams compared to the reality, you’re likely to hear more about some trials and tribulation than the ultimate dream.

Now, just because bad things might happen doesn’t mean you should give up before you start. It just means that you want to be a little realistic about your prospects. Sure, dream about what you are hoping your future will hold, but then ask yourself if the worst-case happens, what are you going to do?

When I first started the business, I worked with the Small Business Development Center. My counselor was Paul Cook. He and I went back and forth over a spreadsheet I developed to attempt to predict what finances would look like. I had one line that traced out what I thought was a reasonable expectation for growth. The other line was what I predicted the worst-case scenario might be.

Guess which one reality followed?

And that was before the 2002 recession and the more recent financial crisis. In fact the 2000-2002 bear market was pretty important to my firm’s current success. You see, after the bottom fell out of the tech market, folks just stopped coming into the office. They were scared. A year later, we had the 9-11 tragedy. That certainly didn’t help matters. And after all of that, the true recession hit in 2002. We had just started to “make it” when this triple-whammy hit. It wasn’t pretty.

But if we hadn’t gone through that, I would not have learned the lessons that got us through the 2007 – 2009 debacles pretty much unscathed.

That’s why the last bit of my little saying, “…and enjoy what actually happens” is perhaps the most important part. Maybe “enjoy” isn’t the right way to describe it. Perhaps, “appreciate”, “learn from”, and “be thankful for” are better descriptors of what you should do. The idea is to not get either too giddy or too sullen that you miss the lessons from the day-to-day experiences.

Hope for the best, for why else start the journey? Prepare for the worst, so that reality doesn’t end your endeavor. And, most importantly, in some form,  enjoy.