I don’t have regrets – everything that’s happened to me so far has led to a life that I wouldn’t trade – but if I had the chance, I’d probably like to say a few sentences to past versions of myself.
Dear 1988 Brent – Keep playing the piano no matter how boring it seems.
Dear 1990 Brent – Instead of drinking protein shakes to gain weight, enjoy your temporary skinniness.
Dear 1991 Brent – While your high school sweetheart is indeed drop dead gorgeous, brilliant, and kind, it’s completely okay that you are not the right fit for her, nor she for you.
Dear 1992 Brent – You’re making the right decisions by cutting high school classes and enjoying life.
Dear 1993 Brent – Cutting college classes, on the other hand, is a spectacularly bad idea, and you should finish college on your full scholarship even though you don’t quite understand what it’s good for.
Dear 1994 Brent – Don’t let a single month go by without a letter to your parents assuring them that you’re okay.
Dear 1995 Brent – Seriously, dude, do not trade in the Datsun 280ZX to buy a brand new Hyundai Accent on credit.
Dear 1996 Brent – Bankruptcy feels really shameful at the time, but it doesn’t determine your worth as a human being.
Dear 1997 Brent – As long as you’re broke, you should probably just move to Silicon Valley and gamble on getting a job in the dot-com boom.
Dear 1998 Brent – On your first day of a long French vacation, when you’re ordering food in a bar, don’t gamble on the steak tartare with the raw egg in the center.
Dear 1999 Brent – You’re a professional now, and professionals keep in written touch with inspiring people who have been influential in their career.
Dear 2000 Brent – Do not get drunk in the presence of the company receptionist because she likes you way more than she lets on, and eventually she just might marry you.
Dear 2001 Brent – At this point, you’re doing exactly the right thing by ignoring your dot-com buddies in California, because that ship has sailed.
Dear 2002 Brent – Get to know that Matt Mullenweg guy at the Houston Wireless meetings.
Dear 2003 Brent – When a company can’t pay your paycheck, you need to leave no matter how much you love your coworkers and your job.
Dear 2004 Brent – You’re doing a good job of going on wild spur-of-the-moment no-budget trips with Erika, but I bet you could go on even more, and you should, because you’ll never get these airline flight benefits again.
Dear 2005 Brent – Instead of being incredibly stressed at having one bad manager for a couple of months, realize that you were blessed to have years of great ones, and know that the next great one is right around the corner.
Dear 2006 Brent – Take more walks on South Beach.
Dear 2007 Brent – Seriously, if you didn’t want to walk on the beach, why the hell did you get an apartment that close to the water?
Dear 2008 Brent – Even though you’ve only been at that job for a couple of weeks, you did the right thing by quitting immediately with no safety net, because this would have killed your spirit for life, and a better one will come along literally tomorrow.
Dear 2009 Brent – Spend one hour per week listening – really, really listening – to each of your inspiring, insightful coworkers like Kevin Kline, Christian Hasker, Andy Grant, Billy Bosworth, Douglas Chrystall, and the rest of the gang of entrepreneurs at Quest.
Dear 2010 Brent – While it’s utterly terrifying to quit Quest, write a $20k check to pay back your MCM, and go out consulting, do not be even the least bit stressed about it because it’s one of the best things to ever happen to you.
Dear 2011 Brent – You can’t please everybody all of the time, so focus on making ten people happy – starting with your family and your business partners.
Dear 2012 Brent – Startups are a marathon, not a sprint, and you have to take even better care of yourself when training for the startup marathon.
Dear 2013 Brent – The ex-girlfriend who contacts you out of the blue is actually at death’s door, and you need to find out what you can do to help.
(Writing this was very rewarding. I started with a few years off the top of my head, then jogged my memory with my photo albums. Afterward, I found myself writing Now Brent a full letter as if I was looking back in the rear view mirror, and that was really rewarding too.)