What advice would you give the younger you?

by jeffhilimire on March 9, 2012

Yesterday I went to lunch with some of my Engauge colleagues and I was asked the question, “What advice would you give the 27 year old you?” It’s probably one of, if not the, best questions I’ve ever been asked in these sessions.

So, what advice would I give my younger self? Other than “invest in Apple” which one of the guys jokingly suggested. While I didn’t exactly answer this well during the lunch, I made a note to spend some more time thinking about it. Here’s what I came up with (by the way, this is me talking to myself ;)

- Get out of your personal office and sit with the rest of the company. Soon after I was 27 we moved into new office space. I would have made sure there were very, very few offices and much more open space.

- Hire A+ people, and only A+ people. When I was 27 my company, Spunlogic, was really starting to grow. And we hired a lot of people very fast, many of which didn’t work out because they weren’t the right type of person to be successful in our company and culture. They were all talented and all had great resumes. But I no longer hire with those two aspects being the lead factor. Took me a while to figure that out.

- Keep playing tennis. Today I don’t, and I spent ten years of my life focused intently on that sport, seems a shame to hang up the rackets. But I did, and I regret it. Younger me, keep playing!

- Focus more. I definitely had (and still have) a tendency to spread myself thin and feel like I’m doing an “ok” job in many areas instead of a great job in one or two areas. It’s advice I’m giving myself right now, actually.

- Travel more with your wife. We have a lot* of kids now and traveling is very tough, plus we generally like hanging out with our kids and would rather spend time with them. But when we were younger we should have traveled more. Now its the, “when we’re 50 we’re going to travel all over the place!”, which is certainly something to look forward to.

- Start blogging. I didn’t start blogging until 2008. As soon as blogging was created (a long time ago), I should have started. I love it so.

- Don’t hate on Macs. Yep, I used to be the classic PC guy, making fun of Mac users without even trying them. Now, not so much.

- Be more patient.

- Mentor more. And be mentored more.

- Don’t take things so seriously. I have a tendency to do that. Definitely did it more back then.

What advice would you give your younger self?

PS – this post reminded me of a past one, 10 mistakes I’ve made so you won’t have to. There are some similar themes here though the timeframe of “when I was 27″ changes the context.

* Anything over 1 is a lot of kids, for those that don’t have them ;)

  • Joe Koufman

    I thought you were going to say that you would tell your 27 year old
    self not to engage with that Thai prostitute during the bender in Buenos
    Aires, but I guess you decided to leave that one out…  some things are better left unsaid.

  • Sargentpest

    I’m learning to mentor more, and be mentored more right now.  I think that is very important wherever you are in life.

  • Raghu Kakarala

    you forgot about telling your 27 year old self to buy a convertible… seriously there is a tiny window to own one and be cool, then you cant own one since its not “practical”, then eventually you own own but your balding and look like an idiot… just saying

  • Nicola Smith

    Some of the best lessons I have learned are around letting go of the things you cannot control or you will drive yourself crazy.  I also agree with Raghu on the convertible thing, the same rule applies to motorcycles :-)

  • http://www.mostlymuppet.com/ Seth Miller

    At 27 I’d just become a father for the first time AND I was starting a new job. I think I’d go back and tell myself not to waste so much time – that all those moments I wasted could add up to something great. Now, I wonder why I don’t have any time & I’m constantly dreaming of all the things I could be doing.

    That said, I think I’d have used my blogging for more than I did. At the time, I’d been blogging since 2002 and I wasn’t making the most of it. I’d have started a podcast & a very specific kind of fans site & maybe left my job. Seriously.

    No regrets, but I’d tell my 27-year-old self that the gulf between my dreams & reality was (is!) actually VERY SMALL. You just have to take those risks. 

  • http://www.concepthubinc.com Sherry Heyl

    I would tell my younger me – starting in Elementary School and all the way through to my first two years of running my own company is… take yourself more seriously. Follow your heart fast and furiously. Do not subscribe to other people’s egos and issues or carry any burden that is not yours to bear. 

  • http://twitter.com/TobyDiva Toby Bloomberg

    For me it would be the opposite of Sherry’s1st  thought. I would tell 27 year old Toby not to take herself too seriously, to believe in her skills and talents to the DNA of her core and not to hang around unhealthy relationships longer than necessary. 

  • http://www.jeffhilimire.com Jeff Hilimire

    Too bad there’s not a “dislike” feature on these comments ;)

  • http://www.jeffhilimire.com Jeff Hilimire

    This sounds like a “believe in yourself” mantra which I think would probably resonate with most people when they look back at their younger self.  Thanks for sharing SH!

  • http://www.concepthubinc.com Sherry Heyl

    There is a difference between believing in yourself, which I think I always have, and taking yourself seriously. I think the latter is a maturity thing for most people but also a lack of setting bigger goals. You can believe in yourself but choose not to set big goals – perhaps because “it just does not matter that much.” It does. 

    There is a fine line too when it comes to taking yourself too seriously. I have not even come close to that problem. 

  • Mara Maddox

    Rings very true.  I think the “focus more” is one of the hardest to achieve and don’t know that I’ll ever master it.  We could all use some help in that area!

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