10 Realizations of a Midlife Entrepreneur


by Guest Blogger, Lou Bortone

Did you ever have that nightmare- You know, the one where you’re getting ready to take your final exam, and you suddenly realize you haven’t been to class all semester? I still have that same dream, 25 years after graduating from Boston College! For me, I’m getting ready to take my Psychology final, knowing I’ve blown off most of the classes for the entire term. I’m totally screwed. Fortunately, I wake up and remember that I passed Psych by the skin of my teeth!

That recurring dream is simply my way of saying I still don’t know squat about Psychology, but I have definitely figured out a few things in the last few years of being a solo entrepreneur. As my penance for missing so many Psych classes, I’m happy to share my recent realizations, Freudian or otherwise:

1. Life will laugh at you as you continue to make the same mistakes, over and over again.

Silly human! When are you going to learn? If you’re going to make the same mistake, at least try to make the same mistake in a different way. Add some variety to your foibles and follies! There’s gotta be a lesson in there somewhere.

2. Plan big, but realize that life gets in the way.

A snow day and the kids are suddenly home from school. Your day turns upside-down. Or, you get food poisoning on the day of your big presentation. The car won’t start. The dog threw up on your shoes. Go ahead, make grand plans and set your daily goals. Just know that nothing ever goes exactly as planned and life will throw you curve balls when you least expect it. Go with the flow.

3. Please and thank you never go out of style.

When did you get so busy and stressed and grown up that you can’t remember your manners? Be nice. It’s not that hard.

4. It’s unlikely that you’ll get caught up on your emails.

You can fool yourself into thinking you’ll catch up, but why bother? I think mail carrier and Jerry’s nemesis Newman said it best on “Seinfeld,” when he said “The mail never stops. It just keeps coming and coming.” Of course, he was talking about the paper variety, but you get the idea.

5. Call your Mom.

Okay, I’ll admit it. My Facebook friends know way more about me than my own family. But that’s no excuse not to keep in touch the old-fashioned way. Call Mom via Skype if it makes you feel more Web 2.0.

6. Stop and smell the roses.

Unless you happen to live in New Hampshire and it’s the dead of winter and there are no roses to smell within a 500-mile radius. In which case, you probably need a vacation in a much warmer climate. I hear the roses in the Caymans are lovely this time of year.

7. Lighten up.

Why so serious? When my 11-year-old baseball star complains about losing a game or the state of the Boston Red Sox, I try to remind him that any day you’re not waking up in a third world or war-torn country is a pretty damn good day. (Then I tell him that I had to wait 40-some-odd years to see the Red Sox win a World Series! He’s already seen the Sox win it twice!)

8. Back up your hard drive. Seriously.

You really should only have to go through this experience the hard way once. (Refer back to Number 1, above.) Losing all your data is no fun and can be easily avoided.

9. Life is way too short to work with a-holes.

It really is. There are a lot of really cool people out there. Find them and hang out with them. Steer clear of those with a-hole tendencies.

10. Think Big. (I borrowed this one from my friend Michael Port, but it kinda just makes sense)

‘Nuff said.

About the Author:

Lou Bortone is a long-time marketing and branding consultant who helps entrepreneurs build breakthrough brands on the Internet, with services such as online video production, video branding, coaching and creative support. Lou is a former television executive who worked for E! Entertainment Television and later served as the Senior Vice President of Marketing & Advertising for Fox Family Worldwide, a division of Fox in Los Angeles. Lou is an author and ghostwriter of six business books, a Certified Guerrilla Marketing Coach and a Book Yourself Solid Certified Coach. Visit Lou’s website at http://www.OnlineVideoBranding.com and you can learn more about Lou’s Video Traffic Blast system at http://www.VideoTrafficBlast.com


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  • http://www.VivaVisibilityBlog.com NancyMarmolejo

    Lou, such wisdom! This is so beautiful and eloquent. I think you've got a web 2.0 version of Don't Sweat the Small Stuff on your hands!!

  • http://www.BruceElkin.com/ Bruce Elkin

    Great piece. Short, to the point, and light-hearted. Life is too short to over-think and take too seriously. But the important things are important.
    Thanks!

  • Lou Bortone

    Thanks, Bruce and Nancy! It was a fun, little exercise. I guess number 11 for me would be to try to stay out of my own way!Happy New Year!

  • http://www.VivaVisibilityBlog.com NancyMarmolejo

    I really like #9. My word for 2010 is "BOUNDARIES", and I truly believe that boundaries are a nice a-hole elimination strategy. Thanks Lou!! And you're a Mama's Boy, how I love that!!

  • http://www.melaniekissell.com melaniekissell

    I just watched "The Bucket List" last night, Lou, so #9 really resonates with me. At 56, I simply can't make room in my life or in my heart for "bummer buddies". For whatever number of years I'll be granted and graced with, I certainly don't want to spend them with "Negative Nellies"!Nancy, thanks for inviting Lou to be a guest blogger. Your invitation speaks volumes about your morals, standards, and values.

  • http://www.VivaVisibilityBlog.com NancyMarmolejo

    Thanks Melanie for appreciating us over here! "Bummer Buddies", that's a good one.

  • http://www.melaniekissell.com melaniekissell

    Glad that one tickled your funny bone, Nancy. :-)

  • http://www.VivaVisibilityBlog.com NancyMarmolejo

    Thanks Melanie for appreciating us over here! "Bummer Buddies", that's a good one.

  • http://www.melaniekissell.com melaniekissell

    Glad that one tickled your funny bone, Nancy. :-)