Lessons From Dumb and Dumber: Why Solopreneurs Need Their Own Harry...

As I sit here and reflect on my career and the current state of transitioning from the executive / corporate world to starting my own Fractional Marketing agency and consulting practice I notice my mind constantly drifts to all the uncertainty there is in the early stages of trying to build a predictable business with predictable income. Coming from the "illusion" of security from corporate life, it is still hard to shake that feeling that I just need to get another corporate job. I have lots of doubts... As experienced, knowledgeable and frankly just good at what I do as I am, I still question myself, my abilities, and in reality, my worthiness. Imposter syndrome is a real thing.

Oddly enough, as I was sitting here tonight thinking about my business I noticed I started to see a few different references and posts suddenly appear of the classic 1994 movie Dumb and Dumber on my social media feeds for some strange reason. I'm glad though because forgot how funny that movie was.

It started with this post from this linkedin post from Julia Nimchinski

Then it continued with a response to that post from Peter Wheeler that pointed to a Reddit Post.

And here is the said Reddit post that just sent me down the rabbit hole of one-liner quotes and describing scenes from the movie

Every "Lloyd" needs their "Harry"

As I proceeded down the rabbit hole of one liners and scenes from the movie I suddenly realized how relevant it is for entrepreneurs to always make sure you have your own personal "Harry" in your life being the voice of ureasonability, your cheerleader your friend to the end, your ride or die, that one special friend (or group of friends) that helps keep you going when business gets rough, and it will most definitely get tough. You will doubt yourself, you will get angry, you will get anxiety, you will get sad, you will get worried... I don't know where I would be if I did not have some Harry's in my life.

As a solopreneur transitioning from the structured world of employment to the wild frontier of entrepreneurship, you might think you need to go it alone. After all, isn't that what "solo" implies? But here's a plot twist for you: success often comes from surrounding yourself with the right people - your own personal "Harry", if you will.

Now, I'm not talking about professional mentors or industry experts (though they're valuable too). I'm referring to those friends who are just zany enough to believe in your craziest ideas. The ones who, when you say you're thinking of quitting your stable job to start a business selling artisanal sock puppets, respond with an enthusiastic "Why not?!" instead of a more reasonable "Are you out of your mind?"

These are your voices of unreasonability, and they're more crucial than you might think. Here's why:

They Keep You Dreaming Big

When the going gets tough (and it will), these friends remind you why you started this journey in the first place. They're the ones who'll listen to your wild ideas and, instead of poking holes in them, will help you inflate them even further. Remember when Lloyd exclaimed, "So you're telling me there's a chance!" after hearing the odds of his romantic interest were one in a million? That's the kind of unreasonable optimism you need in your corner.

They Provide Unconditional Support

Unlike your more practical acquaintances, these friends won't question your sanity every time you face a setback. They'll be there with words of encouragement, no matter how unlikely success might seem. Just like when Harry told Lloyd, "We got no food, we got no jobs... our pets' heads are falling off!"—yet they kept going. That’s the spirit of unconditional support you need.

They Help You Laugh at Yourself

Entrepreneurship can be a serious business, but it doesn't always have to be. Your cheerleaders will help you find humor in the absurd situations you'll inevitably face, keeping your spirits high when things get tough. Think about the time Harry and Lloyd drove a mini-bike through the Rockies in the dead of winter. "We’re there!" they shouted triumphantly, icicles hanging from their noses. It’s all about perspective and finding humor in the journey.

They Spark Creativity

Sometimes, the most innovative solutions come from the most unexpected places. Your unreasonable friends might just provide that off-the-wall suggestion that leads to your next breakthrough. "Hey, Lloyd, you wanna hear the most annoying sound in the world?"

It might not have been a genius business idea, but it sure was creative and memorable. Your friends’ wild ideas could spark that next big breakthrough.

They Remind You to Have Fun

All work and no play makes for a dull entrepreneur. These friends will ensure you don't lose sight of the joy and excitement that led you to start your own business in the first place. Like when Lloyd said, "Why don’t you eat up and we’ll tell ya," while pulling a prank on a diner. It’s the fun, spontaneous moments that make the journey worthwhile.

Remember, every great entrepreneur needs their own version of an enthusiastic, slightly unreasonable sidekick. They're the ones who'll believe in your million-to-one shots, who'll encourage you to take that leap of faith, and who'll be there to pick you up (probably while laughing) when things don't go quite as planned.

So, as you embark on your entrepreneurial journey, make sure you've got at least one of these Harry's, these cheerleaders in your corner. They might not always give you the most practical advice, but they'll give you something even more valuable: unwavering belief in your vision, no matter how dumb it might seem to others.

After all, in the unpredictable world of entrepreneurship, sometimes a little unreasonability is exactly what you need to succeed. So embrace the chaos, surround yourself with your own brand of cheerleaders, and remember - in the game of business, it's often the wildest ideas that win the day. And as Harry might say, "You know, Lloyd, just when I think you couldn’t possibly be any dumber, you go and do something like this… and totally redeem yourself!"

So who's your "Harry"?... When you figure that out, go give them a big thanks...