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I grew up in a really small town, in Northern Ontario. When I moved to the “big city” (Ottawa), I was incredibly timid. I had a hard time adjusting to the pace, and to the mentality of working in a bigger town.

The first thing I noticed was how people manipulated each other for personal gain. This kind of stuff happens everywhere, but it’s certainly much more pronounced in larger cities. There’s more competition, there’s more envy, there are more fake experts than true experts.

Some people might argue that in certain professions, expertise is determined by credentials. You can weed out certain people based on the letters after their name, or based on the school they went to. That certainly works for specific industries, like in engineering, or medicine. But, in private industry, and in business, letters don’t prove squat.

Even someone’s network can prove to be misleading if they’ve deceived their way into it. I’ve known many people who could sweet talk their way into an exclusive group, but who offered nothing in return.

When I was first starting out in the tech world, I listened to everyone, especially if they were in a position of authority. But, when I moved to Ottawa, I started noticing a very obvious problem with incompetence at the top. “You mean to tell me this person’s in charge?”

It didn’t take long for my rural skepticism to kick in. I started seeing this in other sectors as well. The art world is even more corrupt, but nobody pays attention to it because everyone’s fighting over a few dimes. In the tech industry, we’re talking millions up for grabs.

So, who do you listen to when you’re just starting out? It’s common for freelancers to join local business groups. I get why they do it. Freelancing can be an extremely lonely undertaking, so it’s natural to want to be surrounded by other people with ambition.

But, who’s advice should you take seriously? And, this is where most freelancers screw up. They listen to anyone with an opinion, especially if they have an authoritative title like “President”, “CEO”, or “VP of something”. Trust me on this: titles mean nothing.

Too often, new entrepreneurs listen to people who’ve had mediocre results. Artists do the same thing, by the way. They listen to peers that have no real world experience outside their city.

And that’s great if you want to be the best in your city. But, if you have aspirations to grow, or to perform on a global scale, you have to stop listening to people who are too timid to reach for the stars. 

Don’t get me wrong: getting a grounding opinion is absolutely useful. But few will be able to give you the right advice to spread your wings further than your city’s business luncheon events. It’s always easier to get rational advice than it is to get feedback on an idea that’s a bit ‘out there’.

I remember having people tell me to stop being so open. Stop being so “real” and start being “professional”. Fast forward a decade and now, being “authentic” is the new black. In other words, it turns out that people like being able to relate to other people. And as a business owner, if you don’t show them who you are, they might as well be dealing with a big box provider instead. Your authenticity is what sets you apart.

The people who have always been right with their advice in my life were almost always strangers. Why? Because:

  • Your friends will be too scared to tell you the truth.
  • Your acquaintances will discourage you out of jealousy and envy.
  • Your local experts only know the local economy.

Of course, these are generalizations, and even a rule of thumb can have its exceptions! If anything, I’ve found it beautiful to have the kinds of friends that will tell me the truth about stuff, even if I didn’t ask for it. It can take years to find those people, though. And even then, their knowledge is limited. If you have good pals, they’ll be there for you, but they might not be your best confidantes for business advice.

If you’re curious, here are the kinds of people I trust nowadays to give me the right feedback for business-related endeavours:

  • People who are doing exactly what it is that I want to be doing.
  • People who have challenged the status quo because they bring new ideas to the table.
  • People who have experience as non-traditional business leaders.
  • People who speak frankly.
  • People who have failed many, many times and who’ve finally figured it out.
  • People who are organized as fuck, and who know that ‘professionalism’ isn’t what you say; it’s what you do.

I like people who dream and take risks. I like people who speak their mind. I appreciate people who aren’t scared to share that they’ve made a ton of mistakes. The thing with kids these days who have found “winning formulas” for success is that it’s all short-term. I like people with scars and longevity. Those are the people I trust the most.