One of the more common critiques I receive from friends and colleagues is that I’m too self-deprecating. Too quick to point out my flaws or talk about challenges I’m facing. Too “humble”.

The argument has been that talking about one’s weaknesses or flaws (on a personal or business level) are detrimental. You lose opportunities this way. People don’t want to spend time around someone who’s negative, and talking about your rough patches can be perceived that way.

I’ve tried to absorb these suggestions over the years, and think about whether I should change how I converse with others. I’ve thought about the impact it has had on my personal and professional life.

But the conclusion I keep coming to is that it’s not a fault. I have many, many character flaws, but I honestly don’t think this is one of them. In fact, I would argue that I have experienced the opposite of what my friends think happens when you talk honestly about what’s going on.

I haven’t seen the lack of business opportunity. I haven’t seen people not wanting to spend time with me. It simply hasn’t been the liability you’d think it would be.

I think the reason is that what some have called self-deprecation or humility, many more perceive to be candor. And it’s become clear to me that candor has some huge benefits.

You’re okay, I’m okay. Everyone’s okay.

Most presentations I watch and most blog posts I read are full of bravado. They’re full of people telling you about the things you should do, based on the many and varied successes they’ve had. Occasionally someone will say something vague like “I’m not perfect, but” or “I’ve certainly had my share of mistakes, but”. But they won’t talk about them.

Get into a conversation at an event and ask someone about their business. My bet is that their business is going amazingly well. Customers are thrilled, investors are lining up, and all is right in the world.

At some point, folks decided that it’s a weakness to show weakness. The creation and preservation of one’s “personal brand” became of the utmost importance, and part of that was to not show chinks in your armor.

And so everyone you meet is amazing. Their companies are amazing. Their projects are amazing. No one has problems.

You could argue that it’s important to be positive. That an important part of success is to project success. That showing signs of weakness spooks people. In some cases (raising VC money comes to mind) you’re probably right.

But in many more instances, I think we could benefit from some more candor.

Candor builds stronger relationships

For me, candor has resulted in bonding with people at events where surface conversation rules the day. I meet fewer people but learn more about them. My decision to open up and talk about things my company is struggling or that I’m trying to get better at opens the conversation up. People feel like they have permission to share in kind. Underneath the whole “unnetworking” thing is a desire to get to know someone on a deeper level, and candor has been the key to making that happen.

But that’s very hard to do when both of you are talking about how amazing you are. You know it’s not true (about either of you) and they do too. But you play the game, project an image that you think you’re supposed to project, and add another business card to your pile.

The two business groups I got the most value out of in Chicago have been Jellyand the DIY-MBA group I was a part of. In both cases, friendships were quickly forged because of a spirit of shared candor. At Jelly people talk about issues they are dealing with in their companies and get advice. At DIY-MBA we went even further – we shared financials with each other, we shared our goals with each other, and we held each other accountable.

Note that candor as I’m defining it is not “being blunt”, which is often just a caveat for being a jerk and voicing your opinions in the most abrasive way possible. It is about being open about what’s important to you, what you care about, what you’re worried about. It’s about advising and counseling others out of love, helping them accomplish their goals and giving advice – using candor as a tool to build them up, not tear them down.

Those relationships were only possible because we all decided it’s more profitable to open up than to project a false reality.

Candor actually helps sales

One big lesson of the last year has been that I’m much better at sales than I thought. It was a huge concern coming into the year – my first company in Colorado was a failure chiefly because our sales skills were abysmal. But we learned, got better, and actually had an exceptional year from a sales perspective.

What I found was that talking about what you’re good at and what you’re bad at – even about the problems you’re facing – has led to more trust, not less. People are used to being told that whatever they want they can have, and they’re sensitive to being lied to. Being up front and saying “we don’t do that” or “this might not work” has made sales better, not worse.

Candor helps me when I fall

The problem with being amazing is that you can’t screw up. When your brand is predicated on being perfect and not having problems, issues become magnified. And no one magnifies it more than you do. You start to believe your own hype. Which is great when things are clicking, but when you falter it can be much harder to recover.

The success we had in sales actually led to some huge problems as we took on more work than we ever had before. I learned about my personal limits, which hadn’t really been tested before. I learned that my project management skills aren’t so hot, and my inability to delegate and rely on others came to a head. To be honest, I fell flat on my face a couple of times this year. And it hurt.

Being honest with myself about my weaknesses – even just acknowledging up front that I’m going to make mistakes and screw up, sometimes royally – has helped me get back up and try again.

In my career I’ve failed many times. I’ve made hiring mistakes. I’ve launched products that didn’t work. I’ve created interfaces that were less successful than what they replaced. I’ve organized many events where no one showed up. I’ve had a number of half-starts as an entrepreneur. I’ve closed down a business because I couldn’t sell. And I’ve made lots of sales and then screwed up because I didn’t plan well enough for the work.

Based on how other people talk about their careers and what’s necessary to be successful, I should be unemployed, homeless, and my wife should have left me. But that hasn’t happened. The mistakes lead to success. My interfaces are miles ahead of where they used to be. My products are better. My sales skills are much improved. And I’ve been getting better about delegating and managing projects.

In the meantime, being honest with myself has helped me recover, learn from mistakes and try again. And being honest with others has helped me earn a little bit of grace when I screw up.

I work my butt off to get better, and I try my best to learn from my mistakes so that they only happen once.

But I will continue to have failures. And I’ll continue to talk about them. It helps keep my ego in check, it helps me cut through the crap and connect with others, and it helps my career.

Next time you’re at a networking event or talking about your business, try to open up a bit. Share some of the bad along with the good. Worry a little less about projecting confidence and instead be confident enough to be humble. And don’t be surprised if good things come of it.

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