How to handle mistakes and move on with your life

Lately I’ve been spending a lot of time trying to impress my girlfriend’s parents. I want them to like me. I know for a fact that they didn’t like her last boyfriend and I feel like setting myself apart from this dude is really important. So last weekend we offered to watch their horse farm while they went to visit their other daughter.

No horses died (phew!) but I had a little accident with a tractor. While mowing the lawn I ran it into one of their barns and tore down a couple of sheets of siding in the process. This isn’t a cheap barn either. Not the kind that you can hammer a couple new pieces of plywood to at least. So I started to panic.

I’ve made a business out of helping people, I mean, that’s basically what a Community Manager does. However, mistakes of the “whoops my link doesn’t work” variety are the kind that I deal with them every day. Mistakes like “gee, I totally mangled your dream barn” aren’t really my forte.

Confront things head on

My girlfriend is a saint. She offered to tell her parents about the barn siding for me. I was really close to letting her do that because I’ve seen her mom pissed off but when she got on the phone I found myself reaching for it.

At my first post-college job I made the mistake of letting someone else deliver a mistake to my boss. Nothing makes you look less capable than having somebody else communicate your own failures.

Just look at all the celebrities and politicians that have “people” answer for their mistakes and it just ends up blowing up more.

Provide a solution

After I delivered the bad news about the barn I immediately offered to pay for the damages and drive an hour outside of Madison to do the repairs myself. I’m still waiting on the bill with fingers crossed that it doesn’t leave me drinking Busch Light for the next month, but the fact that I took ownership over the solution kept me from crippling myself with anxiety.

The great thing about making mistakes is that you’re offered a new opportunity to prove yourself by fixing the mistake. Because let’s face it, people fuck up every day at work and in their personal lives. The only thing that separates the winners from the losers is whether or not you try to fix the problem or sit around whining about it.

Do something to show that you really care

I bought brunch. I also said thanks for everything that they do for me. And I think that I’m allowed to mow the lawn again which is something that I was really worried about. I love to mow lawns and their lawn is the Mecca for landscapers.

It all comes back to being accountable and not being a whiner. There’s a little bit of a whiner in all of us though (some of us more than others). For a moment we all question whether or not we can’t point the blame somewhere else and avoid catastrophe, but I’m starting to realize that the real catastrophe is not being able to handle that one moment when everyone finds out that there is a problem…. and yes, you are the one behind it.

Learning to deal with failure is one of the hardest things that young pros have to learn. If it’s any consolation, they make for some really great stories after they’re over.

I’ve never had a mentor, and that’s okay

Penelope Trunk told me that she couldn’t be my mentor. “You’re too difficult,” was what she said. At the time I didn’t care because I thought that I hated her. Emotions run high in early-stage start ups. Ours was no exception.

Over time I realized that I didn’t really hate Penelope. What I really hated was my lack of confidence when becoming self employed. Once I figured that out, we became friends.

A friend. Not a mentor. I have learned plenty about myself just from being around her, but I don’t want to be like her. I have a lot of people like this in my life.

Trial and error is my mantra. I’ve always learned things the hard way. It makes sense that I would ally myself with people I don’t typically agree with. Things are more interesting that way, and you learn more too.

When is the last time that you learned anything about yourself without conflict? The biggest lesson that I learned in 2009 was to push back when people are expecting too much out of me. I learned to set expectations for people, and if they didn’t like it, tough luck. I didn’t learn how to do this through someone I wanted to be like, I learned it through people who are nothing like me at all.

In essence, the big epiphany moments, the light bulbs, every “a-ha” was something that I came to when I stepped closer towards people I didn’t want to be like and further from people who made me feel comfortable. Chaos has been my muse, and so far she’s treated me quite well.

Life would be boring without the people that make us tick. They force us to think in different ways because we want to debate their ideas. Some days we win, others we lose. In the end, we all learn something.

I’ve never had a mentor in the traditional sense, and I think that maybe I don’t need one. I’m not the type of person who needs people to hold in high regard. I just need people who push me. And usually the best person to do that is someone who is not very much like me at all.

On thinking that I’m going deaf, and confrontation

I almost always cut the first paragraph out of each blog post. I do this because my first paragraph rarely accomplishes anything other than self absorption. Writer’s masturbation, if you will.

I’m telling you this because you might spend a lot of time beating around the bush, too. Sometimes we end up hurting ourselves when we indulge in such tomfoolery.

I spent two days in Tulum, Mexico convinced that I was going deaf. I went diving through a bunch of reefs and caves. I was convinced that all the pressure changes knocked something loose. It’s stupid, but these are the kinds of neurotic thoughts I’ll do back flips over on a daily basis.

It took me two days of blue funk to pony up and go to a Mexican doctor. I barely understood his broken English, but he squirted a syringe of what looked like club soda into my ear, then ten minutes later pulled out a ball of wax. He showed me the dime-sized wad before tossing it down the drain and writing me a bill for 1,299 pesos.

The money didn’t matter. The time I spent worrying about the outcome cost me two days of vacation, and that did matter. I could have been sipping tequila on the Riviera Maya—not a care in the world—but I spent two days comatose from my own angst instead.

I want to learn to be better at confronting things early. I want to axe out the stage of fear where I let hours decay while I think about ungodly outcomes. I think if we all learned to do that a little better, we’d be a lot happier with our lives.

Sure, it’s quite possible that you’re the ass-kicking lord of confrontation—by god you better be blogging and sharing some of that wealth—but I’m not. And if you’re anything like me, please raise your glasses, then go schedule some time to reflect on the things you’ve been brooding over for way too long.

Like maybe there’s tension at work and you’ve been avoiding butting heads because it’s unnerving. Confront that.

Or maybe you just haven’t been blogging because you’re afraid that what you say will suck. Confront that, too.

Whatever it is that’s holding you back from living life, unabridged, confront that shit and move on. Once you’re done, you’ll feel stupid for not doing it sooner, but relieved that you finally did.

A lesson in being stuck, and getting unstuck

When I adopted Charlie, it fit. I’m the type of person who likes having someone to take care of, and when I was working from home I felt less lonely. I had always loved having dogs, and this was going to be the first dog that was all mine. Up until last weekend when I finally gave Charlie away, we were always able to adapt to the changes we had to face together.

When Brazen Careerist moved out of my apartment and into a real office things changed, but we were able to adapt. When the business started getting more demanding, we were able to adapt too. Even when we moved into a 900 square foot apartment with my girlfriend, who initially didn’t like dogs, we adapted.

The change that pushed me over the edge was that I felt stuck. Even worse, I felt as if the dog was stuck too. He showed me that he felt stuck by pulling used coffee filters out of the garbage, tossing the grinds all over the carpet or by opening the refrigerator and eating multiple sticks of butter and then vomiting.

Meanwhile, I showed him I was stuck by spending money. Three-hundred dollars a month on average to be exact. That’s chump change compared to what parents spend on daycare for their kids, but for a twenty-something making startup money, doggie daycare is a bitch.

Pun, definitely intended.

When Charlie first came into my life I wrote a post where I said, “you couldn’t take my dog away from me with an army behind you.” I really believed that, and I can honestly say that I tried everything to make it work.

Giving Charlie up was easily one of the hardest things I’ve ever had to do. There are days when I regret the decision. There are even days where I look down by my fireplace and wonder why he’s not there. But I really have to believe that letting him get unstuck was the right thing to do. Hopefully, it will help me get unstuck too.

One of the most important things I’ve learned from being in a startup is to not let yourself get stuck. When people get stuck, businesses fail. Give it the proverbial “college try” of course, but if it doesn’t work, move on.

Such is the same in other aspects of our life.

I was thinking that at the end of the post I might tell you to not get a dog if your life is unstable, like mine. But I don’t really think that’s right. In fact, a dog might be exactly what you need.

When I got Charlie, I was lost in a lot of different ways. I was in a new city. I had been struggling to find meaningful relationships with people. I wasn’t even sure if Brazen Careerist was going to work. Then I adopted a 2-month-old chocolate lab puppy. He didn’t fix any of my problems, but he reminded me to take joy in the more simple pleasures of life—something that I had forgotten.

So who am I to say that having a dog isn’t right for you? During the two years that I spent with my own dog, I’ve experienced so much joy. And even though after two years of fetching, chasing and cleaning up poop our relationship no longer made sense, I wouldn’t trade the time I had with Charlie for anything.

An Inauguration Day stranger, Memorial Day promises and the inconvenience of change

Four months ago, I was sitting in a bar with Ryan and Dan Healy, and Penelope. It was Inauguration Day. We watched our country make history swearing in the 44th President of the United States.

The room was a can of sardines, but more optimistic. Tangled in a motley web of businessmen, congressmen and college students, we parked it next to a middle-aged bald guy. Pulling out a shot glass from his jacket pocket and slamming it on the table, he asked the barkeep to pour some whiskey.

“Hey,” he said. “Would you guys like to take a shot with me?”

Dan and I looked at one another, then back at the guy. “Sure,” we decided.

“It means a lot that you both are doing this with me,” he said. “I’ll tell you why after Obama takes his oath.”

We sat there, quietly sipped on beers, listened to Biden take his oath, then Obama. Looking over at our friend, I saw tears.

“Cheers,” he said. We took our shots. I forgot what whiskey tasted like midday on a Tuesday. Closing my eyes for a moment, I regained my composure. When opened them, the man was pointing to a pin he was wearing on his chest, a young man in uniform holding a puppy.

“This is my son,” he said. “He died in Iraq four years ago.”

He told us how passionate his son was to go into the Middle East—keen on making the world a better place—only to find himself appalled by how everything was being done. He couldn’t wait to come home and dedicate his life to changing America’s foreign policies.

He never got to do that, but his fortitude lived on through his father. Obama’s Inauguration—in his eyes—was the catalyst for change that his son had dreamed about.

“On Memorial Day,” he said, “do me a favor.”

“Tell my son’s story to someone … anyone.” He just wanted his son’s story to be told. And today, I’m doing the best I can to live up to my promise.

During the month of May, two amazing bloggers, Sam Davidson and Matt Chevy, teamed up to get young bloggers talking about change. I couldn’t think of what to write about. Then I remember the promise I kept to that stranger on Inauguration Day and the lesson that I learned.

It has nothing to do with politics, or foreign policy, or Republicans versus Democrats. It’s about the power each of us has to make a difference today, right now, if we’re devoted enough and perseverant enough to make things happen. It’s a fragile gift, because we never know when that chance might be taken from us.

I’ve been thinking a lot today about the people I know whose dreams of cultivating change were cut too short. Like my friend Kaity, who might have lived on to help save the rainforests if she didn’t die of an over dose two years ago. Or my friend Chris, who would have made one kick-ass electrical engineer if he didn’t die tragically in a fire before he even graduated college. And of course, Sgt. Mark Allen Maida … a total stranger to me if it wasn’t for his father.

As another Memorial Day drifts past, and we all go back to work, school or whatever else we do with our time, let’s try not to forget how easy it is to fall back into idle behaviors. Let’s try to remain focused on the things in our lives that we want to and need to change.

Change isn’t enclosed in bubble wrap. It’s not going to wait until we’re ready to commit. And when the chance has gone, we rarely get a chance like it again.