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I have begun working on a talk that I will give in a week’s time at a local entrepreneur’s meetup in Vancouver. It’s a very short talk, 10-15 minutes in length. Not long enough to run through my story as an entrepreneur and hit all the anecdotal points about how persistence pays off. But I guess If they wanted that talk, they could listen to any entrepreneur ever.

Still, I want to speak of my experiences, and very importantly, provide a few things that an audience can take away and act on in their own lives. As it happens, I think I have just the thing. Something I’ve recently shared (subscribed yet?) in Episode 17 of The Steele Entrepreneur Show….

I’d like to take a stab at this talk in the form of my weekly newsletter.

I recently tuned into episode #50 of Jocko Podcast, where Jocko Willink and Echo Charles had the pleasure of interviewing Tim Ferriss. Tim has talked about his battles with depression, and even suicide in the past, however in this particular interview, he went deep into “the darkness,” I am sure glad he did.

We entrepreneurs have a tendency to tie our happiness to our success. If it’s failing, we are a failure. If it’s succeeding, we’re goddamn Mark Zuckerberg. Grief follows the former, and euphoria the latter. If you haven’t experienced this in business, perhaps you’ve felt the same way in a romantic relationship, or school—any situation where your happiness or self-worth is impacted by the ups and downs.

Now, what if that’s all you have? What if your school and perhaps your relationship are the only two things that you count on, the two things that supply you with 90% of your daily dose of happy? What happens when both go to shit and you don’t have anything else to fall back on?

It can happen a lot more easily than you may think. Take a second to think about where you get your happiness? You might be thinking now, “Well, I have my friends, my family, hockey, etc.” Those are some healthy options that might accidentally be abandoned.

Entrepreneurs tend to be obsessive by nature. They are obsessive in part because they’ve often been lucky enough to hook into something they are deeply passionate about. Add that to the risks taken (debt, credibility, etc) and tunnel vision is born.

When you go all in, those other things you used to draw on for happy can get lost along the way. They disappear under excuses like: “Friends will understand, right? Family is forever. Hockey will always be there – it’s not like I am selling my gear.”

But suddenly, find yourself in a place where you are ashamed of telling your parents and friends you are failing. You are so focused on getting your biz off the ground that you don’t make time for hockey.

What you now have is your business, and for example sake, the shell of an 8-year relationship you’ve tried to maintain with your significant other. And that’s where I come in. That was me in 2014. Before I knew it, I was pulling open my drawer of pills, and let’s just say I didn’t have a headache. The rest is history.

A lot has happened since then, and I’d like to leave you with a few things that you can do to avoid staring down the slightly-less-than metaphorical barrel of a gun.

  1. Don’t be ashamed. Share all the things. People want to support you. There is no shame in asking for help. Quite the opposite. The people I know who are most successful, ask the most questions. Remember that kid in class? $20 bucks says they had some of the best grades.
  2. Audit yourself regularly, “what makes me happy?” Don’t put your eggs in too few baskets. I am not advocating for work-life balance. Just a little diversity. A few things I found helpful: Group sports are a big help. Something about the comradery and common goal. Work on yourself. It’s important to respect yourself. Always dedicate a little time to learning and growing as a human being. Surround yourself with good people. Good in, good out.
  3. Lean on an objective third party. Someone whom you respect, who has life experience and you don’t fear judgement. If you find yourself in particular dire straits as I did, check out a psychologist. I’ve been seeing one for over 2 years, 2-4 times per month. It’s made a world of difference in my life. There is no shame in this. You’d be surprised how many of the people you know who’ve sought help, but just not said anything. Heck, give me a ring.

Bottom line, happiness isn’t to be taken for granted. It’s not something you can always count on being there. I am a super happy dude, but I work at it. The entrepreneurial path got sexy overnight, and I think we all just assumed we could do it. I think that is great, but it isn’t always what it’s made out to be, and we need to be aware of that. Perhaps just a little more self-awareness would go a very long way?

So, what do you think? What was useful? What would you change?

This post was originally published as a Quick and Dirty Newsletter. Subscribe here!

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