Pushing Myself

Mike Drak

I LIKE CHALLENGING myself to do hard things. I guess it’s just the way I’m wired.

Recently, I started thinking about the hardest things I’ve done. Convincing my wife to marry me was hard. She was a tough sell. But eventually I wore her down and got the deal done—one of my best deals, by the way.

Attempting Ironman Cozumel at age 68 was hard and, even though I failed, it’s one of my most cherished memories. I enlarged a picture taken of me exiting the water after the swimming segment, and put copies up on the walls of my office and my pain cave in the basement. To motivate me, I also had a magnetized copy made for the refrigerator door.

Whenever I look at that picture, I think of Rocky after his first fight with Apollo Creed. My right eye is swollen shut and I have a look of pure exhaustion on my face. Every time I look at the photo, I break out into a big smile and laugh to myself. What was I thinking?

Believe it or not, writing a book was hard—perhaps even harder than Ironman. I’d never been any sort of writer before. But whenever I get emails from readers telling me my book helped them escape retirement hell, all the hard work feels worth it.

After much reflection, however, I think the hardest thing I’ve ever done was speak in front of an audience. I’m not sure when I developed stage fright. It might have happened when a teacher gave me a hard time after a presentation in grade school. Or it might be the imposter syndrome I suffered from while working in the corporate world. Or maybe it was a bit of both. It got so bad that sometimes, when I was in a meeting and they started going around the room doing the usual introductions, I would excuse myself, pretending to go to the washroom and coming back after they were done.

I turned down a number of promotions because of my fear of public speaking, and it ended up costing me a lot of money. Although I really wanted to and needed to overcome my stage fright, I couldn’t get past it.

But things changed after I wrote my first book. I knew I had to go on the road, giving talks to promote the book. I wanted to help as many people as I could figure out this retirement thing. That was my big “why,” so I finally had to deal with my stage fright. I was caught between a rock and a hard place, and there was no other way out.

That’s why I decided to join Toastmasters, which met every Thursday night. I remember the first meeting as if it happened yesterday. I was sitting in the parking lot, trying to find the courage to go in, but bailed and went home. The following week, I bailed again.

The third week, it was make-or-break time. I knew if I didn’t go in that night I would never be back. Thankfully, I finally made it into the meeting room. A friendly lady approached me right away and started up a conversation. They know first-timers are uncomfortable, and they try to calm you down.

I remember asking her to do me a favor. She asked what that was, and I said, “Could you please lock the door? At some point I’m going to make a break for it, and I don’t want to leave.”

Hearing that, she smiled and walked over to the door. I heard the lock click. That’s when the sweating and hyperventilating started. I was trapped and there was nowhere to run.

Staying there that first night was hard, one of the hardest things I’ve ever done. But it was also one of the greatest things I’ve ever done—because it was life changing.

I kept going back and, because of that, I don’t have to live with a lot of regret, wondering what could have been. Today, I really enjoy giving speeches and conducting seminars.

What I learned from doing hard things is that we’re more capable than we think, and we can accomplish some incredible things if we want it bad enough. I plan on doing more hard things with the time I have left. How about you?

Mike Drak is a 38-year veteran of the financial services industry. He’s the co-author of Longevity Lifestyle by Design, Retirement Heaven or Hell and Victory Lap Retirement. Mike works with his wife, an investment advisor, to help clients design a fulfilling retirement. For more on Mike, head to Check out his earlier articles.

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