Runs and Places

The Toughest Challenges Bring the Greatest Rewards

Running uphill in the rain is tough. Running uphill against 40mph headwinds in 38 degree temperatures with cold, driving, sideways rain that hits your face so hard the raindrops feel like needles poking your skin is downright brutal….. And that pretty much sums up what it was like to run miles 5 and 6 of the Mayor’s Midnight Sun Half Marathon in Anchorage Alaska this past June. Mile 7 wasn’t much better. The course turned off into a patch of woods, which helped a little bit because the trees provided some shelter from the wind, but since it had been raining all night and this part of the course was on a dirt trail instead of a paved road, all of the runners basically had to wade through a mile long patch of mud to get to mile 8. This was also one of the hilliest miles of the course so while I was struggling to make it through, I saw a lot of other runners around me slipping and falling, sliding down hills, and grasping at tree branches to try and pull themselves back up. Things leveled off and the weather cleared up a little bit over the next few miles, but by that point, my legs and feet were soaking wet, covered in mud and sweat and felt even more worn out than they usually would that far into a race. I already knew that my finishing time was going to be terrible but I pressed on through the last few miles, and somewhere in the middle of mile 12, I took a deep breath and gave it one last push to make it through the final half mile which was almost straight uphill. I looked up at the clock as I crossed the finish line and my shoulders slumped a little bit when I realized that I had just gotten one of my worst times for a half marathon ever.

Mile 7

Half Marathon…. or mud run?

When I think about some of the races I’ve done that were the polar opposite of that one, the 2008 Houston Half Marathon is the first one that comes to mind. This race is held in January, when the weather in Houston is almost always perfect for running, and that day was no exception. The course was also nice and flat, so with the mild temperatures, no headwinds to run against, and no hills to climb, it was probably one of the easiest races I’ve ever run. When I crossed the finish line, I did a fist pump into the air when I looked up at the clock and noticed that I had set a personal record for my half marathon finishing time. None of this really came as a surprise though – Houston is known for being one of the fastest courses in the United States and a lot of runners try to sign up for this race when they want to set personal records or qualify for the Boston Marathon (it’s actually become so popular that the race organizers recently had to switch to a lottery style registration system because so many people were trying to sign up as soon as registration opened that it was selling out in minutes and putting a major strain on their web servers).

Between the two races, Houston was obviously the easier one to run… but surprisingly, if you were to ask me which race I enjoyed more, despite the cold weather, wind, rain, mud, hills, sore legs and horrible finishing time, I would still say that Anchorage was the better of the two, hands down. There’s a simple reason for that: it was exponentially more challenging. I didn’t finish the race as fast as I would have liked to, but I still finished it, and in the course of doing so, I learned a lot about myself and what I’m capable of withstanding both physically and mentally which will help prepare me for even tougher challenges in the future. This is not a knock against Houston at all because I definitely learned how fast I could run a half marathon in that race, but the course itself didn’t really do anything to make me a stronger runner.



Completely unrelated, but Anchorage was also the only time I’ve ever stopped in the middle of a race to take a picture of a moose that was standing on the side of the course watching the runners….

Over the years, I’ve noticed a lot of parallels between running and my work life and this is a good example of one of them. When I think about the projects that I’ve worked on in the various positions I’ve held over the years, it’s always been the toughest, most challenging ones that have ultimately made me stronger and more confident. The projects that have required me to come up with creative solutions to complex issues that other people weren’t able to figure out are the ones that have strengthened my problem solving skills. The projects that required me to convince people in leadership positions that a solution I was proposing was truly the best way to do something even though it may not have been the most popular choice are the ones that have strengthened my resolve. And the times when my team members and I have had to go back to the drawing board at the last minute to fix unexpected problems that arose right before a deadline have taught me that any issue can be solved with a strong team and the right amount of determination.

Having to push myself hard to make it through a course like the one in Anchorage is what gives me the confidence to know that I can sail through a course like the one in Houston, not the other way around…. And in a similar fashion, knowing that I’ve had a high success rate in situations where I’ve been asked to take on leadership roles to help turn around projects that had completely blown their timelines and were hemorrhaging money is what gives me the confidence to know that I won’t have a problem completing smaller, more straightforward ones.

I’d be willing to bet that you’ve probably seen this in your own career even if you didn’t realize it. If you think back to all of the different projects you’ve been involved in at various jobs that you’ve held over the years, my guess is that you can probably divide most of them into two different groups: straightforward projects that you were able to complete in a short amount of time with little effort…. and more challenging projects that required you to think through tough problems critically, defend your stance on issues when your opinions may not have been popular, and figure out how to deal with setbacks and shifting priorities. My advice for anyone would be to make sure that you aren’t shying away from opportunities to work on projects that would fall into the latter group. These are projects that you might not enjoy working on at the time, but they’re the ones that you’ll learn the most from and they’re also the ones that will open up the most opportunities for you in the future. Think about it – if you were to go on a job interview tomorrow and you had to describe your biggest accomplishments to a hiring manager, would you spend more time talking about easy, no-brainer projects or would you describe the toughest projects you’ve ever worked on that were ultimately successful despite the fact that they required you to push yourself harder and deal with more challenges than you ever thought possible?

The only way to truly improve at anything is to be willing to repeatedly step outside of your comfort zone and deal with tough situations that challenge you. These are the situations you should actively seek out for yourself because if you deal with them frequently enough, then as you start to see some successes, you’ll also start to gain the mental toughness and confidence that you need to know that you can accomplish anything you set your mind to, whether it’s running a race in brutally challenging conditions or turning around a failing project at work that ultimately provides huge value to your company. After a while, you’ll also start to notice that taking on bigger challenges will open up new opportunities for you because each challenge that you successfully complete will add to a foundation that you can stand on when you’re faced with additional challenges that come your way in the future. If you make a habit of seeking out the toughest challenges you can find, the rewards will always be amazing.

5 thoughts on “The Toughest Challenges Bring the Greatest Rewards

  1. Pingback: The Toughest Challenges Bring the Greatest Rewa...

    1. Tom Leddy Post author

      Haha thanks! There’s actually a pretty funny story about the moose. A bunch of runners stopped to take pictures of her and just as a big crowd starting to form, a lady who lived in the area ran past and mentioned that the way her ears were pointed meant that she was starting to get pretty agitated because she probably had a calf somewhere that she was protecting. So we all took our pics and then made sure to get back to the race before we got trampled LOL! Glad you liked the post, thanks!!

    1. Tom Leddy Post author

      Thanks for the comment!! I’ve always said that when it comes to running, the toughest courses create the best memories later…. but it’s funny how that’ll carry over to other areas of your life too.

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