By Jason B. Lassner (May 2012)
This post is the third in an ongoing series that discusses my attempt to Not Die (a phrase coined by essayist Paul Graham) as a newbie entrepreneur. As part of learning how to keep moving forward in this endeavor I previously asked if taking on ambitious physical challenges would be useful.
The first of those challenges took place this past Saturday when I rode in the 3rd Annual Feed the Need charity bike ride in Highland, WI. It almost didn’t happen though, and that’s actually the topic of this post. Many times the learning takes place even before the ‘doing’ begins.
Despite a beautiful early spring in the upper Midwest and a late April event date, the weather gods turned sour and handed us a 40 degree morning with gusting winds up to 20+ mph and predicted drizzle. Yuck.
I was up for the challenge after having ridden my indoor trainer several times per week over the winter and then getting outside on the roads around Iowa City at least 1-2 times per week over the past month. I purposely rode hills and gradually increased my ride distance to just under 50 miles last Monday, with the last 20 of those straight into a headwind.
Mentally I felt clear and focused but as the weather forecast deteriorated last week I became more frustrated. How could a gorgeous string of sunny days in the 60’s suddenly change on the EXACT day of my scheduled event? What was the meaning of this? Who do I blame for this problem?
Not fair, not ok with me, and once Friday arrived and the work week was over it was decision time.
I had a lot riding on this event (so to speak) and absolutely did not want to bail. The forecast was so consistently gloomy, however, that bailing started to make sense to me. Regardless of my physical fitness and mental clarity how far was I really going to ride in those conditions? Especially once my clothes were soaked and the wind picked up and I was chilled to the bone?
What’s the point?
It turns out that was exactly the point.
“Smart” people, it occurred to me, would see the weather for what it was, find another ride of similar distance and/or challenge ASAP, and head home disappointed but dry. No point crying about the weather. Just move on. No worries.
I’m fairly certain that’s the choice I would have made had I been there alone.
Except that I would have secretly thought that “stronger” men would have showed up and ridden no matter what. Rationality might have gotten me home dry but not without worries.
This is the point in the sequence where having a trusted friend, what we call a Change Partner, changes everything. As I aired my tangled concerns to my business partner she listened carefully and agreed that it was a tough call on whether to show up for the ride or head home. She was certainly willing to go along with whatever decision I made and would have been supportive in either case.
When I told her that I was too emotionally invested to the situation to feel confident about my decision she thought about it and said, “In the end I just can’t see NOT even showing up.”
Right on, that. The thing about “bailing” in this context is that there is a huge difference between preempting the experience by heading home in advance based on objective “evidence” (e.g. clearly bad weather forecast) and showing up on the morning of the event to actually see what happens.
Would it be cold, windy, and wet as predicted? Would the roads be unsafe to ride? Would I ride 5-10 miles and get soaking wet?
None of these outcomes were certainties, just predictions. As entrepreneurial startup guru Steve Blank says: Until you get out of the building to actually test your hypotheses you’re simply guessing.
So we showed up on Saturday morning for the ride. It was indeed cold, windy, and wet, and the ride turnout was low, approximately 26 riders out of 40+ that had signed up. I don’t know for sure but I suspect any last minute riders who considered registering that morning decided against it.
Yet despite the apparent accuracy of the forecast and the hanging grey clouds and wet roads outside something unexpected was in the air. As we loaded up our bikes for the short drive to the ride site it became apparent that while the wind was gusting the air didn’t feel freezing on our skin. I inadvertently brought my middle weight full fingered riding gloves instead of my cold weather ones and forgot my balaclava for head and face coverage. These were potentially serious mistakes and yet the lack of cold bite to the wind suggested we would be fine anyway.
As we rode away from the ride start our first impressions of the weather conditions were confirmed: breezy and chilly with light drizzle, but nothing fatal in the air that suggested we should have gone home instead. Despite everything it was doable.
The ride itself turned out to be everything and more that I had hoped and dreamed to get out of the experience. The conditions stayed more or less the same but it never rained enough to soak us. I had planned to tackle the 100K route and once I got on my bike I stuck with my plan and went for it.
As the ride progressed I did a much better job of staying fueled (peanut butter is definitely on my list of 10 critical items if I ever get stranded in a remote location) and my conditioning and mindset paid off in spades.
In addition the fact that I almost bailed but didn’t paid me a bonus dividend: I felt like I was battling the odds and winning. It was fantastic.
I’ll say more about the ride itself in my next post but I’d like to end this one by emphasizing something basic and yet crucially important. I didn’t have an incredibly positive experience on Saturday because I “refused to give up” or because of over the top, Superman level fitness or Olympian stubbornness.
I’m too human and vulnerable for that.
In the days and hours leading up to the ride I was honest with myself about my concerns and the wisdom of riding that far in the cold and windy rain. What allowed me to untangle my concerns and show up in the morning to actually see what would happen is what we call Steadiness.
I expressed my concerns and was open to feedback from a trusted friend. This helped to calm me down and allow me to think clearly, which in turn helped me to see a broader menu of options than I would have otherwise. Sure, I could have justified going home on Friday, and I also could have insisted that “weather be damned” and I’m riding no matter what.
But once I was calm I could see that in between was the option to stick around and show up on Saturday morning and not come to any premature conclusions. If the conditions had been dangerous or otherwise insurmountable then I would have had to accept that such things are out of my control.
Of course you never know what will actually happen when you face your negative emotions and yet not allow them to rule your mind and make your decisions for you.
Trusting yourself and then “Letting Go” (e.g. following your instincts once you’re calm enough to think clearly) as we like to say ALWAYS serves you well.
Kind of like getting out of the building: unless or until you show up you’re only guessing.
Give it a try sometime and let me know what happens.

