Obstacles are my allies

Twelve months of a global pandemic. Remember when we thought we might have to work from home for 4-5 weeks, and how crazy that seemed? 

In reading the book, Alpha Girls (more on this book below), one of the women that the book focuses on has a phrase that I simply loved: 

Obstacles are my allies.

Being a female in Silicon Valley over the last 30+ years, she had to embrace this mentality otherwise the weight of the roadblocks she faced would have crushed her. She persevered because she used those obstacles to her advantage. 

Shortly after I read that phrase, I was walking with my three youngest children on a path in the woods near our house. We came across a log that was blocking our way, and I saw an opportunity to teach my kids a life lesson. (Yes, sometimes they roll their eyes when I do this, but between us, part of my hope is that when they’re older they’ll share some of these lessons with their kids — ‘my dad always said…’ — that kinda thing 😎.)

So I pointed out that while this log blocking our path was indeed an obstacle, my philosophy in life is to try to think of an obstacle as an opportunity to improve my situation. I asked what they thought could be done to change this problem into a solution.

After some back and forth, one of them suggested that we turn the log sideways and use it as a guide rail for the side of the path that was on a steep incline. “That way, when we walk on this part of the trail, no one will fall down the hill,” my daughter said.

I moved the log into position and it worked just the way my daughter suggested. As we continued down the path, I once again reinforced the lesson to my children, saying, “In life, there will always be things blocking the path we are on. It’s up to us to either find a way around or use the obstacle to grow stronger and enhance the journey.”

I think I only saw one eye roll 😉

2020 felt like one giant obstacle

There’s no part of me that would ever suggest that the pandemic has been a good thing for the world. If I had the chance, I’d make a Thanos-like snap of my fingers and go back to last year and erase COVID-19 from the record books.

Alas, without such powers, the only way forward is through, and I thought I’d provide one example of how the giant obstacle of the pandemic became an ally for one part of my life.

I started my first nonprofit, 48in48, in 2015. From our first event in October of 2015 to the last event we hosted prior to the pandemic (October of 2019), every event was similar: hundreds of people working in very close quarters all weekend building 48 nonprofit websites. 

And then the world changed, and if someone were to suggest the idea of getting hundreds of people together for an in-person event it would sound more like a new Stephen King novel than an actual possibility. (Side note: King’s latest novel, Later, is terrific.)

However, 48in48’s Executive Director, Sima Parekh, saw this as an opportunity rather than an immovable obstacle. She matched up the biggest challenge with our organization (the logistics of hosting city-specific events) with the reality that in-person events were not possible and decided to test out a virtual event. The overriding belief had been that the magic of 48in48 was tied to the community of volunteers being together, in-person. And so in the past, any time the idea of virtual events was suggested, it was quickly shot down as being in direct contrast with what made our organization great.

Sure enough, after a few small test runs (MVPs, to use startup vernacular), we hosted our first global virtual event in October of 2020, and wouldn’t you know it was the most successful event we’ve ever had (500+ volunteers across 15 countries built 63 nonprofit websites in 48 hours)! And in 2021, we have six events planned, all virtual. (I talk more about this in a recent podcast episode.)

Here’s what the event looked like:

That is just one example of how an obstacle turned into an ally in my life. As an entrepreneur, I’ve always had to take the hits and figure out how to turn them into something positive. This, my wife would probably say, is one of my best and yet most annoying qualities.

The point is, we can’t control what comes our way, but we can control how we react to those things. Are you someone that sees a log crossing your path as a reason to quit, or do you see that log as a way to make your journey that much better? 

It’s in your control, and I believe in you :)


Recommendations: 1 app + 1 book

App: Fantastical

I made a fairly recent return to the Apple ecosystem (having been a Google Pixel user for years), and one of the benefits has been that I can finally use Fantastical. It’s going to sound insane, but Fantastical is a calendar app that comes with a monthly fee. Why pay for something that comes free with every computer, tablet, and phone you buy? The main reason for me, aside from the beautiful UI, is that it allows for the combination of calendar items and Apple Reminders (my preferred to-do app) in one view. It might sound crazy, but my calendar essentially dictates my life, and that’s a killer feature I can’t live without.

Book: Alpha Girls

I mentioned the book, Good Company, in my last post, so this time I thought I’d share the great joy I had in reading Alpha Girls by Julian Guthrie. The subtitle says it all: The women upstarts who took on Silicon Valley’s male culture and made the deals of a lifetime. I enjoyed reading the stories of these women, and it helped remind me that the business world still heavily favors men, and we need to recognize that and get to work changing it. A great line from this book:

The best revolutionaries are not the people who hate the dictators but [those] who empathize with the victims.

(Here’s a list of all the books I’ve read this year.)