A few leadership lessons I was reminded of during an afternoon with Outward Bound

Leadership development and team building programs are full of small-scale physical challenges that require collaboration. Though they’re mostly just simple puzzles that follow similar models, having just participated in another a few weeks ago, I can say there are many lessons worth being reminded of.

Outdoor education nonprofit Outward Bound is one of those groups best known for these corporate training affairs, and LEADERSHIP Philadelphia, one of the older local civic training nonprofits in the country, had me again take part in an afternoon of such activities as part of a program of theirs I’m in. I want to share some of what I left the event thinking about back  on Sept. 18.

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I got married. Here’s a bunch of data on the experience.

I got engaged. Then I got married.

Between those two dates, I built one of the most involved spreadsheets of my life (yup, that’s something I think about). SACM and I used that spreadsheet to choose our wedding venue, predict attendance, invite guests, track purchases and monitor gifts. We’ve also been using it to give advice to friends.

Some of what we collected is private but lots of it is worth sharing for your own planning and budgeting purposes. That’s what I do below.

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7 events our news organization held for Baltimore Innovation Week #BIW15

For the fourth annual Baltimore Innovation Week, we at Technical.ly exercised a wide range of event formats. Years into exploring events as mission delivery and revenue accrual and marketing balance, we still need to get better. But I continue to be proud of what we accomplish.

To show that, I want to highlight a few event formats I was personally proud to be a part of during #BIW15, which featured 57 events during 10 days and close to 10,000 people — it was big, bigger even than last year.

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"Empty House" from August 2009 by Flickr user B Rosen via Creative Commons

Stop worrying about having too many people at your event

You won’t have too many people for the event you’re hosting. Make a bet on it.

Many of us will host events at some point in our lives — choosing a date, creating some programming and inviting people to come. I do quite a bit of this, some 50 events a year for work, a dozen or more a year for social groups I’m a member of and maybe that many among friends or one-off special get-to-gethers.

Often you might hear someone express frustration with the delicate balance, that you don’t want too few people there but you also can’t have too many. I’m here to help you: in very nearly every case, it’s better to have too many people than too few so that’s exactly how you should optimize. Don’t waste energy worrying whether you have too many people coming.

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How Open Source is Changing the World: my keynote speech at FOSSCON

To an audience of 100, I gave the keynote at FOSSCON, a one-day, open source conference held in Philadelphia for attendees from around the country this Saturday. (I also covered the event for Technical.ly here).

It was easily the most technical event at which I had a prominent speaker role — usually, I’m a side show to offer reporting background on a related issue. This time, I was closing out the event, which featured prominent open source leaders. But I wasn’t there to offer technical insight — which I don’t have — but instead meant to take reporting perspective and put it through the open source lens.

My title was “How Open Source is Changing the World,” and the argument was that open source software culture has shaped so many other changes happening in local tech communities — how technical recruiting gets done, why governments are pursuing open data, where tech businesses are locating.

I did an OK job at this.

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Christopher Wink receiving the 2015 Be Your Own Boss Bowl 'Self Made and Making Others' award

Temple University’s Fox School honored me with the ‘Self Made and Making Others’ award

I’m proud to say that the Fox Business School of my alma mater Temple University honored me with their third annual ‘Self-Made and Making Others’ award during the Be Your Own Boss Bowl.

The honor is a recognition for entrepreneurial work that helps others do the same. I gave a keynote address to students and other alumni, which I wrote out and shared below but mostly just used as notes.

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