By the time something *has* to be solved, it’s probably too late

I’m not a procrastinator, which is no small feat, considering my father and my sister both are.

I take a lot of pride in planning ahead on challenges or opportunities. Sometimes that runs counter to others, who are more to sitting on deadlines. Of course crashing into a deadline happens to us all but the reliance on them concerns me.

That’s because, as I’ve been thinking lately, if you wait for something to have to be solved, then it’s often too late. You can’t creatively or find opportunities for efficiencies. Once the deadline is here, it’s broken and you aren’t going to be able to fix it.

So? Change what a deadline means to you. If something is due on the 15th, your deadline must be the 10th and so you better get started on the 5th. Then you can be the person you say you are.

4 lessons from sports stars that stuck with me as a kid

For all the meaningful sources of life lessons I received as a kid, from my parents to religion, and the many shades of the Golden Rule, I was still a sports-crazed boy growing up in the 1990s.

That means I internalized a lot of advice from athletes, whether or not they actually ever said them (sports quotes are full of apocryphal and fictitious claims). I was amused recently to think of a handful of very-90s-era memories I have about lessons from North American sports legends. In addition to being stuck in time, this collection is funny because I am so far from a knowledgeable sports fan today.

So these are corny for all sorts of reasons. Yet I do find myself thinking of these even today.

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You’re adopting a puppy

For every project you take on, any commitment you make, you’re agreeing to a longterm relationship. Other people will depend on you, habits will form and roles will shape.

It’s like adopting a pet, as a colleague and I say to each other sometimes. Are you willing to walk the dog? To feed it and give it water and be willing to spend the energy, time and money if it gets sick?

I say that to myself when I want to start something new, and I find it helps influence my thinking. If I think of the longterm requirements and still want to move forward, then I will. If not, well, there’s no use to start at all. (One way I’m working to say no more often).

What I accomplished as a Pen and Pencil Club governor 

I first visited the Pen and Pencil Club in January 2009, as a spunky, 23-year-old. After visiting frequently, I finally became an official member of the country’s oldest surviving open daily press club in early 2012.

Then, in 2013 I ran and was elected to the club’s board of governors, with some encouragement from then club President Chris Brennan, a celebrated politics reporter and columnist who worked hard to grow the kind of members in the club. I was growing a reputation with Technical.ly and an active local organizer of the Online News Association.

I was proud. I learned a lot, and I put a lot of effort into being a board member. Next week, rather than run for a fifth term, I am stepping down. Here I share some of what I accomplished during the last four years.

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With $1.67M in 2016 income, here’s what I learned with Technically Media

Harvard University’s Nieman Lab journalism trade publication profiled last week Technically Media, the digital media company I cofounded, for the first time since 2012 (that year we got both a profile and an expansion look).

This new profile, which you should read, seemed like a grand opportunity to revisit the check I made in 2015 when we surpassed $1 million in revenue for the first time. So to supplement my professional accomplishments of last year, I wanted to share a few notes included in the Nieman Lab report I find important.

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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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Why I’ve (slowly and modestly) paid more attention to fashion for professional gain

Even in high school, I had it in my head that buying new clothes was vain.

Picture my mother pleading with me to let her buy me pants that fit me. At some point I realized that she had started sneaking in new pairs of socks and throwing out my old ones with holes. One of the first places I went after I got my driver’s license was to a thrift store, afterward proudly showing my parents a $5 suit I bought (and wore way later into life than I should have, like at our closing party at Philly Tech Week 2012).

While my teenage friends cared about clothes, I was defiantly disinterested in any of it. I was proud I saved what money I earned and perhaps prouder of how little I ever asked my parents to contribute. (For their part, they were more often embarrassed of my taking hand-me-downs from bosses and friends. They were worried it might look like they weren’t taking care of me, even though they most certainly were. I had one of the most loving households I could imagine, which might be why I didn’t want to ask them for anything else — look at how they helped me pay for college.)

But then I got older and entered the workforce, where the first impressions you make aren’t cast aside by the whims of youthfulness.

It took quite a few experiences as a professional for me realize that there’s a balance between spending too much money and time on clothes and too little, and I hadn’t found it. That’s when I had to make a change.

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You can only succeed in building a business if you know what’s success: ‘Like a Boss’

The hard part of entrepreneurship may not be succeeding, as much as it is about deciding what success if for you. That might be the cause of so much argument about this moment of entrepreneurship — should it be wealth, mission, personal satisfaction, longevity, legacy or something else? More likely, it’s a mixture of them all, with your own happiness the leader, and deciding on that balance is part of the process.

But the point here is you can’t ever succeed in anything (including building your business) unless you know what you want to happen. That way you can optimize for whatever you most want.

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Every entrepreneur should be building a monopoly: Peter Thiel

Paypal cofounder, public intellectual and global tech entrepreneurship leader Peter Thiel is thoughtful in his perspective on economic growth. An interview with him was on our last Technical.ly podcast and an even longer conversation he had on a different podcast was even more enlightening.

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Obamacare more than doubled my company’s healthcare costs: here’s what we did

Following the July 2014 final rules implementation of the Affordable Care Act, my company Technical.ly was impacted more severely than we expected. This is not a political article — I am not opposed to Obamacare — this is a small business owner’s experience.

With just eight full-time team members (excluding, of course, our part-time independent contractors), I am solely responsible for managing our healthcare coverage plan, and while I tried to prepare for what the change might be, I wasn’t ready for our costs to more than double, and, for some plans, almost triple. Here’s what I learned and what we did.

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