On Raincoats

I didn’t grow up wanting to be an entrepreneur. I, like most children, wanted to be a pro athlete and other such things. I can remember distinctly wanted to be a car mechanic at some point as well as someone who built bridges.

None of those things ever came to pass (at least not yet).

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Software: Never Finished, Only Abandoned


I’m iterating on Leonardo da Vinci’s very famous quote about art:

Art is never finished, only abandoned.

And I believe the application (pun intended) for software makes a lot of sense. I have been thinking about this non-stop since I released publicly my small indie app for desktop publishing and blogging, Desk.

I told a friend last night how it’s been humbling me something fierce with this particular app because I have a lot of blogging and writing friends who are using it and for whom I want it to work flawlessly.

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Time Required To Find the Next Job

A long-time friend and mentor of mine once gave me an interesting equation to consider when he was helping me with my next move. I had just gotten my ass kicked as a first-time executive in a Fortune 50 company and was looking to land on my next gig with the assurance that it wouldn’t be like the last time.

My friend, being an experienced executive recruiter with decades of experience under his belt, gave me the following equation to level-set my expectations:

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The Best Desktop Publishing App

When I first started blogging over 13 years ago I had very little intent and couldn’t possibly imagine that it would be something that would “stick” with me for years. I started small and there wasn’t any method or “strategy” or science to it in any way, shape, or form.

It was raw, unedited, and brutally honest. Over the years I lost some of that honesty as I started trying to be a “real” writer, a “real” blogger if you will, and I got lost in the mix of what I would suppose were attempts at becoming more “legit.”

I downloaded every widget, gadget, tool, app, and devoured “tips and tricks” from the real “pros” – I lost the love for the art and it became what we all dread will happen with the things that we love; it became work.

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Thrive as an Outlier

Do you want your app, your organization to thrive? Especially as a startup it is almost required that you become an outlier of sorts. But being an outlier can be lonely business as, per the definition, there just aren’t that many out there.

I love how Seth Godin puts this:

The easiest way to thrive as an outlier is to avoid being one.

He goes on to share succinctly that you must find the “treasured” few that will not only toe the line with you but walk with you on the very narrow path that you’ve decided to embark on:

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A Startup: 5+ Year Endeavor

I love this from Chris Dixon:

When you start a company, the most important consideration should be working on a product you love (a startup can be a 5+ year endeavor so if you don’t love it you probably won’t be able to endure the ups and downs).

A secondary consideration should be matching the skills of the founders to the market.

Mine for gold or sell pickaxes? Why not both? I think so.

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Leading Through Disappointment

Disappointment is part of life. It’s inevitable. Yet, many of us have never really learned to manage it very well (and you can think of 1,000 examples where you’ve seen this play out).

But that’s the thing: It’s easy to spot in others and not so easy to spot (and thus manage) in ourselves. The “solution” seems apparent and so obvious when we encounter a friend or a colleague that’s experienced a disappointment that we can barely control ourselves and we liberally share our opinions and thoughts on how to recover and restore.

Yet applying them to ourselves is another beast altogether as it’s infinitely more difficult, right? I mean, when the roles are reversed we may find ourselves rejecting most of that which is being offered even if we at least appreciate the sentiment and try. We just don’t want to hear it.

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