In episode 23 of Back to Work, my friend Dan Benjamin argued it is not possible to do two things really well at the same time. Specifically, Dan explained that there simply aren’t enough hours in the day to seriously pursue two different big things. He used the example of starting an iOS app business while holding a day job. Dan made a good case that the attempt to do two things well results in you sucking at both.


I’m doing a lot of things at once. Am I torpedoing myself? Dan’s argument led to some soul searching about what I’ve been up to lately. I simultaneously agreed and disagreed with Dan throughout the show. At one point Merlin Mann used me as an example. I practice law by day and write technology by night. Dan explained that I didn’t count because I’m not a, “normal human.” That’s the one part that Dan got wrong. I’m very human and this stuff is really hard.

A Very Regular Human Indeed

I laugh when someone refers to me as a productivity guru. I am a mess. My mother chose well when she named me David. I spend my weekdays in the trenches with my clients against a seemingly endless stream of Goliaths. I spend my free time (the weeknights and weekends Dan was talking about) writing for MacSparky and podcasting with the Mac Power Users. Add to this my family, friends, and other social commitments and I quickly find I don’t have just two things. I have six or seven. That is my normal juggling routine. Now add to this the spinning chainsaw that is a 25 chapter book, due in just a little over a month, and you can see how I am well and truly screwed. Or at least it would seem. The thing is, right now I am having more fun than ever.

Saying No

Saying “no” is something I’ve only recently figured out but, like a religious convert, I’m exercising this particular muscle plenty. If you want to juggle, you have to learn to say no. Even jugglers have their limits. There are degrees of difficulty in saying no. Television and video games are the easy ones. The day I decided to stop responding to every MacSparky e-mail was a tough “no”. (I still read everything you send me.) It gets even harder when you turn down opportunities. In the past six months I’ve turned down some great opportunities including writing for some really smart people, sitting on an American Bar Association planning board, and expanding my career. I don’t have any regrets with any of those, but they weren’t easy. The real corker, however, is saying no to your family and friends. That is a fourth degree no. This stuff is hard.

The key to it all for me is balance. I try my very best to give the things and people I love attention and accept that it is not possible for me to be all things to all people at any one time. I’m also not too hard on myself. I do my best and try each day to get a little better.

Where Dan’s words ring true for me is this very month as I push to complete a book. It is this extra commitment with the obscene amounts of extra time it requires that I get Dan. Now things are nuts. The next month is going to requires me to say no to some things I’d rather not. It is a temporary thing and will pass soon enough. If every month was like this one, though, I’d fall apart, just as Dan predicts.

Big and Small Touches

Wouldn’t it be great though if I could constantly juggle all of this? If I could run a law practice, blog, podcast, speak, and write books and not go insane? That would make me awesome with my very own superpower. That, however, would also be bullshit.

Writing the book is my edge case. Normally I seem to get by just fine with the law practice and MacSparky. I think, for me at least, this juggling act isn’t a super power but instead a selfish thing. I really like everything I do right now and I’m addicted to the big and small touches.

Just looking at my law/MacSparky juggle, I see these two things scratching very different itches.

I became a lawyer because I enjoy helping people. Stop laughing. You’d be surprised how many lawyers find themselves in this profession for exactly the same reason. People come to me with some really big problems. My clients need help and I can make the difference between pulling out of a nose dive and making a big smoking hole in the ground. My work as a lawyer has a major impact on their lives. Those are my big touches

MacSparky, on the other hand, leads to many small touches. I get e-mails from people all over the world explaining how some little thing I posted or said made their lives better. I love those small touches. When the Mac at Work book shipped, I received an e-mail from a single mom who explained how she used a bunch of my workflows from the book to shorten her work day, saving her about 10 hours a week (500 hours a year) for more time with her daughter. When I wonder why I’m working so hard on this next book and saying “no” so often, that e-mail is why. Both the big and small touches that mean a lot for me.

Dan is Right

Despite all of the above yammering, Dan is right. You really can’t give two things everything. The trick in all of this is finding that tipping point when outside interests go from being simply a hobby or dabbling into the pedal-to-the-metal Next Big Thing. Recognizing that moment and having the guts to jump on it is key. That is what I think Dan was talking about and he is absolutely right. My only qualification is that this idea of just one thing shouldn’t prevent you from dabbling and hobbies. You never know where those things might lead. (I think Dan would agree with me on this.)

Since I’ve accepted Dan’s argument, I’m agreeing that if I did just law, or just wrote about technology, or just podcasted, I’d no doubt be able to commit more energy and be better at the one thing. However, I’m still not interested in picking just one. Maybe I’m too gutless to jump but I don’t think that is the case.

Emerging from this rabbit hole, I realize that at this point in my life, I couldn’t imagine myself giving up the big touches or the little touches. I’m not willing to jump on just one thing because I’m enjoying several things way too much. My life is more enriching now because of all the things I do. In other words, I intend to continue juggling.