As most of you can likely intimate from my infrequent blogs and tweets, I'm in the process of feeling out the next iteration of my career ambitions. After four years of idiosyncratically living part-time in the woods and bootstrapping an internet consultancy, I'm relocating to San Francisco proper, and my partners and I are beginning to intentionally exploring the next level.

One of the best things about this process so far has been actively seeking out advice from older, wiser, and more experienced people in our field. One of my constant observations — verging at times on complaint — over the past few years is that I don't feel there's a really good roadmap or template for what I do with my life. I'm coming to understand that's not really the case. Certainly there are particular novelties about my experience, but it turns out there are plenty of smart people out there who have done things not unlike what I'm doing now: working in a disruptive technology space with a lot of other folks, building a business and figuring out how to make the most of it all.

In hindsight, this is unsurprising. Anytime you think you're a really unique snowflake, chances are you're at least partly flattering yourself. Even though there aren't many people from my immediate peer group that are doing comparable things, there are plenty of people on the scene here in good old Silicon Valley who are.

And, in getting to know some of these people, it's reall nice to get some external validation. Left to my own devices, I will always expect more of myself, always in some way unsatisfied with my achievements. It's easy to sit here in my office and see all the things I haven't done, all the opportunities we missed, all the work that's still left to do.

But the outside voice reminds me, in speaking of what we've built, "you know, most people can't do that."

Packing up my room here in Westhaven, pulling up lots of interesting finds from the past four years. I saved a ton of business cards from all the various conferences I've been to since moving to California. There are some good postcards, some interesting letters from interesting women from the past, and a little parade of old wedding invites, baby pictures, and christmas cards.

It makes me wistful, reviewing these artifacts. I don't want to change my past. Nor do I want to go back and repeat it. But I do wish — especially with baby pictures and the like — that I had more time to be there, to be a more active participant in all the wonderful happenings within my extended network.

I'll also miss the hell out of this house; more than anything Kellymundo and Ace.

I think before I started becoming a real entrepreneur I had an alternate track that would have put me here more to stay, and while I'm happy to be where I am and headed where I'm headed, I'm also just a little sad and curious about that other track.

Hopefully I'll have many happy returns to this little piece of Redwood Paradise. I'm sad to be leaving.

I spent the past four days on the Island of Oahu, Hawaii, doing my part as a groomsman for the blessed union of Jesse Austin Dean and Gina Maria Long. Everything went off incredibly well. Weddings are sometimes occasions for people who don't see (or really want to see) one another very often — e.g. divorced parents — to clash. But there was zero drama, many kind words were said — my man The Girth burnishing his credentials as a first-rate orator — and a good time was had by all, not least the bride and groom.

Most of my experience was (rightly) about these other people, but it was pretty good for me too. Not a vacation, but a chance to decompress for 72 hours. Touristas aside, my cliche expectations are much exceeded by the reality of Hawaii. The North Shore felt like a place to spend some more time without a schedule or obligations, and I enjoyed being an out-of-place bum in Waikiki for a day.

Also got a lot of reading done. Finished the Žižek without uncovering significant further revelation, and then slurped up the much less dense Geography of Bliss, which was a good pick for a quick pseudovacation. Eric Weiner, a foreign correspondent from NPR and self-professed "grump" with an overdeveloped sense of irony, travels the globe to very happy (and unhappy) places, in search of what makes them so. Occasionally strenuously clever tone aside, the content is good food for thought. I was particularly struck by this passage at the end of his visit to the recently-ultrawealthy Quatar:

Having a lot of trouble focusing, my mind skittering around the edges of what's to be done. Feels like personal failure. I'm a little sad, caught here outside the perimeter, alone.

In the grand scheme of things I know I'm one of the luckiest people alive, that This Too Shall Pass, but it's just not a great Sunday morning.

On the one hand, I believe that good things require some amount of pain and sacrifice — A Grand Don't Come for Free, after all — I also believe that the most important thing is to stop struggling.

When struggling, there's a pretty good chance that "You're Doing It Wrong."

Not sure how to do it right though.

Not super happy that Rina is moving to London next week.

Not feeling very much in the flow, or where to go to get picked back up into the stream.

For the moment, it's a world of TODOs and trying the best you can, trying the best you can, hoping the best you can is good enough.