So I can’t help myself–I’ll take on something big, even if it’s “out of scope” from regular work.  But time and again, the value I get from that effort is so much greater than 100 little projects.

When I look back at  what’s been really meaningful for me, it’s been cases where I went all out.  Sometimes it was a few extra hours on a task that could’ve taken a half hour.  Others it was writing an eBook or a content site instead of a simple blog post.  Perhaps it was even turning AwayFind from a hobby into a product, team, and business.

This isn’t a prescription to  "go big or go home."  There’s a balance, and a point of diminishing returns for all of our activities.  It’s just that, for me at least, the reward from creating something that takes the extra work far outweighs the effort.

This may all seem obvious, but I’m sharing this now for two reasons:

• Perhaps not everyone thinks this way.  I’m genuinely curious—a lot of people would prefer to take on challenges with less risk-reward involved, but have they seen just what kind of reward is at stake, even if it’s just personal fulfillment?
• To talk myself into creating more.   I feel that I can offer much more value than I’m doing now, and getting started again here is likely the first step for many of the creative projects I’m interested in.

That first step is tough, for me as much as for you.  But I’m taking it here as I want to create more.  Do you want to create more, to do something big?  What’s your first step?

Flickr photo credit: gdudg

They were engineers, and their arguments were logical and comprehensive, but fundamentally misguided.

Their arguments were of the "this won’t cure cancer" variety: they explained that my proposed solution would not be definitive, just like most research on cancer targets just a subset of people.  Trying to cure cancer is about making progress, until maybe someday we arrive at the true panacea.

Here were the specific arguments presented to me:

This pattern doesn’t always indicate [that path], so we can’t recommend [that path] to the user"
- paraphrased from a conversation with Person A

But the pattern (which was easy for our software product to identify, but nearly impossible for a human to recognize) is accurate more than 90% of the time.  So, as far as I’m concerned, 90% is good enough to recommend a path to our users.  This solution doesn’t address a life or death problem, but even if it did, it’d still be the best recommendation.

It has the potential to be successful, much like businesses that sell anti-aging cosmetics to aging women.  The customer understands that the problem is unsolvable, but readily pays for a combination of A) buying time on the hamster wheel, and B) fooling themselves for some amount of time.
- verbatim from an email from Person B

Once again, this colleague is comparing a working solution to a fantastical cure-all.  My solution wasn’t tricking people, it was just solving one portion of a bigger problem.  If that portion weren’t a problem on its own, then perhaps I’d be selling snake oil to fools.  But if that portion is legitimate (and he does believe that there are benefits) then I’m making real progress for real people.  Even if I’m talking about productivity rather than saving lives.

Someday all of us can hope to cure a disease or overthrow a nascent industry.  In the meantime, it’s both reasonable and right to push society forward in small and meaningful ways.

Aim for progress, don’t get caught up in perfection.

Flickr photo by wili_hybrid

In 2012, I did give my best.  What was challenging, even more than the fight forward, was staying sane enough to let go and to keep moving forward.

When things are outside of your control, when they don’t work out, you’ve simply got to push forward with your business and with yourself.  At work, that’s easy—keep doing the marketing, keep following up on the leads, keep building a great product.  But outside of work, it’s not so obvious.

When I looked back on 2012’s challenges, I mentioned that there were 3 things that got me through it.  Here they are again, this time with explanation.  I offer my formula to you, so you too can push through:

1. Take Care of Yourself

When shit got hard in 2012, I hit the track.  Without realizing it, I found myself in particularly good shape.  It’s been a (not quite) joke in my relationships that when things are peachy-keen I have nothing to write about.  I’ve uncovered a second truth—when things gets tough, I run more, too.  Try it—hard running feels a lot better than a marathon of Breaking Bad.

Beyond running, I went camping and kayaking and generally surrounded myself with the beauty that is the Bay Area.  Nature physically changes me, and a day away is a chance to get to know friends much better than breaking bread.

When it’s rainy or late, writing has always been a help for me.  If I’m too tired to write, I’ll simply record to my iPhone.  It’s amazing what sharing it all can do, even if it’s just sharing with yourself.

Lastly, I added chess to the mix this year.  Though I generally avoid games, something about the thinking that chess demands just felt right to me; it’s an escape that I’m comfortable with.

2. Find the Company of Friends or Family

As I mentioned, I try to stay active when there’s a lot on my mind.  I also try to surround myself with friends, even if it’s just their company when we’re working across from one another at a cafe.

I get a lot out of doing for others.  While it can be frustrating if they don’t reciprocate, I’ve come to accept that I’m the one who will likely reach out more.  We all have our own approach to friendships, and I know my friends appreciate when I include them.

While there are some ways that a friend can’t replace a significant other, it’s surprised me just how good a job they can do.  Whether it be reading together on a weekend morning or late night dancing or cooking together, most activities don’t have to be reserved for lovers.

3. Never Give Up on Doing What’s Right

Whether or not I have a chance to get outside or be around close friends, I at least try to avoid the things I might regret.  Somehow this is easy for me (I’ve never drunk-dialed), but I know that for others this is difficult.

By doing what’s right, that means I never say hurtful things, instead I over-communicate, and I blame myself whenever possible.  It means that I don’t always win, but at the end of the day I feel like I did what was best for the situation in the long-run, even if it wasn’t good for me in the moment.

This approach to being the better person led to one of the hardest weeks of my life, but now I know that I put everything in…so it’s possible to let go of the results.

If you’re not sure about something, write out what your instincts tell you.  Talk to a friend.  Sleep on it.  Sometimes it’s just a matter of letting time dull the situation for the right path to come to you.

–
These are the things that got me through the challenges in 2012.  I imagine that they’ll play a role in guiding me through the years to come.  I welcome any techniques you use to let go of the results and make it through the year.

* Wayne Willis not only helped me to let go of the results, he was a big part of knowing what path to forge.  I hope you too can find someone who’s been through similar life challenges and wound up on top.  Thank you, Wayne.

Flickr photo by sziliotti

2012 was a little bumpy, but I traveled far in the right direction.  When it was tough, I still went through the motions and pushed forward.

Looking Past the Happy Face.

There’s an unspoken rule among founders to put on your happy face and sing the pretty metrics.  We get good at spin. The reality is that startups take perseverance and sometimes you need to try the backup-to-the-backup plan. 

If you’re lucky, you’ll have a significant other who stays by your side and understands.  But that doesn’t always go as planned.  We get hurt; we hurt others.  Once again, we put on the happy face.  Relationships, too, take work, and the best we can do is to treat him or her how we’d hope to be treated, to stay open, and to stay honest.

If on Dec 31 the happy face feels tired, it’s tempting to feel like you’ve lost.  But a year is a long time, and looking back there was likely real progress and growth.  Needless to say, work and relationships were challenging for me in 2012, but when I look more closely… (and you should for your own year), I find so much to be proud of.

Stuff Gets Done

Skip this section if you’d like.  But I do need to write this stuff out…

AwayFind hasn’t "blown up" quite how I expected, but it has in other ways.  The product we have today is something I’m incredibly proud of.  And looking back, my gosh did we get a lot done in 2012:

• a new marketing site
• a recommendations system
• a better upgrade process
• an Exchange connectivity system
• parity between iPhone & Android
• NotifyMeNot.com
• MailPlane support
• an Outlook plugin
• an invitation system
• multiple calendar support
• a Chrome extension
• coverage on Fast Company, TechCrunch, NBC, Lifehacker, and so many more sites…

2012 was a solid year for AwayFind, and we may have even figured out That Revenue Thing.

And in my personal-professional world, I spoke in Santiago, Poznan, and Paris, presented a Tech Talk at Google, wrote articles for Lifehacker & Ars Technica, and grew so much as a CEO.

There was one area in my personal life that didn’t work out, but I’m proud to say that I was giving throughout and never hurt her unnecessarily.  I didn’t know I was capable of that, and though I wouldn’t wish the process on anyone, the best we can do is to be the person that we would hope we could be.  And that’s an accomplishment.  I hope next time (and there will be a next time) that I can give of myself in the same way.

Relationships may seem like a big part of the voyage, but there are so many destinations along the way, so many personal changes I’m proud of.  I’ve spent so much time this year in nature, I’ve got my mile time to 5:22, my waist to 31, I’ve gotten back into basketball, picked up chess, explored cities like Krakow and Valparaiso, deepened many friendships, and opened up to many new people.

Getting Through 365 Days

Of course there will be challenges and pain in a year.  Getting through them may feel nothing short of miserable, but when things get tough, that’s why you need certain things:

1. A system for taking care of yourself
2. The company of friends or family
3. Never giving up on doing what’s right

In the next few days, I’ve got a blog post coming that details these 3 things… please subscribe via RSS or email above.

As 2013 approaches, I’m a stronger person with a clearer head.  I have goals for next year that are attainable, and risks I’m ready to take…risks that just might turn into big rewards.   2012 may be behind me, but I’m proud of it, and ready for tomorrow.

Flickr photo by US Marine Corps

Have a safe holidays

The safe path is never to take chances, and my only regrets are from chances I didn’t take.

Don’t get me wrong, taking dangerous risks is not a winning formula.  But doing something uncomfortable or unorthodox that just might turn into something big, well now we’re talking.

I’m not a parent.  But I hope when I have kids that safety is not my first concern.  I want them to experience life, to take risks, and to make mistakes early.  I want them to know that opportunity is out there, but it doesn’t come easy.  Fortunately few risks are life-and-death.

From my work to health to how I treat people, I have my lines.  Driving fast? Ok.  Drugs? Not ok.  Risking my savings on my business? Ok.  Taking a 10 mile hike without water or a map?  Not ok.  Sharing a ride with someone I met 30 minutes ago? Most likely.

We all have brains in our head, and we need to take calculated risks.  I enjoy driving on mountain roads, putting everything into my company (while I’m young and single) and prefer to be trusting of new people.

What’s important is knowing ourselves, making careful decisions, and maintaining a thread of optimism.  I say optimize for living, not for safety.

Know your limits.  Be comfortable on the edge.  And have a fucking awesome holidays.

Flickr photo by epsos

Do you need others? Can you predict your future?

The following is an exercise of letting it out. Join me.

I am

I am curious.  I ask a lot of questions.  I don’t hold back when I have to something to say.

I am caring.  I take care of people.  I put others before me.

I am principled.  I stick to my beliefs.  I am predictable.

I am more theory than process.  I get the concepts intuitively, even the one that says that missing the process will hold me back.

Once upon a time

Once upon a time I grew outside of my work.  I danced competitively, ran marathons, shot portraits, practiced guitar, gave myself completely to another.

Once upon a time I could simply work harder.  If I simply finished the programming project or blog post I could be done.

Once upon a time I relied more on myself than on the others around me.  If I showed up alone, I had a chance for success.

Once upon a time I shared a lot with the world.  I wrote daily, I tweeted regularly, I carried a big camera.

I’m not

I’m not the one who studies the numbers and then tweaks the details.  I’m not going to wait until a good time to push Publish on this midnight article.

I’m not patient with others.  I’m even less patient with myself.

I’m not the kind of person who sticks to one system.  Yet I need to work within constraints to make progress.

I’m not sure what a single dimension of my life will look like in 6 months from now.  But I know it’ll be okay.

Like an offensive line that makes room for the star player to act, the right timezone frees you to make the play.

This past week I worked out of Paris (to attend and speak at Le Web).  I was reminded how incredibly easy it was to get ahead when everyone in the States was asleep.  But to keep my team on task and address some big opportunities, I also found myself Skyping and emailing from 1-3am.  It was the best and it was the worst.

A few years ago I worked out of Barcelona.  This past summer I worked out of Buenos Aires.  A big part of why I take these trips is that they’re simply better timezones for me.  And I mean it when I say that the only thing I truly dislike about San Francisco is Pacific Standard Time.

Timezones play a very important role in my ability to get things done.  Like a long flight without internet, they keep interruptions at bay.  But timezones also mean something psychologically—when I accomplish things before others are even online, it feels different.  A good timezone is an opportunity to not only get ahead but to feel ahead.  That’s powerful.

Try as I might to find another pattern, my routine has been unchanged for several years.  I get the most accomplished in the mornings, when I prefer to keep to myself.  I prefer to take meetings or calls in the afternoons.  And, no matter what advanced calendaring or ‘get up early’ techniques I’ve tried, nothing allows me to maintain this rhythm quite so well as a good timezone.

Essentially, I like to be slightly ahead of those I’m working with—ideally 3-6 hours.  In Buenos Aires I’m now 2 hours ahead of my east coast folks and 5 hours ahead of SF.  In Barcelona or Paris I was 6 hours ahead of the east coast (where I used to live), which was manageable…but the 9 hour difference from SF (where I now live) is not manageable.  So that means Europe is generally off my radar now, at least for long trips.

Of course, all of this assumes that when traveling there’s still an opportunity to get into a rhythm and complete your work.  Being far away from home can be challenging, but these days so long as you can find a good office, coworking space, or even coffeehouse, you should be able to get things done.  I try to take month-long trips since it’s enough time both to build a routine and qualify for monthly rates on apartments and offices.

I’ve been behind on writing to my blog, but now that I’m in Buenos Aires, it’s easier to find that time, as I’m probably writing this before you’re even awake.  I’m free from interruptions, and I must say that it’s nice to have long days in the summer sun.

Now it’s your turn to get away and get things done.  Who says they don’t go together?

I see now that with so many things, practice isn’t enough.  Don’t repeat my mistakes, which began 2 months ago.

Two months ago, I hired a writer (hi, Brian!).  We spoke the same language about business and saw eye-to-eye about how AwayFind can help people.  I was quite excited to work together.

Even more, Brian is not just a writer.  Brian is a 15 year direct marketing veteran, a thinker, and someone who more than deserves his Director of Marketing title.  But I’ve still never hired someone who I disagreed with so often and so thoroughly.

But he pushed.  So we tested and gathered feedback.  I was nearly universally wrong.

Now, Brian and I are different.  Different is fine.  But what was tough for me is that when I read some of his suggestions I thought, "No, that simply won’t work."  It wasn’t a "no, that’s not me" it was a flat out, "This won’t work, because of x, y, and z."

You see, my writing is no accident.  I can explain clearly why I chose one path or another, and why I strongly object to certain suggestions.

And yet I was wrong.  Consistently (okay, mostly consistently ; ).  With something I thought I understood.

I’m so glad for this experience (which is continuing, of course).  Even beyond its impact on my own writing, it helps me to see what our users, and people generally, value and appreciate.  And the bigger lesson here is not about writing: it’s that our assumptions about even our greatest perceived strengths may be wrong.

For a parallel—consider playing a musical instrument.  It takes both practice and technique.  One will certainly have to practice to attain proficiency…but without the proper technique it’s impossible to achieve the highest success.  We fundamentally understand this about music.

But in the rest of life we assume that enough practice will lead to success.  But technique is still hugely important.  We need to open up to the possibility that maybe our own technique—or at least our intuition–isn’t quite what we thought.

Consider your best strengths.  Then put your ego aside and really consider how differing approaches work, or be more objective in how you see its real impact.

When something so fundamentally different from your own (thought-out) perspective enters your world, perhaps you’re the one who needs to reconsider.

Flickr photo credit: JoelMontes

Remember when we had homework and tests?  It was tedious and difficult to get A’s.  But even without a report card, the best results require the same struggle.

I hated high school, but I recall my last two years idyllically: most days I arrived by 7:30, attended seven classes, ran competitively at the track, and then spent 3-hours in a nearby university’s computer science class.  And I did well, even if my moniker “dot com” was hardly offered with affection.

While I enjoyed the subjects, let’s be honest—few of us would’ve labored through so many chapters or worked out so many math problems if it wasn’t required.  The proof: the concept of “practice” is no longer in most of our vocabularies.

Nope, now we just do.  Do it right, do it wrong—business (or nearly all our activities) are about showing up and giving it a shot.  Mind you, I get to grade my team and I rarely let a B result out the door, but in this case it’s easier to be the teacher than the student.

As the teacher I have no trouble forgetting about the competition (as Seth Godin advises), but I still have to do my own work.  I can certainly show up and move things forward (“minimum viable CEO”?) , but the things that will make the most impact feel more like homework.

The difference between a B and an A+ may be 100 customers vs. a million.  Showing up is just lip service.  Pitching 50 journalists, writing 100 customers, creating another video…no one will ask me to do it, and no one will grade me if I don’t.

But it’s not just about work and making a startup succeed.  It’s the willingness to do something that’s seriously tough, even if the light at the end of the tunnel is far away and you may damage your ego in the process.

To be clear, I’m not talking about taking on more—no, ambition creep can be toxic.  I’m talking about taking the things that you’re reasonable/passable/or even good at, and bringing them to the next level.  (For me, that’s writing/marketing, and Spanish.)

As I approach my thirtieth year, I want to still be able to step up to the plate with the difficult things.  Not in response to someone asking me to, but because it’s the only way I’ll be happy with myself and will make a substantial impact before the next decade is up.

Growing up may be a struggle, but it’s also a myth.  We’re never grown up, and it’s never too late to take things to the next level.

It’s no secret our greatest asset is time and our greatest predictor of success how we spend it, yet most of us have grown into our roles and task lists without giving it much thought.

Where do we kick ass…and where do we struggle?  Where do we have leverage..and where are we a replaceable worker bee?

At a dinner the other night, we got on the topic of "what are you best at?"  An interesting question perhaps, but it led to a couple better, more specific ones:

• In what area are you uniquely skilled, relative to others?
• Of your unique skills, which can you leverage the most for impact?

Take two minutes to consider your answers.

Though there’s scarcely one right answer, it’s likely that your responses will not be how you spend most (or even much) of your time.

I believe my answer is my ability to offer feedback and communicate advice in a way that’s useful and specific.  With my team that comes in the form of product vision, specifications, and feedback.  With the outside world it comes in the form of speaking and writing.

And as I look back on the past decade, my only regret is that I haven’t written more, created more, and shared more.  Like many of you reading this, as my team and responsibilities have grown, I’ve dealt more with unplanned situations, rather than setting my own agenda.  But, as I wrote a few months back, that’s not the way to make a difference.

How about you — are you spending most of your day in an area where you kick ass and leverage your time?  Any advice, for you or for me, for how to get back on track?