Portrait of Sean Johnson

My name is Sean Johnson. I live in Chicago and lead product development at Brill Street + Company. I started an awesome outsourced web development company with three other guys in New York, and founded Jelly Chicago. I design, code, write, play basketball, cook, and read. My wife is much smarter than I am. I have a lot of character flaws. I'm working on it. I believe you're here for a reason, and I bet it's something pretty great.

During the last 6 months at Brill Street, I’ve had the opportunity to be involved in several dozen meetings with area VCs. I’ve also been able to work with my boss, who is a VC himself and has a very generous heart when it comes to sharing knowledge. Needless to say, it’s been a spectacular learning experience.

In the process, I’ve managed to cobble together a few early lessons that I’ll hopefully have the presence of mind to remember in the future. While certainly not rules, and most likely flawed due to a limited sample size and my own incompetence, I do think they might prove useful to start-ups looking to interact with venture capitalists on their own ventures. As with anything I say, your mileage may vary.

The most important thing is the team

I had heard this maxim frequently in the past, but had considered it hyperbole. It’s not.

Everyone has ideas for a company, and many of them are good. The idea, while important, is not the difference between success and failure. Execution of a mediocre idea is much better than a great idea poorly executed.

It takes a great team to execute on an idea successfully. VCs have learned that a smart, aggressive, flexible team of people can make things happen.

This is why they’ll often hire “entrepreneurs in residence” – someone who they think is talented and can make something happen, but who is between opportunities (most likely following a sale). They’ll pay this person to come into the office, listen to pitches, and think – and when the right opportunity comes up, they back them.

Simply put, they bet on the jockey and not the horse.

Which means when you’re thinking about your pitch, you need to seriously consider the caliber of your team, and if necessary make some upgrades or additions.

If your business is highly analytical and you lack a marketing whiz with expertise in running those kinds of campaigns, you’re in trouble. If you’re a tech company without a technologist, you’re in trouble. If you’re trying to sell an enterprise product and no one has experience dealing with the drawn out, convoluted enterprise sales cycle, you’re in trouble.

It’s also important to be honest with yourself – do you think that a VC would be comfortable putting money into a venture that has you at the helm? There’s a chance that the only thing standing between you and an investment is you.

If your venture could benefit from someone with more expertise or with a personality and disposition more suited to a CEO role, have the humility to find that person, make them a great offer and take on a role that is better suited to your skill set and personality.

The team matters more than anything else.

Listen, and be flexible

Most VCs are very smart people – most have been successful on their own prior to joining the firm, and they have had access to thousands of business plans and first-hand experience with dozens of startups just like yours.

Which means that when you’re pitching a firm, you should treat it as an opportunity to learn and not just a presentation. Most startups rarely end up doing what they originally set out to do, and the smart ones listen and adapt faster than the others.

During the course of your pitch you’re likely to get advice, often in the form of repeated questions around an area of weakness in your plan. Don’t bristle at this – learn to listen to it. It’s likely they’ve seen a similar company fail for precisely that reason. At the very least they’re pointing out the weakness in your pitch, which if corrected could lead to more success in future meetings.

It’s also important to listen during your pitch because they’re paying attention to you as much as they are to the deck. They want to see if you’re flexible. They want to see if you have logically thought through your ideas, and if not, how you react to weaknesses in logic being presented. They want to see that you can take advice without getting upset, since they’ll want to be able to do that as investors should they pull the trigger.

A mediocre business manned by someone who can listen and adapt will become better and can possibly become great. A good business manned by someone who’s inflexible and stubborn will probably never become more than what it already is.

Know your odds, and don’t take it personally

Many entrepreneurs I’ve talked to in the past about failed attempts at raising money had a chip on their shoulder, as though the VCs that turned them down were idiots or were doing it to spite them. In reality, these folks probably just didn’t have a solid grasp of the numbers. If they thought about it at all, they would probably have thoughts that the firm is choosing between them and, say, 10 other ideas.

The firms I’ve seen so far make only a few investments a year. So if you figure on any given day they’ve heard at least one pitch, and if you figure that of all the pitches they hear during the year they’ll make maybe three investments, you quickly see that the odds are not in your favor.

Which means that you should a) do everything you can to understand what those few investments tend to have in common, and b) not take it personally if a firm doesn’t choose your company for an investment. If you were putting several million dollars of capital into a company, you’d be picky as well.

Know your audience

Venture firms, and the partners who make the decisions within them, have certain industries or types of investments that they are drawn to. This could be based on their prior work experience, or a result of previous investments. But before you try to sit down with someone, it’s important to know what they’re investment preferences are – in many cases it’s not a stated purpose of the fund, but simply the personal preferences of the partners.

VCs like to have deep knowledge of the space. Lack of expertise in an area represents a risk – and with all the other things that could go wrong with an investment, it would be foolish to jump into a deal without sufficient knowledge or expertise. So don’t be shocked if a firm tells you that you have what sounds like a great idea, but that it doesn’t excite them – you could just be outside of their comfort zone.

Be likable

People prefer to work with people they like. If you have a great idea and a great team but are arrogant and abrasive, you’re probably going to have a difficult time raising money.

If a VC firm takes on an investment, they will probably take a board seat, and will be actively involved in the business offering advice, making introductions and trying to make the venture succeed. Which means they’ll be spending a lot of time with you. If you’re a jerk, they’ll probably think twice before entering into that kind of relationship.

So be friendly at all times – be humble, be gracious, be thankful that they’ve taken the time to sit down with you.

And remember that they all talk to each other, and that word can spread about your hot temper and derail your efforts at any other VCs you try to sit down with.

I’ve been fretting for the last few weeks about 2010.

Every year in December I take an inventory of the past year, and develop goals for the year ahead. Historically those goals have been relatively large, primarily focused on business or personal finances. And for the most part I’ve managed to hit them. I would argue that people who desire to do great things should simply set bigger goals for themselves. They’ll likely be surprised at how much they’re able to do.

But this year, three things have conspired to make the goal setting process unusually troublesome for me.

  1. The birth of Miles is of course the biggest factor – the last six weeks have been the best (and more tiring) of my life, and I fully anticipate that continuing into the next year. But infants can definitely put a cramp in your style, and when all that free time you used to be able to leverage completely evaporates, it makes it tough to think really big.
  2. Focusing on others has been an increasingly strong desire in the last few months. I don’t want to do things simply for myself like I usually do. I’d like to develop more of a heart for others.
  3. I’m learning that I desire the spotlight way too much. So much of my motivation is based on the desire for recognition – to do good work and (more importantly?) for people to know about it. Which, like many other things, might not be considered a bad thing to some people, but is something that I think needs remedying.

So perhaps for the first time, I’m actually finding myself writing goals that are smaller than the year previous. It might sound funny, but for years I’ve gravitated towards visible goals and shied away from things that are good and character building but ultimately small and hidden. And while there’s a place for the big and visible, maybe the small and hidden is where the really amazing stuff happens.

Small is the new big

Mother Theresa’s name gets thrown around so often (often with sarcasm or in jest) that it’s easy to overlook how unique her ideas were. Everyone knows she was a saint, but what most don’t realize is the manner in which she went about her ministry.

While most people are grasping for more power and visibility, she genuinely believed that the world is changed through the small and hidden. She regularly and consistently argued that the small things are where the action is.

There are no great things, only small things with great love.

Let us touch the dying, the poor, the lonely and the unwanted according to the graces we have received and let us not be ashamed or slow to do the humble work.

It is easy to love the people far away. It is not always easy to love those close to us. It is easier to give a cup of rice to relieve hunger than to relieve the loneliness and pain of someone unloved in our own home. Bring love into your home for this is where our love for each other must start.

It is not the magnitude of our actions but the amount of love that is put into them that matters.

We ourselves feel that what we are doing is just a drop in the ocean. But the ocean would be less because of that missing drop.

Jesus said love one another. He didn’t say love the whole world.

If you can’t feed a hundred people, then feed just one.

Be faithful in small things because it is in them that your strength lies.

Just 70 cents a day

When I was growing up, my parents adopted one of those foster kids you see on television – you know, the whole “70 cents a day can save a life” kind of thing. His name is Oscar, and he lives in La Paz, Bolivia. Other than sending them a check every month, your responsibility consists of optionally writing your foster child a letter once a year. The child does the same.

I never gave much thought to it – I don’t think I ever read one of the letters growing up. I did, however, make many jokes about how Sally Struthers was hoarding all this cash and eating caviar on her yacht off the Bolivian coast. I wasn’t even thoughtful enough to see whether or not Bolivia even had a coast.

Last year when I was home for the holidays, they received a letter from him with a photo, and I read it. It literally made me cry. Now a teenager, this boy’s entire life was changed because of my parents. He was able to go to school. He was able to afford clothing. He was able to eat healthy food. He was hoping to become a doctor. He was happy, healthy and excited about the future. And he loved my parents. He couldn’t stop talking about what a gift it was that these random people in America decided to sponsor him.

It was a small thing, writing a check for 20 bucks a month. But it transformed a life.

Small can change the world

If I’m honest, I think the reason I haven’t pursued doing “small things with great love” is that I’ve thought it was beneath me somehow. I’ve waited for years for some big, magnanimous, and public idea that I could do to “give back.” And while there’s nothing wrong with big things, my motivations have been much more about myself than about the cause.

Doing small things is hard, maybe even harder than big things. You don’t get the high of having a bunch of people congratulate you. In some cases, not a single person even knows what you’ve done. It requires humility, selflessness, patience and self-discipline. And there’s no big reward at the end of it. At least not an obvious one.

The Bible talks a lot about a concept of “The Kingdom of God”, and a common misconception is that it’s some vague thing that happens when you die. But in reality, the “Kingdom of God” is here, now. It’s about bringing God’s love here to earth, and that’s done primarily through small acts done with great love. Caring for the people who are ignored. Helping a neighbor who’s lost their job. Giving your extra coat to someone who needs it, a hot meal to someone who’s hungry. Loving everyone – even the people who others would consider “unlovable”. And doing so not because of what you get out of it, but because you want to create the kind of world that God wants, where people with the freedom to choose willingly decide to love each other more than themselves.

I’ve desired the big and showy for years, but this year I’m hoping I can think smaller.

It’s been a crazy year. A new home, a new job, a baby. For the last six weeks, the combination of lack of sleep, diapers and holiday insanity has rendered my brain mostly useless. With 2009 coming to a close, I feel a little bit of the fog lifting and am very much looking forward to an exciting 2010. But before turning the page, a few thoughts on what the last year has taught me.

The “risky” thing is rarely as risky as it seems.

Jumping from an established company with equity to take a pay cut at a job that is no sure thing might sound insane. And for a while, it did. But the last six months have taught me more than the last three years. I’ve met amazing, ridiculously talented people, have been trying to solve some very big problems, and have generally had a blast. Regardless of what happens in the next few years, I think the scary decision was the right one.

If you have the right partner, you’re 90% of the way there.

Most women would not have been keen on the idea of jumping ship for a startup 4 months before their first child is born. My wife is not one of those people. For the duration of our short marriage, she has been a constant source of encouragement. She believes in me more than I do. And even when I screw up, she helps me get up and try again. It’s hard to overstate how much of an impact the right woman can have on your life.

I learned how to let go of having to be in control of everything

I’ve watched as two extremely capable men have guided Morpho successfully during the last year with very little direct input from me. I’ve watched as Jelly has continued to grow and thrive in the hands of Jeff. I’ve watched how my last company has continued to plug right along after Matt and I left. And while I don’t think I’m any less valuable to a team, I have learned that life goes on without me, and that things can work amazingly well even if I don’t have my grubby hands involved.

Most importantly, I now know what everyone has been saying all these years about becoming a parent.

I know what it feels like to wake up in a cold sweat after a nightmare about your child. I know what it’s like to hear the smallest noise coming from the other side of the house. I know what it’s like to hold a little person for the first time like he’s made of glass.

I know what it’s like to have a dormant, cold heart ripped open. I know what it’s like to discover how selfish you are. I know what it’s like to go from 8 hours of sleep to 4 and not care. I know what it’s like to spend hours trying to come up goals for the next year and constantly thinking to yourself that having a happy, healthy boy is the only thing that matters.

I know what it’s like to admire your wife in a completely new way. I know what it’s like to be extremely grateful for your parents, for taking him when you need to take a walk, for cleaning the house when you don’t have the energy, for giving you encouraging advice yet keeping enough distance to help you figure things out on your own.

I know what it’s like to think about how your son will one day crawl and walk and pretend to be a superhero and go to school and get a bruised knee and fall in love and have his heart broken and go to college and have his views of the world changed and enter the real world and see his colleagues and friends lose heart and watch his grandparents die and walk down the aisle with a woman so beautiful it takes his breath away. And I know what it’s like to simultaneously want him to enjoy everything good in this world and keep him protected from anything bad.

He’s six weeks old, but it feels like he’s been here forever. And life is never going to be the same.

One of the more common complaints about one’s job is the inability to “get your ideas heard.” At every company I’ve been a part of, there was a large faction of people who lament over drinks about how they have good ideas, and the only thing keeping them from making those ideas a reality is their lack of power or clout in their company.

And they’re probably right, although not for the reasons they think.

The reasons they think their ideas aren’t heard have everything to do with the company. Their boss is trying to keep them down. The head of the company is too disconnected from the day-to-day to see a good idea for what it is. And everyone else is too lazy to implement it.

But in reality I think the problem is threefold, and all of it rests on the shoulders of the budding innovator.

Pooping your idea

The typical way in which these folks share their ideas is through what I call “pooping your idea” out there. Pooping your idea basically involves opening up Outlook, cc’ing a minimum of 10 people, outlining the basics of your idea, pressing send, and then patting yourself on the back, waiting expectantly for your boss or colleagues to tell you how brilliant you are. What usually ends up happening instead?

Nothing. The idea gets ignored, and ends up forgotten. The person who pooped the idea in the first place adopts an outlook that “no one listens to me” and decides to be an emotional drain on the company. If they aren’t going to listen to me, why should I work hard for them?

The two problems with most people’s approach to sharing ideas

  1. They Bite off bigger ideas than the organization is ready for them to take on.
    It’s not that the company isn’t interested in changing for the better, or doesn’t value innovation. In all likelihood, the company got to where it is because it learned at some point to do something better than most other companies. Rather, it’s that they don’t think that the employee is the person who can get it done. They’re trying to tackle problems that are out of their pay grade.
  2. They don’t do a thorough analysis of the problem. Instead, they take 10 minutes to write out their thoughts and send – no review, no evidence to back it up, no consensus of opinion, no massaging the argument and proposed solution until it’s just right. They seriously expect everyone else to figure that part out.
  3. They have no clue how to handle the internal politics involved in making something happen. The reality is that until you’ve earned a reputation as someone who can make things happen, very few people will listen to you. And even then, no one is going to take a memo you write and turn it into the reality you desperately want to see on their own. They’re busy – they have their own projects and problems they’re dealing with.

In short, since no one cares as much about your idea as you do, since you haven’t thought it out that well, and since no one trusts you to make it happen, your brilliant idea is immediately discarded.

The good news is that there’s a solution. And it’s easy to do. It costs nothing but your time. And it addresses all three problems above.

Microvation

Microvation is the principle of innovating on a smaller scale. While very few people in an organization have the power to make the kinds of decisions that can make or break a company, everyone can microvate in their respective areas of responsibility, no matter how small.

What does a microvation look like? Microvation is looking at a way to improve an expense report. It’s adding a “10% discount if you pay in 10 days” coupon to invoices. It’s building an extra 1-2% margin into a proposal and sending that amount back in the form of a check with a note about how you got the work done under budget. It’s setting up Salesforce or SugarCRM to handle client records. It’s creating a Basecamp account and training your colleagues on how to use it. It’s sending out a monthly email newsletter about your department’s progress on critical projects. It’s organizing a lunch and learn series, bringing in smart people in the industry to talk. It’s sending a Valentine’s Day or Thanksgiving card to your clients instead of the usual Christmas card.

By approaching your job through the lens of microvation, everything becomes an opportunity to practice the art of innovation (and more importantly, the art of execution.) By getting really good at small things, you earn the right to talk about larger things over time. It replaces cynicism about your job with excitement. Instead of pooping ideas, you take initiative. And instead of lamenting on what could have been, you get increasing responsibility as word spreads that you’re the person improves things and gets things done.

I would argue that by microvating, starting with the most insignificant project and working your way up, you can transform your job in a year. It was the exact process I followed when I moved to New York, in which I went from Account Manager to Director of User Experience to Creative Director in 12 months. It requires a lot of work, humility and patience. But the payoff in job satisfaction and professional growth is astounding.

A twelve month microvation plan

  • Months 1-2: Start with yourself. You want to start as small as possible, and the smallest organizational unit you can impact is yourself. So start thinking about how you can improve your efficiency. Think about improvements you can make to your own processes. Think about how to improve the look and feel of your desk. Think about ways you can become more organized at the office.

    During this period, focus most of your effort on the process of microvating. Focus on your analytical skills – have you defined the problem thoroughly, have you developed a mutually exclusive and collectively exhaustive list of potential sources of the problem? Have you brainstormed (for longer than you usually would) potential solutions? Have you analyzed thoroughly your strongest candidates? Have you received any second opinions?

    Also focus on execution. A great idea poorly executed is worthless. Learn how to define what success looks like, how to break the project into discrete action steps, and learn how to avoid procrastinating and get to work making things happen. At the end of two months, you’ll have made yourself considerably more effective and have developed the skills you’ll need later.

  • Months 3-9: Think about your department as your own small business. Once you get good at making things happen for yourself, you can turn your attention to your department. Again, focus on the smallest possible impact and work your way up.

    One effective way to spend this time is to think about your department like a small business, or professional service firm. Think about what its “product” is. Think about the way it markets and communicates that product to its “customer” (internal team members, actual customers, etc.) Think about how well it manages expenses and profitability. Think about the systems that are in place. Spend a day just brainstorming in each of these areas. You’re bound to come up with dozens of ideas that can have an impact on the company.

    Prioritize by the easiest to tackle first – you want to get some easy wins to build momentum. This means things that can be tackled with no money, limited time, and without anyone else’s assistance. Once you’ve knocked these off the list, you can start to address microvations that require small amounts of company investment or time, increasing slowly as you get better and start to build your reputation.

    During this phase, it’s important to focus on how you communicate and manage the politics of the organization. Learn how to build consensus, recruiting people to your cause one at a time. Learn how to organize work and manage others. Learn how to set expectations with people who hold you accountable, and develop a reputation for beating those expectations regularly.

  • Months 10-12: Step up to the plate With six months of projects under your belt, your boss is probably loving you at this point. Now is the time to attempt something a little larger. Again, you want to focus on something that is as small as possible, but is larger than just the confines of your department.

    Your boss is your most important ally in this, and it’s critical that you use all the skills you’ve learned in the preceding 9 months. You need to have an airtight analysis of the problem, the proposed solution, its benefits and drawbacks, etc. You need to have a concrete action plan in place. You need to arm your boss with what they need to go to bat for you effectively. And again, you need to build consensus one person at a time. Under no circumstances should you go into a meeting and try to sell a dozen people on an idea – it won’t happen. If you win them over individually, addressing their unique concerns and hitting the points they resonate with most, the likelihood you’ll get the chance to implement your idea will go up considerably.

    And when you get the green light? Go after it. Do whatever it takes to make it happen, ahead of schedule, under budget, and with your own special flourish.

    And then do it again. And again. And again.

    A year to a changed professional life

    The plan above might take more than 12 months. Not all of your projects will be successful. You might have superiors that genuinely don’t care, or do think you’re a threat. And you’ll probably get dirty looks from at least one peer who thinks you’re making them look bad.

    But if you spend a year doing what I’ve outlined above, your career will take a drastic turn for the better. You’ll earn the right to talk about big ideas. You’ll have the respect and admiration of your boss and most of your colleagues. And you’ll have acquired a skillset that will make you invaluable to any organization lucky enough to have you.

The servant leader is a unique and rare animal. Anyone who’s been blessed to work with a boss who demonstrates servant leadership knows what a dramatic impact it can have on employee morale and company performance.

Unfortunately, they’re hard to come by, partially because the traits that mark servant leadership are rarely what people identify as prototypical leadership characteristics. Young people aren’t taught about what it even means to be a servant in leadership or why it would be beneficial.

And, if we’re honest, the patterns of behavior that mark a servant leader are hard to do. It’s easy to act like one when you’re conscious of it, but when the pressure is on who you are naturally tends to come out. To practice servant leadership on a consistent basis requires a level of character, self-confidence and discipline that many of us simply haven’t developed.

What does a servant leader actually look like?

  • Servant leaders accept the role of leadership humbly – they approach it as something they’re called to do vs. something they have a right to do.
  • They spend considerable time focusing on building up their team, motivating them, coaching them, giving them the freedom to experiment and fail and grow and get better.
  • They will get their hands dirty when necessary – because they don’t approach their role as one of power or superiority, they are more than happy to pitch in and do whatever it takes to get the job done.
  • Their priorities tend follow this pattern: 1) Family, 2) Employees, 3) Customers, 4) Profits, 5) Self. (I would argue that for many leaders, the pattern they follow is exactly the opposite.)

How to tell if you’re a servant leader

Human beings are fantastic at self-deception, at convincing ourselves that we have more virtues and fewer flaws than are really there. And I bet if you asked 100 leaders, the majority of them would say they demonstrate the above traits on a regular basis. But is it true?

The best way I’ve heard to tell if you are genuinely a servant leader is to ask yourself the following question:

If someone came along who was legitimately better equipped to lead your organization than you were, and if you had the opportunity to bring that person into the fold, would you voluntarily share responsibility with them or step down and take on another role in the organization?

Just as the best way to test your attachment to money is to give it away, the best way to see if you approach leadership as a calling and not a right is to ask yourself if you’re willing to give it up.

For many leaders, if they’re honest, the answer to this question would be no. It certainly was for me when I first heard it, and I still grapple with it today.

What about you? If you knew that someone could take your organization to the next level if you were willing to get out of the way, would you do it? After making it to the leadership summit, would you have the humility to return to a role of followership if it were the right thing for the organization and the team?

Lots of people want to be leaders. A lot fewer people want to be followers. Being a follower isn’t sexy. No one will invite you to speak at a conference or write a book about how to be a good follower.

But followers help drive most organizations. A leader can’t be a leader unless they have followers.

Most people aren’t leaders or followers – they’re admirers.

Admirers sit on the sidelines. They do what they’re told, and they punch out at 5. They don’t think about how to make things better, just about how to avoid screwing up. They worry more about politics and who’s getting ahead, and don’t spend much time doing the hard work of making their company better.

Followers get their hands dirty – they co-create the future with the leader. They work with the leader to develop the strategy, to execute it, to see it made manifest in the world. And while they might not share in the public glory, they have the satisfaction that only comes from working hard and seeing it pay off.

If you choose to be a follower and not simply an admirer, you probably won’t make more money, won’t have a better title, might not have more responsibility – at least not at first. But what you will have is the opportunity to develop discipline, focus, problem solving.

If you choose, you can have more than a job – you can have an apprenticeship. You can embrace your role in creating your organization’s future, and use it as a training ground to create bold ideas and make them happen. And by making your boss look good, you earn their trust.

Someday in the future, when you’re a leader yourself, you’ll remember the days you spent following, and will be grateful you weren’t simply an admirer. And you’ll be extremely thankful for the followers that now work and stretch and achieve for you.

If you want to be a leader, learn to be a follower first. Admirers who become leaders are the folks people hate working for – the folks who steal ideas, hate giving credit, play games to get ahead. They might have the title and trappings of a leader, but they’re simply an admirer with a better suit.

Followers who become leaders are the people you love to work for – they’re creative, share responsibility, give their team opportunities to grow and learn, and love to see their people succeed.

Great followers make amazing leaders. Admirers just make more expensive admirers.

Most people think that they care about what they do – they want to do a good job, want to be a valuable member of the team. But I haven’t met a ton of people who I’d say want to be the best. Not the best in the world, mind you – simply the best version of themselves.

We wouldn’t admit this, of course. We’d say that we do our best all the time. Perhaps we even believe it. But I think it’s a lie.

Think about your last week at work. Of the 40 or 50 hours you spent working, what percentage of that time would you say consisted of you doing your absolute best? What percentage was you doing a “good enough” job? And what percentage, if you were honest, were you merely coasting?

How many meetings have you been in where your mind wandered, where you didn’t try to get the most out of it? How many assignments did you rush through to complete as quickly as possible? How many times did you cut corners?

If we were to look at my working lives honestly, the ugly truth would likely be that we spend far too little time investing ourselves fully in our work. If pressed, we could come up with excuses like “I don’t have the energy” or “they don’t pay me enough” or “it doesn’t really matter anyway – work to live”.

But if you’re someone who wants to not just survive but thrive during the recession, a sure-fire way to do so would be to invest yourself fully in what you’re doing. Simply put, to care more.

Care more

One of the most interesting things about programmers (and one of the reasons I’ve gravitated towards their circles in spite of not being a programmer myself) has been their pursuit of the craft. You can go out for drinks with programmers and be virtually certain that a debate will erupt at some point about the best way to solve a particular programming problem, or about the merits and demerits of certain languages or practices.

When you talk to many programmers, it’s not hard to get them excited about what they do. Their eyes light up as they talk, and they start throwing around words to describe code that might sound ridiculous to you – words like “pristine”, “beauty”, “elegance.”

How many people who work with you use language like that about their work? Do you? Why not?

The fact is, it takes the same amount of time to do something with passion as it does to do something without. It takes the same amount of time to create a beautiful report as an ugly one, the same amount of time to create a compelling presentation as a boring one, the same amount of time to contribute and take notes in a meeting as it does to space out.

And here’s the neat thing – it’s self-reinforcing. As you make the decision to care more about what you’re doing, you find yourself energized, and you find your work to actually be more interesting. Caring more begets caring more.

People who care more get noticed. People who care more get recommended. People who care more inspire others to do the same. And people who care more are rarely considered dispensable – because they’re so hard to find, most organizations would be nuts to eliminate your position, or to replace you with someone who’s dispassionate like everyone else.

So what would it look like to care more in your job? What would it look like for an account manager, or a salesperson, or someone in human resources? What would it look like as an intern? As a manager?

I bet that if you spent 15 minutes thinking about it you could come up with a clear, articulate picture of what your day would look like if you were fully present and engaged. And if you were to actually do it, I bet you’d get a lot more work done. I bet that the work you chose to do would be a reflection of your priorities and the priorities of the organization. I bet that work would be more inspired.

And I bet the people around you would notice.

Of all the decisions I’ve made in my life, by far the best one was to ask Michelle to marry me. While I’m sure I could have met someone else and been reasonably happy, there’s no way my life would have been the adventure it’s been in the five years since we met.

She pushes me, in a good way. Never through words – everything that comes out of her mouth is supportive and kind and loving. It’s through her actions – the way she writes down a list of things she needs to do and attacks it. The way she reviews and re-calibrates the direction her life is going on at least a monthly basis, making more time for the things that are most important to her. The way that she actually is eager to get up in the morning – the woman woke up at 6am on Labor Day because she was so excited to take a walk by the water when the sun was coming up.

While I have a skeptical streak in me, she overflows with possibility and joy. She very seriously believes that most things in this world are good – which many people say they believe but their lives suggest otherwise. She gets just as excited when she gets a good review at work as she does about me buying her Raisin Nut Bran from the grocery store.

I read once that if you were to write down the five people you spend the most time with and examine their lives, that’s your future. And to the degree that you want your future to be different, you might need to spend more time with different people.

Which, if it’s true, means that I could not have possibly done better at picking a spouse. The last five years have been one big attempt to be good enough for her – and I mean that in the best possible sense. Not good enough because she demands or expects it – she actually thinks I’m pretty swell already. But good enough because she deserves someone who is her equal, someone who makes her feel the way she makes me feel.

A tall task, but I’m eternally thankful that I get to try.

Happy anniversary sweetheart.

iPlotz – instant wireframing (Comments)

Consider this skeptic converted.

My new boss suggested that I use iPlotz for wireframing in my product development process. Being a pen and paper kind of guy, I was not too keen on the idea – I didn’t think I could iterate on ideas as quickly. But I told him I’d give it a shot.

While it’s not as fast as paper, it’s not that far off. You actually can crank through different concepts very quickly – the library of components at your disposal speeds up the process considerably, and their intentional decision to keep the screens low-fidelity saves me from the frustrating process of having to argue over details when you’re just looking for high level agreement.

The coolest thing though is the ability to use hotspots to make your wireframes interactive – effectively doing double duty and serving as a rough prototype to demonstrate functionality and flow through the site.

There are additional features for collaboration and project management, which I haven’t explored (considering I’m the only product/design guy on the team and the fact that Basecamp is pretty entrenched in the organization, not sure if I ever will.) I’m also using the Desktop client, and haven’t taken the time to explore the online version.

But the wireframing/prototyping feature set alone is enough for me to overcome my natural stubbornness and adjust my workflow to integrate this new tool. Definitely worth checking out.

My buddy David Kadavy called me out and asked me for my eight life hacks – the eight things that make me feel like I’m “cheating the system.” I usually ignore this kind of stuff, but this one was actually an interesting thought exercise.

  1. Read constantly.

    Pek beat me to it. But whenever colleagues, interns at the office or anyone else ask me what I do to get ahead, the first thing I say is to read. I was taught early on that people succeed or fail during their non-work times. While most people stop reading after school (or while still in school), people who get ahead are constantly seeking out new information.

    They say that creativity is nothing more than taking old ideas and combining them in new ways. In order to do that, you need a large supply of “old ideas” at your disposal.

    If you have an aversion to lugging around books, grab the Kindle (the device itself, or the iPhone app). I was able to tear through 14 books in 90 days after putting the Kindle app on my phone – the reading experience is fantastic, and it saves a ton of space. The only downside is you can’t share your books once you’ve read them.

    Reading also makes you more interesting at dinner parties.

  2. Show up an hour early.

    I mentioned this in my previous post on recession-proofing yourself, but it bears repeating. Early in the morning (or late at night) is a great time to tackle work without all distractions – the world is quiet, your mind is more calm and focused. You end up feeling energized for the rest of the day knowing you have a head start on everyone else.

  3. Get one important thing done each day.

    This came from Zen Habits, but has been super successful for me since I started doing it. I try to set one goal to accomplish each day that, no matter how effective or ineffective the rest of my days goes, would lead me to consider that day a successful one. It focuses your intention like a laser on the most important things, and helps you avoid being efficient but ineffective.

  4. Reframe everything.

    Every project you are given, no matter how small and inconsequential, is an opportunity to do something amazing. Starting in college, I got in the habit of spending time thinking about how to make a project better. A lot of the things I’m most proud of were simple projects that were transformed by asking this simple question at the outset, including:

    • Laying out every class report in InDesign or Illustrator, and often getting them printed at Kinkos.
    • Creating a stand-up comedy contest and a non-profit ad agency for my marketing student group.
    • Creating a custom website as my cover letter and resume to get my job in New York.
    • Making a series of wedding invitation “booklets”.
    • Buying jerseys and renting the high school field for a flag football game the morning of the wedding.

    It’s a self-reinforcing habit as well – by practicing on smaller things you’re more effectively able to reframe larger projects, and your tendency becomes to ask this instinctively at the beginning of something new.

  5. Unnetwork:

    A large percentage of my closest friendships these days started at networking functions, and I attribute that to the concept of unnetworking. I never go into an event expecting to grab a bunch of cards and shake a bunch of hands. Instead, I set the goal to meet one super interesting person, try to genuinely connect with them, and then become their friend. I almost never ask for things from them, I try to help them out whenever I can. The goal isn’t to get business from them, but to have a relationship with them, which has way more upside (although it’s often intangible).

    Of course, business opportunities often come up eventually, but they’re for the right reasons – because you have a mutual relationship based on trust and friendship, not elevator pitches and systematic follow-up.

  6. Have an inner circle.

    While I have a fair number of friends, I have a much smaller number of folks (as in 4) that I consider my inner circle. The most important criteria has been that they know and largely be in alignment with my values, and are willing to give me honest feedback and keep me accountable.

    Most people think I have a tendency to be too hard on myself. They think that my focus on character development and insistence on trying to become the “right” kind of person is misguided, or a waste of time. Aspiring to a certain standard and being willing to admit that you aren’t living up to it makes most people uncomfortable – they tell you to just be happy and live your life, and that everything is a process, and what’s important is to live in the moment and just… be.

    Which is fine if that’s your perspective, but it isn’t mine. Mine is that I have one life on this earth, that I have certain talents and abilities, and certain weaknesses and vices. And that all of this is for a reason and my job is to use all of that in the best way possible, according to a set of standards that are not ultimately defined by me.

    And in order for me to be successful on my path, I need people who are on the same page, and who are willing to push and be pushed, not who want to convince me that I’m wrong.

    Regardless of your beliefs about who you are, why you’re here and where you’re going, I’d argue an inner circle is vitally important. They help you maintain your sanity when things aren’t going well, they celebrate with you when things are going well, and they keep you focused on the right things. You only need a couple – it would actually be difficult to maintain that level of intimacy with more than a few people. But finding your inner circle is an exercise that’s very much worth the time.

  7. Keep a budget, and make your financial goals automatic.

    Three years ago, I returned from my honeymoon with nothing in savings and 8 credit cards that were maxed out. Today my wife and I have no credit card debt and save or invest 40% of what we make. And the secret to that transition was a Google Spreadsheet.

    We started keeping a monthly budget, accounting for every dollar that came and went from our accounts. Having a visual document that you both look at keeps you accountable and honest. And we quickly found that there was a direct correlation between how often we look at it and how diligent we are in implementing it. To this day, if we go a few days without looking at it we resort to our old habits. Which is fun, but ultimately destructive.

    It was important that we set gradual goals each month – cut back $50 here, $100 here. Doing it in increments instead of all at once allowed us to break our old habits and develop new ones.

    In order to knock out debt and accelerate savings, we set aggressive goals for both and made the transfers automatic. Once we took it out of our control, the system ran itself. Of course, every month following a big readjustment we’d screw up and overspend. We gave ourselves an “idiot fund” to accommodate this, and we allowed ourselves a lot of grace. We didn’t let the short term missteps get in the way of the longer term strategy, and that made a huge difference.

  8. Whenever you think something bad about someone else, never say it. Whenever you think something great about someone else, always say it.

    The seeds of discord are almost always sown with something trivial. You think something critical, sarcastic or downright mean about someone else, and you decide to say it. Because it feels good – there’s a bizarre joy in it.

    But once it’s out there, it’s in the world. It’s permanent. It causes a small cut in the fabric of a relationship. Enough cuts, and the fabric begins to fray, starts to come apart.

    I get in trouble sometimes for this one, but I believe it wholeheartedly. It staggers me how many people struggle to keep friendships, romances, or family ties together. Close friends of mine talk often of relationship troubles, wishing they could do something about it, but when I offer up this bit of advice, they often reply with “You and Michelle are different. It doesn’t work that way in normal couples.”

    But it can. My wife and I, if we’re honest, get that same temporary high from the sarcastic comment as anyone else. We make a conscious choice not to. Instead, our language with each other is constantly and unceasingly positive.

    Does this make us naive? I don’t think so – we both know that the other isn’t always happy with us. We both know that sometimes we do something stupid, or look silly. We both know that the other knows that guy or girl who just walked by is extremely attractive. But that doesn’t mean you have to say it.

    What everyone wonders, perpetually, is whether they’re good enough. Whether the other person thinks they’re valuable, lovable, beautiful, worthy of their time. Our entire lives are lived with this subtext – am I really worthy of someone’s love? Saying the nice thing every time you think it doesn’t remove this, but it definitely provides assurance. And there’s no downside.