Things that hold people back

Last week, we talked about Superpowers as special skills that propel people forward. This week, we’re going to be looking at the opposite — things that hold people back. So this week’s question is:

What’s one thing Jim is currently doing (or not doing) that you think is holding Jim back? Can you suggest one thing, however small, Jim might try in this area?

When I first started talking to people about Tinker, I told them that we’d focus on mainly on identifying and growing people’s strengths. From what I’ve seen, people are generally better off focusing on what they’re good at. Plus, working on strengths is usually fun and confidence-building. Happy times.

But a lot of people also asked me “what about the things that people aren’t as good at? Is that going to be part of Tinker too?” These people said that oftentimes the most useful feedback for them has also been the most challenging to hear.

This made sense to me. How effective (or ineffective) I am at a particular job is as much about superpowers as it is about things that hold me back. For example, one thing that has periodically held me back is conflict resolution. I run the gamut from being conflict-averse to conflict-prone, and there have been times where I’ve dragged my feet a bit on resolving conflicts. The reasons are for this are varied, but the outcome has generally been the same — we’ll hobble along for longer than we should, losing precious time and my credibility would take a hit. In these situations, the drag causes my superpowers not to shine as brightly.

We all have things that hold us back from being more effective at our jobs, from taking on greater responsibility, from the next promotion, etc. The first step to get over these is to figure out what these things are at the moment (these things can change over time). Once you have a handle on what they are, you’ll need to decide whether you want to work on them. You may, after all, be fine with where things are.

If you do choose to work on them, here are a few things to keep in mind:

  • You may never be great the stuff that holds you back, and that’s okay. It’s generally not a good idea to try to turn something that’s holding you back into a superpower. The better approach is to get them to a level where they’re no longer much of an issue. So maybe you’ll never be a 10 at writing, but if you only need to be a 5 for your job, then 5 is what you should shoot for. You may want to have an conversation with your manager and/or your team when it comes to this — “I’m never going to be great at X, so let’s talk about the minimum level you need.” Once you’re there, think about spend your time and energy working on other things, like one of your superpowers.
  • Consider getting someone (e.g., manager, mentor, coworker, etc.) to help you work on a skill that’s holding you back. These skill/activities can feel like eating peas (or beans or whatever vegetable you don’t like), so it often helps to have someone cheer you on and hold you accountable. Tell a coworker “I’m going to spend the next month working on X — can you check in with me every week to see how much progress I’ve made?”
  • If you find yourself working on something for an extended period of time and are not making much progress, by all means take a break. Focusing on something you’re not good at for an extended period of time can be demoralizing. Stop for a while and pick it up again later. Let people around you know that you’re taking a break.

When it comes answering this question about your teammates, remember:

  • This isn’t about what you think about them as a person, but about a specific thing that’s getting in their way. Focus on the action or behavior that’s causing the drag, not the person.
  • Consider following up with an in-person conversation to explore the what and why in a little more detail.
  • If you don’t have anything to say, don’t make something up. Either skip or refresh for another question.

Hopefully that helps. And please let me know if there is something in the above that rings particularly true for you or that you disagree with. Would love to hear your thoughts.


Further reading:

  • For an extended treatment of things that hold people back, check out this book: http://www.amazon.com/Habits-That-Hold-Good-People/dp/0385498500
  • There’s been a lot written lately about the downsides of strengths-based coaching, including:
    • https://hbr.org/ideacast/2016/01/stop-focusing-on-your-strengths.html
    • http://www.huffingtonpost.com/michelle-mcquaid/could-focusing-on-strengths-ruin-your-career_b_8985172.html
    • https://hbr.org/2016/01/strengths-based-coaching-can-actually-weaken-you

Superpowers that propel you forward

This week’s question: What is Sarah’s superpower (current or emerging)? How did Sarah use this superpower this week?

As a kid, Super Friends was one of my favorite cartoons. I used to get up early every Saturday morning so I could tune in and watch Superman, Batman, Wonder Woman and others use their superpowers to battle evil. Every Super Friend had their own set of powers and it was so cool to watch them use those powers.

This week’s question is meant to give people insight into their workplace superpowers. Superpowers are things that people do exceptionally well, often noticeably better than their peers. From what I’ve seen, these are the skills that help propel people forward. Is there something(s) that your manager or colleagues almost always seem turn to you for? Or activities you find yourself drawn to over and over again? If so, these may be your superpowers (or at least closely related). And they often coincide with things that people like doing naturally.

Maybe a superpower of yours is persuasion. Or maybe conflict resolution. Or data analysis. Or quickly developing prototypes. Superpowers can be anything. They can be general (e.g., great at sales) or specific (e.g., visually representing information). I wasn’t able to find a list of superpowers anywhere online, so I included some real-life examples below.

Even in roles that are typically considered “generalist”, superpowers can be important. They differentiate you from other people in similar roles. For example, Product Managers need to be competent in a wide range of skills. But every stellar Product Manager I’ve known has also been exceptional at a smaller number of things. Some have been really good at understanding user needs. Others have been skilled at advocating for their product/team. Similarly, a design manager once told me that when hiring designers, he looks for someone “who has strong all-around design skills so they can be helpful on a variety of projects, but also a superpower in visual design, interaction design, or another specific design-related skill.”

If you don’t think you have a superpower, or don’t know what it is, don’t worry. Sometimes they take a while to find or figure out. Input from others can help you figure out what yours are — that’s why we have this question as part of Tinker. And you may need to seek input from a broad range of people (e.g., not just work people). Most people I know have at least one superpower or even number of them (say 2-5).

Once you’ve identified your superpowers, what’s next? Figure out how to use and grow the superpower for the benefit of you and the world of course!

  • Seek out roles and environments that make the most of your superpowers. How useful a superpower is depends on the context. I once worked with an individual whose superpower was storytelling, but there was little use for that skill in his job. The more overlap there is between your day-to-day work and your superpowers, more your superpowers can help propel you.
  • Find mentors to help you hone these skills. The good thing about developing your superpowers is that you’re likely to work on them of your own volition. But additional guidance and feedback can be very, very helpful. Find someone (e.g., your manager, someone else who’s really good at the skill) and ask them “I’m interested in developing X skill. What are some things that I can do make me even better at X?”. Try to work together on a project, or have them give you feedback on your work.

Superpowers are like rocket fuel. And people generally enjoy using their superpowers, so it doesn’t feel much like work. Next, we’ll talk about something that’s a little less fun — things that hold people back.

Until then, have fun exploring your superpowers!

Note: This week’s question asks you to identify your coworkers’ superpowers. It’s possible that you’re not able to (e.g., you haven’t worked closely enough with them, you haven’t seen them in situations that would bring out their superpowers). That’s okay — just say so, and maybe let them know that you’d like to see them in more situations that bring out their best.


Examples of Superpowers

Here are a few examples of superpowers of people I know:

Terry is really good at bringing in concepts from different disciplines and applying them to problems. He’ll often take facts and case studies from seemingly unrelated areas (e.g. applying the Oregon Experiment, a book on architectural planning, to the restructuring of an engineering organization). When he does this, it helps people see problems in a different light which often leads to solutions that we hadn’t seen before.

I’m (Howie) really good at visually representing information. I enjoy taking information of all kinds and laying the information out visually. These could be graphs, tables, diagrams, mind-maps, slides (I hate to admit it, but Powerpoint just made sense to me), etc. People I work with often find these visuals useful. How do I know? They’ll often ask me for them.

Andrea is really good at developing ideas. One of my favorite phrases she uses is “this is a mediocre idea on the way to a great idea.” She’s really good at taking an idea and then exploring it from different angles and perspectives. She understands that brilliance often comes from a process — starting with something that’s a bit rough and then continually molding it until someone much better emerges. She has the patience to work through this process and will often entertain possibilities that others won’t.

Want more? Check out:

This week’s Freakonomics Podcast, “How to Become Great at Just About Anything“, is cool.

http://www.inc.com/matt-ehrlichman/finding-your-career-superpower-3-questions-to-ask-yourself.html

https://hbr.org/2009/05/why-you-should-encourage-weakn.html

http://strengths.gallup.com/default.aspx

hiring for the future

Assume that you are hiring people who will stay with your organization for at least five years. In that case, it’s more important to think about where they will be in their second year, after one year of practicing and coaching, versus where they enter in year one… Building an organization around practice means hiring people who are responsive to it: people who like an duse feedback, who enjoy working with a team, who are comfortable talking about their mistakes, and who are eager to improve. Consider the skills that are required for your profession but that are not susceptible to improvement through practice. Hire for these skills.

From Practice Perfect by Doug Lemov, Erica Woolway, & Katie Yezzi

Rethinking rituals for a new workforce

Yesterday, I came across this article on the economic and political impact of job automation on FiveThirtyEight. Their analysis was done by looking at the percentage of non-“routine” jobs, under the theory that those jobs are most at-risk for automation. It mentioned that these jobs accounted for all job growth in the United States since 2000, with the Bay Area, where I live, occupying two out of the top three metropolitan areas in smallest share of routine jobs, largest job growth, and largest average wage growth.

Let’s focus on the the discussion of “non-routine jobs.” Given that job growth is pretty much only in this sector, it is just another term for what is a clear change in the workforce of America. Consider that in 2002, sociologist Richard Florida referred to “no collar workers in his book, The Rise of the Creative Class—a distinction he drew up between the dress code of creatives from the blue collar and white collar workers of the previous generations. In 2006, business writer Daniel H Pink said that these new jobs were either “high-concept” or “high-touch” requiring right-brained thinking.

Notice the similarity in non-routine work of a no-collar worker that is either high-concept or high-touch doing work that is not-automateable because it requires right-brained, creative thinking. Ignoring the social and political implications, the reality is that this is a different workforce than the generations that preceded it.

And yet, the rituals that surround that work are firmly grounded in the past.

Our grandparents had their blue-collar wages negotiated under collective bargaining. Our parents had their white-collar salaries determined by performance reviews that were later modernized into 360 degree feedback. What do we have in our no-collar jobs?

As an engineering director with thirty direct reports in my final year at a top 10 internet company, I had to do 360-degree annual review. It was the most tedious part of being a manager and one of the most dreaded thing among my people. Doing a good job with it felt like a constant fight against the natural order of what motivated and inspired my engineers.

And yet, the cutting-edge job performance idea is taking that same process and increasing its frequency and adding big data-esque quantitative metrics. They believe that if you take incentives designed for a non-creative work, automate its application to evaluate non-automateable jobs, have them suffer this dread on a routine basis instead of once a year, and apply arbitrary qualitatively evaluations of right-brained, non-routine, high-concept/high-touch work that this will magically inspire these non-collar wearing creatives to perform better, and not the opposite.

That’s some serious wrong-thinking.

Useless employee ratings

The court filing said that managers were forced to give poor rankings to a certain percentage of their team, regardless of actual performance. Ratings given by front-line managers were arbitrarily changed by higher-level executives who often had no direct knowledge of the employee’s work. And employees were never told their exact rating and had no effective avenue of appeal.

From the New York Times

How to become a better product manager

The importance of practice in a role that’s measured mostly by luck

(Originally posted on Medium)

This is not going to be a skill vs. luck essay. That topic warrants its own post. For now, let’s say product management is one of those fields where both skill and luck play a role in determining how successful you are. Luck may even play a dominant role. But you can’t really control luck, so let’s talk about skill. My hypothesis is that a methodical approach to skill development is main thing keeping most PMs from being great.

Why is skill development hard for PMs? In my view, the job itself isn’t set up for systematic skill development. The nature of the role lends itself to a somewhat random learn-as-you go. PMs are constantly jumping between different and disparate activities (e.g., backlog priorization, management presentations, working sessions, data analysis, etc.) and this makes it hard to hone in on certain skills for systematic development. Compare this to salespeople who can practice their pitch multiple times on different customers, designers who are constantly revising and improving their designs, and engineers who often budget time to refactor their code. As a Product Manager, most things happen just once. Once you prioritize a backlog, you’re not going to go back and prioritize it again. It wouldn’t make sense to do a “practice prioritization” the way a salesperson can practice a pitch. So how does a PM actually become a better PM? I think the principles of deliberate practice can help.

Deliberate Practice

By now, most people are familiar with the 10,000 hour rule. Simply put, it’s the notion that across a wide range of fields (e.g., sports, music, chess, medicine, etc.), it takes 10,000 hours of deliberate practice to reach expert levels of performance. This rule, however, is widely misunderstood. Most people focus on the “10,000 hours” part, and miss another important phrase — “deliberate practice.” Not just practice, deliberate practice.

The current research on development of expertise suggests the top experts in many fields practice their craft differently than the rest. Hard work is required, but in competitive fields, everyone works hard. In addition to putting in the hours, it’s also how the hours are used that separates the true experts from those who are just very good.

Chris Rock’s funny doesn’t just happen. Wikimedia Commons

 

What exactly is deliberate practice? There are many examples scattered across the web and in the literature, but one of my favorite examples is Chris Rock and how he prepares his comedy routine. The Chris Rock most of us see is the brash yet polished comedian performing in front of thousands. What we don’t see is the months of painstaking work that goes into producing the 90 minutes of material he uses in his performances. To prepare this amount of material, Rock will frequent a small local comedy club in New Jersey 40 to 50 times. Each time, he tries some new material and takes copious notes on the audience’s reaction. He uses the reactions to rework his material over and over again until the content and delivery are what we expect from the best in the world. My guess is that many professional comedians put in the hours, but few are as methodical as Chris Rock.

So let’s break it down — what makes Chris Rock’s method of preparation a form of deliberate practice instead of just practice? Deliberate practice is a complex subject (see this, this, this, and this), but here are the slightly-adapted components that I think are relevant to product management:

  1. Design: the practice activity must stretch the individual just beyond his current skill level. Stretching too far may actually slow down skill development while stretching too little doesn’t do much. If done right, the activity should cause strain or discomfort. The design of the activity is often done with the help of a coach.
  2. Feedback: there must be immediate feedback as to whether the individual accomplished the stated goal of the activity.
  3. Repetition: the individual must repeat the activity again until it’s done right.

In Chris Rock’s case, his New Jersey club sessions are designed to test new material, constantly stretching his creative boundaries (apparently, trying a new joke in front of even a small group of people is extremely uncomfortable, even for professional comedians). He gets the feedback immediately from the audience reaction. And he repeats this over and over again until he has his 90 minutes of material.

Deliberate practice isn’t fun. That comes later (for Chris Rock, it’s the actual performance). This type of practice is hard, grueling work. The good news, though, is that many of us have done this type of work at some point in our lives, even if it’s for a short amount of time (e.g., playing sports, learning a musical instrument, even learning how to drive has elements of deliberate practice). But few people have figured out how to apply this type of practice to the workplace.

The Problem: Applying Deliberate Practice to Product Management

The use of deliberate practice as a way to increase performance has emerged more quickly in some fields than others. Sports is one where deliberate practice has taken hold among the top performers: Kobe Bryant, Michael Jordan, and Tiger Woods are all examples of elite athletes whose practice habits mirror the core tenants of deliberate practice. The benefits of deliberate practice have been shown in chess, music, teaching and medicine.

How can you get good at so many instruments?! Wikimedia Commons

But deliberate practice doesn’t seem to have taken hold among product managers. In fact, it’s hard to find much material on its use in business and technology. It’s easy to see how deliberate practice can apply to areas like sports and chess where you do the same (or at least very similar) thing over and over again. But how do you apply deliberate practice to product management, where, as I mentioned before, every day is different from the last? Product management simply doesn’t have the repeatable tasks that you find in chess, music, sports, or writing.

Also, a good PM needs to be competent at a wide range of skills. So even if you could find time to practice, it would be nearly impossible to do so across that many skills. And what about the feedback? Sometimes, there’s quick feedback (e.g. running an A/B test). But other times, like when we’re trying to influence user behavior, we won’t know whether a product is successful until months later. These confounds aren’t unique to product. I actually think that they’re more the rule than the exception in today’s working environment.

Possible Solutions

I haven’t tried these in the field yet, but I wanted to get these ideas out there so people can start experimenting. The key in each case is to isolate a specific component of the skill, find ways to incorporate deliberate practice elements while at the same time integrating the activity into the mainline work of a PM as much possible.

Strategy

In my experience, Strategy and Narrative are deeply intertwined, so a good place to look for ideas regarding how to develop strategy skills is writing. In a way, professional writing is built around deliberate practice: write → get feedback on draft → repeat.

So here’s an idea. Commit to writing six strategy documents, one per month. Each strategy doc should be 2–3 pages. They should be in long-form text. Diagrams and charts are okay, but No Powerpoint. Ask at least 3 people you respect to read these documents and give you feedback. Ask them to focus on 1) whether the strategy is sound and why, and 2) whether the writing is logical, coherent, supported, cogent, etc. (let the grammar and spelling slide). Document their feedback. These strategy pieces don’t need to be company-level Big Kahuna strategies. It might be easier to start with something narrower like “Product Strategy for User Segment X”. But be clear about the objective, write the piece, get the feedback, and incorporate it into your next piece.

Prioritization

If there’s one thing a product manager should be able to do, it’s prioritize a list of options with sound rationale. PMs get plenty of practice doing this — if you’re doing your job right, you should be prioritizing things all day, every day. But how do you turn this into deliberate practice?

A annotated page out of Alexander Graham Bell’s lab book. Wikimedia Commons

One way is to take a page out of science labs and document [pun intended]. Since all PMs love spreadsheets, I’ve created this spreadsheet as a starting point for how PMs might document their everyday prioritization decisions. For every decision you make as a PM, this ledger allows you to to track the decision, the measure of success, and whether you were right. This gives an ongoing tally of # of rights vs. # of wrongs so you can do fun things like track your moving percentage of “rights” over time.

But more importantly, this approach does two specific things:

  1. You should start to uncover your own biases when it comes to decision-making — where you tend to be right, where you tend to be wrong, and why. Maybe you tend to overestimate users’s willingness to try new things. Or maybe you tend to underestimate the impact of some design heuristic.
  2. Much like the lab notebook, you can use this ledger as a tool to uncover deeper insights into your users and your market. These insights could lead to new product ideas new product ideas or even an idea for a new business. Many PMs I’ve worked with already have some way of doing this, but often without the diligence that could lead to sustained improvement and insight.

Also find someone to do this with, such as your manager or someone on your development team. Having a partner can help keep you honest. Even the best of us explain away situations when we’re wrong. And if you fight the right partner, it can be fun — thinking of it as hacking decision-making.

Communication (verbal)

I’ll borrow one of the methods that Doug Lemov uses with training teachers at Uncommon Schools, a charter school that puts heavy emphasis on developing the best teachers. In his book Practice Perfect, Lemov describes how he uses role-play as a way to have teacher practice how they handle different classroom scenarios such as unexpected comments from students. Lemov will get a group of teachers together and have one play the role of “teacher” while the others play the “students.” The “teacher” will go through the lesson verbatim and the “students” will throw out unexpected questions, answers, etc. The teacher is expected to respond exactly as he would in class. If the teacher stumbles, Lemov (the coach) stops, identifies the mistake, offers suggestions for improvement, and rewinds immediately for the teacher to try again.

Before your next important presentation, ask a few people to get together to role play. Budget 2–3x the expected length of the actual presentation for practice.

When you role-play, remember the following:

  1. Say the actual words. I’ve been in countless prep sessions where people (me included) walk through the slides and say something like “on this slide, I’ll talk about this, on this slide I’ll talk about that.” Use the actual words you would use on game day.
  2. Designate someone a coach. This person should be charged with identifying strengths and weaknesses, and rewinding the tape.
  3. Repeat.

Practicing like this is admittedly contrived. But many practice activities are. As Lemov notes, these exercises intentionally distort reality to enable us to work on specific areas. Keep the goal in mind: you’re isolating a skill (communicating the content) and practicing it so that when you actually give the presentation, you can focus more on the higher-level stuff, like connecting with and influencing people.

Analysis

The best way to develop these quant skills is to work in an area that generates lots of data with short feedback cycles (Short = daily, if not more frequently. Weekly is acceptable, but nothing longer). These are typically in optimization areas (e.g., landing page, sign up, shopping cart, “growth hacking”). These areas usually aren’t the sexiest, but it might be worth spending 3-6 months in a role where all you’re trying to do is to get the conversion on page X up by a few percentage points. Similar to the prioritization exercise above, document what you tried. Work with a strong data analyst that can help you interpret the data (e.g., discuss sample sizes, sources of bias, 1st order vs. 2nd order effects, etc.). The very nature of this type of work lends itself to deliberate practice, as long as you’re intentional in your approach (design, feedback, repeat).

If you can’t find this type of opportunity, you can still work on your analysis skills (I’m assuming that you’re already incorporating regular quantitative analysis in your job — if you don’t, you need to). If your company is anything like the ones that I’ve worked at, you’ll get plenty of feedback anytime you present data. That feedback is usually helpful, so pay attention to it. But oftentimes it is unstructured and/or hit-or-miss. What’s even more helpful is systematic feedback from someone who really understands how to work with data. Find a data scientist and ask her to get together with you every other week to critique a piece of analysis you did. Then take her suggestions,rerun the analysis, and see what you find. Keep a log of the feedback and try to incorporate the feedback into your next piece of analysis. You’re doing the analysis anyway, so this is just one more step.

If you’re doing these activities right, you shouldn’t be fun. Writing long-form text is hard, logging each prioritization decision is mind-numbing, practicing a presentation with the actual words is uncomfortable and weird, and optimization work is grinding. But that’s the nature of deliberate practice. These activities should be pushing you in ways that cause discomfort.

So if I do the above exercises for 10k hours, I’ll become an expert PM?

Not likely. Product Management as a whole isn’t a field where deliberate practice alone can bring people to expert levels. It lacks some of the important characteristics of fields where deliberate practice over a long period of time can bring people to a very high level of expertise. In product, you have to search to find repeatable tasks. The relationship between cause and effect is oftentimes unclear. And while some PM skills are closely related (e.g., analysis and prioritization/decision-making), others may be largely unrelated (e.g., analysis and communication). There’s the role of luck and other things outside a PM’s control. And it’s simply impractical to expect that any PM is going to spend 10k practicing — we have product to ship after all. So it’s unlikely that deliberate practice alone will lead anyone to levels of PM nirvana.

But the principles of deliberate practice can certainly be helpful in developing specific skills, ones that can accelerate growth as a PM. Doing so will take time and energy. While the notion of this type of practice can be a bit daunting, getting started doesn’t have to be. In fact, Cal Newport (who I mentioned in the above comment) hypothesizes that with the right deliberate practice, you should be able to see a separation from your peers at well under 10,000 hours, perhaps even starting at few hundred. I think this is likely to be true in product management since since very few product managers actually engage in deliberate practice. While it’s unlikely that you’ll notice an immediate difference, my guess is that you’ll start seeing a change sooner than you think if you keep at it.

But remember, your skills exist to serve the product

Remember that all of this should be done with the end goal of building great products. Just as Chris Rock’s small-club sessions ultimately serve to improve his big performances, your skills as a product manager should ultimately result in products that delight your users (vs. building skills for the sake of building skills). Deliberate practice has pushed the boundaries of what is possible in many fields and I’m curious to see what it can do for product.

Work Life

This is a blog about work life.

As a kid in the 80’s, futurologists predicted a coming generational war between baby boomers hitting retirement and my generation (Gen X) and the next (Millenials). This war would be a series of escalating battles fought on the ballot box over the removal of depression-era social contracts such as Social Security.

And yet baby boomers have been hitting the traditional age of retirement for half a decade now and it hasn’t happened yet.

Ignoring the obvious absurdity of a generation of “slackers” and “hipsters” combining forces to wage war against our own parents, the need was nullified because previous generations delayed retirement and work in retirement while our generation redefines success in work to be more than a race for economic rewards.

We went to war, not with each other, but with the traditional meaning of success and failure, of reward and punishment, of life and work.

If we were to extrapolate this to generational theory it is not in the rightness of each generational archetype1, but in the wrongness of fundamental assumptions we’ve previously all bought in to.

This wrongness is no more evident evident in “work life.”

When people think of “work life” they have of one of two images.

The first is someone whose life is work. This person throws everything into work and has no identity outside it whether that is the type A heart-attack-inducing executive of the Lost generation, the Boomer yuppie lawyer or doctor, the libertarian Gen-X English major turned hedge fund manager, or the student-debt-ridden, marriage-delaying hipster sleeping under their office desk. The assumption here is Koyaanisqatsi, life out of balance. That person is so enamored with wealth and success that they give up their health, joy, values, and family for it.

The second is the term “work-life balance.” The assumption here is that work and life are opposites: work is something to be suffered through and success must be sacrificed in order to have just enough material things to sustain a “life” away from work.

When we say “the wrongness of fundamental assumptions in work life” we challenge those assumptions above in order to redefine what work life is.

To challenge the first assumption, is it so hard to imagine us working in a manner that improves our health, brings us joy, speaks to our values, and extends our social family to include the team members we work with? To challenge the second assumption, can’t we do work that we find fulfilling because it allows us to be proactive, it challenges us, and it gives us a sense of purpose?

A year ago, I quit my job as director of engineering at a top 5 internet website. In the traditional assumptions, given that I’m a long way from retirement age, it must be because I either made tons of money, was pushed out, was deeply unhappy, or burned out.

But none of those are true. The company I was working at was a non-profit where I took a $50k salary cut versus competing offers to work there. I stayed for three more months than intended because the leadership there asked me to. I had enough fun in my job write my resignation letter in pirate-speak and share it on Talk Like a Pirate Day to the company, community, and world. Finally, having spent those years as a manager, I spent this year having fun programming again.

I was going through a transition where some time away from a job was what I needed. And like all times in the wilderness, long before Walden, I didn’t leave because I had the answers, I left because the only answer I had was that I didn’t have the answers.

Here is what I learned in the wilderness:

I believe we can have a work life. I believe that this means that work should be a part of a healthy life. I believe that work should bring us joy. I believe we should do work that speaks to our values. I believe that my social network and those I work with are not firewalled from each other. I believe a good work life should empower us, it should challenge us, and it should give us a sense of purpose.

Unfortunately, that’s all I was able to discover in my time in the wilderness. I don’t have the answers beyond the belief that all the above are possible in a work and life. I don’t have a prescription.

We don’t know what’s right but we do know what’s a wrong work life and we are embarking on a journey of discovery to the a right work life. But that’s why we tinker: we try, we succeed, we fail. That journey will be work, but we want to approach this journey the the same empowerment, challenge, purpose and joy that we expect to have when we get to the destination. This blog is our thoughts on that journey.

If that speaks to you values, then why not be part of this conversation? Participate on this blog and tell us your ideas and experiences in your journey of discovery, or share it with me via e-mail: tychay+tinker@gmail.com.


  1. Lost Generation: the adaptive artist; Baby Boomers: the idealist; Gen X: the reactive nomad; Millenials: the civic hero.