40 things that made me who I am (for my 40th birthday)
Lessons from the mistakes and choices I've made that led me to being the happiest, healthiest, and most successful I've ever been.
Jason Lengstorf makes tv for developers with his friends
A Year of Steady Progress Is More Than I Expected
I never feel like I'm doing enough. But I looked at what I was doing a year ago and... it was kind of a shock how much changed. There's a lesson in here.
Stop Worrying About Engagement & Other Good Advice I Ignored
“Trying to go viral” is not a strategy. I learned that the hard way.
Your Job Doesn’t Matter (and That’s Great News)
I very much believe that none of this stuff matters. Our jobs, the work, all of it. It’s completely meaningless. I also believe this is a wonderful thing.
Constant, gentle pressure
How do you accomplish big things (and not end up too burned out to enjoy your success)? You need to apply constant, gentle pressure.
The Fastest Way to Grow is to Share Your Work
The keys to rapid growth are deliberate practice and continuous feedback. Small improvements add up fast.
Show Up & Do The Work
I used to believe ability was everything. I thought talent was the key to success. But I was wrong. Ability doesn't matter if you don't do the work.
Turn 1 piece of dev content into 10+ — use the buffalo stick
Learn how the best developer experience engineers multi-leverage ideas to turn one piece of content into 10+. This is THE secret to effective devrel.
Please stop multitasking. I’m begging you. Please.
The greatest trick we ever pulled on ourselves as knowledge workers was convincing ourselves we could juggle multiple projects with no consequences.
Be weird & fun (as a business strategy)
Every once in a while you get lucky enough to work on a project that taps into everything you love. I led one recently — and it goes live TODAY.
Output vs. Outcome
When you define work, do you focus on the output or the outcome? Learn what the difference is — and why it matters.
Please stop checking Slack and email during vacation.
Taking real, fully disconnected time off is good for your health and for your team. But you have to ACTUALLY disconnect to get the benefits.
The defaults matter
No matter what you’re building — habit, tool, or company culture — choosing the right defaults is critical. Learn how to use inertia to your advantage.
Intention vs. Drift
There are two ways to create. Either we intentionally make progress toward goals, or we drift & see what happens. For best results, I think we need both.
Don’t Be Nice. Be Kind.
“If you can’t say something nice, don’t say anything at all” is terrible advice that often backfires. Let’s find another way of looking at caring for people.
How to Draw a Map to a More Fulfilling Career
If we want a happy, fulfilling career, what should we focus on? Learn an exercise that’s helped me create clarity on where to focus my effort for success.
A career is a pie-eating contest & the prize for winning is more pie
They say “no good deed goes unpunished”. When we finish projects, it often leads to additional work. Whether or not that’s a good thing is up to us.
Convince your team to learn fast and try not to make a mess
People asked how to overcome objections from team members, management, & leadership when trying to adopt change. These ideas might help.
Yeet. Delete. Repeat.
We need to ship fast, learn fast — and do it all without burying ourselves in technical debt. Here's one way to set up your team for success.
Squishy vs. Load-Bearing Projects (or: How Not to Flatten Innovation)
Tackling projects with a team requires process, but too much process stifles innovation.
Creating Great Content Is a Process, Not a Project
The pressure to “get it right” when making content can be brutal. If we reframe content creation to be a process, it doesn’t have to be so rough.
How to Build a Consistent Content Creation Habit
If your goal is to be more consistent with content, your instinct may be to make a plan. But trying to plan your way to a creative habit is a mistake.
Draw the Box Smaller
If you’ve got big ideas and can’t seem to get people to buy in, it might not be your idea. You might just need to draw the box smaller.
Toolkits Over Checklists
Getting things done right is critical, but how you get things done matters. Learn why toolkits are a better approach than checklists when creating processes.
The problem with grinding
Are we successful because we grind? Or in spite of it? Learn how the grind might be holding you back instead of giving you the boost we might expect.
Get the results you want more often by reducing friction
How can we combine our knowledge of human behavior with critical thinking to give our customers, our teams, and ourselves the best chance for success?
2019 Personal Retrospective: Measuring progress and setting goals
Every year I write a personal retrospective to take a look at where I've been and set goals for where I want to go next — posted in public for the curious.
Planning vs. Execution: How much planning is too much?
How do we know we’ve planned enough? It’s impossible to plan perfectly, but a solid plan is still critical for getting things done.
What Are You Optimizing For?
The “right” or “wrong” decision depends on who you are. How can you be more sure you’re making the right decision for you? Know what you’re optimizing for!
First, Get Ready: What Mise En Place Teaches Us About... Everything
The best chefs rely on mise en place to guarantee every meal comes out right. It’s also a killer productivity hack. Here’s how you can start using it today.
The Ugly Other Half of Creativity
If we hope to turn our Big Ideas™ into meaningful progress, we need to become ruthless, murderous editors.
Personal Retrospective: Q1 2019
I set goals at the beginning of 2019. This is a check in to see how I’m doing, what I should keep up, and what I should change to make sure I get where I want to go.
The Importance of Setting Good Expectations
Every negative emotion I’ve felt (or caused) can be traced back to violated expectations. Learning to set better expectations is a superpower.
Yak Shaving: On Doing the Work Before the Work
Yak shaving, meta-work, and why they might just be the most important part of making meaningful progress.
Automation + Control: Progressive Disclosure of Complexity
How can we design systems that are friendly to beginners, but accessible to experts? There’s no one-size-fits-all solution — we need layers of abstraction.
2018 in Review: How I’m Structuring Goals to Make 2019 My Best Year Yet
Goals only matter if they’re measured. I’m learning from last year and setting measurable goals to make 2019 my best year yet.
Level Setting: Solve the Right Problem at the Right Time
If we want to solve problems effectively, we need to know which part of the problem to focus on at what time — and when to shift focus elsewhere.
Dirt Floors: How to Stop Putting Out Fires and Solve the Real Problem
What do dirt floors have to do with going to school? And what does any of that have to do with working more effectively?
Find the Why
Underneath the things we do, there are almost always deeper reasons. In order to make the best decisions and live the best life, we should figure out what they are.
2017 Retrospective
For many of us, 2017 was a pretty rough year. In this post, I’ll take a look at my 2017 experience, and how I’ll use that information to improve my 2018.
Make the Right Thing the Easy Thing: Better Choices by Default
Why is it — even though we KNOW what’s right — we often end up taking shortcuts and doing the wrong thing? Here’s how to be your best self, every time.
I spent 2 years living abroad in Airbnbs. Here’s what I learned.
In 2014, I claimed travel is not only possible, but cheaper, healthier, & more productive than living at home. 2 years & 13 countries later — was I right?
How I’m Looking at My Past to Improve My Future
We all look at the past sometimes and think about what went wrong. Here’s a simple exercise to make sure reflecting on our past is building a better future.
Only Keep Score Against Yourself
Success is not how much money you make. It’s not how much stuff you own. It’s not your job, your status, or your rank against the neighbors. So what is it?
Why you should never feel guilty about “wasting time”.
If you worry that trying new ideas might be “wasted time”, consider this: I lived in a van and wore eyeliner for two years — and I owe my career to it.
How to Have Great Ideas: Write Everything Down
If you’re waiting for inspiration, you’re doing it wrong. Great ideas don’t happen overnight — you have to make sure you give them a chance to grow.
Why do I always feel disappointed after I get something I want?
It’s tempting to always push for more. But does it actually make us happy when we get it? Why aren’t we happier after we achieve our goals?
Stop Glossing Over the Good Stuff: How to Be More Positive
We’re not born as “glass half full” or “glass half empty” people. We make that choice each day. Here’s how to stop negativity and start being more positive.
The Baseline: How to Create Long-Term Happiness
The quest for happiness is a rollercoaster of highs and lows. But can we build long-term happiness? I think it’s possible. Let me explain. With cupcakes.
Balance in Your First Year of Business
In your first year as an entrepreneur, it feels like you need to be running at 110%, all the time. But is that sustainable? Or necessary? Or even helpful?
Are you working in your “Goldilocks Zone”?
If you don’t get enough done? You feel like shit. Work too much? You feel like shit. How can you stay happy and avoid burnout? Find the Goldilocks Zone.
Why Can’t I Stay Consistent?
How can we make sure the things we care about most still get done, even when things get busy? Willpower isn’t enough; we need a routine to keep us on track.
Navigating the Tourist Trap
In which our hero grapples with his inner tourist and what that means to his outer hipster. Sort of. This is a story about self-loathing and sight-seeing.
Get More Done Faster: Scheduling for Maximum Productivity
Our jobs require us to work on many types of tasks across multiple styles of thinking. Here’s how to hack your schedule to get it all done faster.
Do More with Less: Drop Dead Physical & Psychological Weight
Getting rid of junk we don’t need is a sure way to feel happier. But this doesn’t stop at cleaning out closets; we need to declutter our identities, too.
Why We Work: Are We Just Working for Work’s Sake?
It’s easy to forget that we weren’t put on this planet to punch a clock. Do you remember why you work a job in the first place?
Remote Work Is a Win for Everyone
Did you know working in an office makes you less productive, less healthy, less happy, and even more likely to get divorced?
Measure on Results, Not Time Spent
When a company uses time to measure performance, employees are punished for high performance and rewarded for working inefficiently. This needs to stop.
Overtime: How to Lose Your Employees and Kill Your Business
The way many businesses approach pressing deadlines is terrifying. It’s also, ironically, one of the least effective ways to meet deadlines.
How to Know If You’ve Joined a Cult
Are our most valuable qualities being exploited at work to form bad habits that — if we don’t change soon — just might kill us?
Shitty First Draft
Starting a new project is scary. What if it’s not perfect? What if people judge you? Here’s how to jumpstart your productivity with a Shitty First Draft.
Leaving
Today I flew to Milan, Italy, to kick off a full year of living and working remotely. So how did I feel? I didn’t feel much of anything. Which worried me.
Wizards and Assholes
When someone asks you for guidance, do you help him out? Or do you condescend to him and make him feel like an idiot?
The Stories We Tell Ourselves
Everything we've ever done ultimately becomes a story. How can we make sure the stories we tell ourselves — and others — are good?
Do Men Have Best Friends?
I have a best friend. It feels awkward to say that out loud, and it really shouldn't. Why are men ashamed to have close relationships with other men?
Take Away Its Power
As a kid I was so scared of horror films I'd get scared just thinking about them. As I got older I learned to see how the movie ends to take away its power.
Take a Break
On Thursday I went a full day where I left my phone and computer at home. Would you believe me if I told you I was more productive than usual this week?
Your Taste Doesn’t Matter
Getting worked up because things that don’t affect me aren’t done my way is a shortcut to an extremely frustrating and deeply dissatisfying existence.
A Guide to Drinking for Adults
In my younger days, I had mixed feelings about going out for drinks. Lately, though, I love bellying up to the bar. Just not the way you do it.
It’s All Jazz
Every time I make a plan, it’s virtually guaranteed that something will go wrong. This was a significant stressor for me — until I learned to improvise.
See the Tree Coming
When you hit a tree, you can blame the tree, avoid the tree, or learn why you didn't see the tree in the first place.