Jason Lengstorf

I’ve written 45 posts about how I stopped being such a dingus.

I've made a ton of mistakes, learned a lot of lessons, and — in a few fortunate cases — figured out techniques that make my life more pleasant and fulfilling. I'll never tell you how to live your life, but I wrote down a little bit of how I live mine.

Stop Worrying About Engagement & Other Good Advice I Ignored

“Trying to go viral” is not a strategy. I learned that the hard way. Here’s how I screwed up early on, and what I do now that works.

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.

Checking Slack and email during vacation is bad for you AND your team. Please stop doing it.

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.

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. Learn how to avoid stagnation with adaptive processes.

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 business 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: Uncovering the (Sometimes Hidden) Reasons We Do the Things We Do

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: What went right? What could have gone better? How will I improve going forward?

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.

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.

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.

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.