Skip to content

🥲 Letter 59: Failure, Getting Fired, Goals, Gasoline...

8 min

Which screw ups are on your failure résumé?

Hello fellow learn-it-all,

Greetings from Chicago 👋

On one of my walks, I couldn’t help but laugh at this log below. Talk about a turtle part-ay!

From what I know about Darwin’s theory on the survival of the fittest, it looks to me like a predator might come to town because this log is a bit over populated with these reptilian friends.

If you are new here or missed last week's edition, you can catch up on the past letters here. If you are reading this for the first time, I’d love you to sign up below to join the other learn-it-alls:

Now, what's in store for this issue?

  1. A reflection on the past trimester of 2021
  2. A speech by the legend who helped create the technology that is allowing me to send you this letter
  3. Some notes on a very impactful book for 22 year old Jen
  4. A pondering on the importance of journaling
  5. A word that is typically frowned upon in society but is essential to learning
  6. A quote from a serial entrepreneur and venture capitalist on putting energy into things that pay off
  7. A question to get you thinking about your failure résumé
  8. A selfie with me, myself, and my favorite park in Chicago
  9. A shoutout to a couple of my favorite newsletter writers

Heads up this is a longer letter than usual. I had to get some things off my chest in my trimester review.

Now, let’s dive into letter 59 from a learn-it-all. Enjoy!

🤔 Reflecting

Over the weekend, I did a review of the past trimester to recognize patterns in the actions that you take. To follow the format of past reviews (including letters 54, 49, 45, 41, 37, 32, 28, 23, and 19). I compared it to my annual review and whether I met my goals. I have some recalibrating to do.

What I’ve loved

What I’ve lacked

There’s been a lot. To cut to the chase the biggest one making a pit in my stomach was that I barely wrote any content for my personal website. I’ve fallen off the wagon with my regular writing practice. I’ve felt in a funk and it feels good to get that off my chest. I’m going to change that and make some new goals. I plan to post at least two essays each month. Some ideas of what to expect these to be about:

What I will learn

Some personal projects I’m prioritizing in this next trimester:

Some professional projects I’m working on in the coming months:

🎬 Watching

In Steve Jobs' 2005 Stanford Commencement Address, he speaks to three specific stories about connecting dots, love and loss, and death. I highly recommend watching the full 15-minute clip. You won’t regret it.

My favorite part that give me hope about sour events is the public failure of when he got fired from Apple at age 30 after releasing the Macintosh.

What had been the focus of my entire adult life was gone, and it was devastating.
I really didn’t know what to do for a few months. I felt that I had let the previous generation of entrepreneurs down – that I had dropped the baton as it was being passed to me.

He was rejected big time. I cannot fathom the feeling of being  voted out of the company that I built especially alongside the people I was living day-in-and-out alongside through it all.

I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me.

The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.

During the next 5 years, I started a company named NeXT, another company named Pixar, and fell in love with an amazing woman who would become my wife.

Pixar went on to create the world’s first computer animated feature film, Toy Story, and is now the most successful animation studio in the world. In a remarkable turn of events, Apple bought NeXT, I returned to Apple, and the technology we developed at NeXT is at the heart of Apple’s current renaissance. And Laurene and I have a wonderful family together.

I’m pretty sure none of this would have happened if I hadn’t been fired from Apple. It was awful tasting medicine, but I guess the patient needed it.

He closes with saying: Stay Hungry. Stay Foolish. I agree.

📖 Reading

Tina Seelig, director of the Stanford Technology Ventures Program, put together a list of things she wish she knew when she was going to college for her son- who was going to college. She named this book What I Wish I Knew When I Was 20.

The book is a mix of practical advice on how to be more creative, how to create more 'luck', and some surprising life advice. I first read it in 2018 when I was 22 as I prepared to enter the "real world" as a post-graduate. It wasn't what I expected to read from a Stanford professor. She was (and probably still is) cool. Seelig remarks how the rules within the traditional education system are completely different than those from the outside world.

Some favorite quotes are:

On creating a failure résumé with you biggest screwups, an exercise I dusted mine off from 2018 that has a lot of updating:

This assignment has forced them to come to terms with their mistakes and to extract lessons from those experiences... It's a quick way to demonstrate  that failure is an important part of your learning process, especially  when you're stretching your abilities, doing things for the first time, or taking risks. People who have experience are hired to just because of their successes but also because of their failures.(69)

On how always trying to define ourselves in society puts limits on out potential and of what can be achieved:

We define ourself by our profession, our income, where we live, the car we drive, our education, and even our horoscope. Each definition locks us into specific assumptions about who we are and what we can do... We often make our own prisons, with rules we each create for ourselves, locking us into specific roles and out of an endless array of possibilities. (36)

On how life is the ultimate life open-book exam:

The typical classroom has a teacher who views his or her job as pouring information into the student's brains. The door to the room is closed, and the chairs are bolted to the floor, facing the teacher. Students take careful notes, knowing they will be tested on the material later. For homework, they are asked to read assigned material from a textbook and quietly absorb it on their own. This couldn't be any more different from life after college, where people are their own teacher, charged with figuring out what they need to know, where to find the information, and how to absorb it. In fact, life is the ultimate open-book exam. (11)

On why we should think like a scientist with all the data we collect from life experiences:

Yes, failure is hard. But it is a normal part of the learning process. Instead of looking at false starts and dead ends with regret, I suggest that you look at each one as a source of "data." Scientists do this all of the time. They know that each experience may lead to unexpected results. And the unexpected results are often a source of great inspiration. This is true in all parts of life. If you view each day as a series of experiments, you end up with lots of fascinating data that can be mined for valuable insights. (80)

💭 Pondering

Journaling is the ultimate way to see evolution of thoughts. I can think of no better pursuit that leads to self understanding than through the art of journaling.

🔎 Word to define

Failure: lack of success, an unsuccessful person, enterprise, or thing.

The omission of expected or required action; lack of compliance with the basic rules. A lack or deficiency of a desirable quality: a failure of imagination. The action or state of not functioning of a car engine or a heart; a sudden cessation of power; the collapse of a business.

Etymology: 1640s, failer meant "deficiency," and "act of failing," from Anglo-French failer, Old French falir "be lacking; not succeed". The verb in Anglo-French was used as a noun to mean "thing or person considered as a failure" in 1837.

Example: It is explicit on a report card or whether you pass a road test, but failure is also a feeling that mixes shame and sorrow together like a gross pickleback shot. It can happen in any pursuit of life where expectations are not met.

🌟 Quote to inspire

"If you throw gasoline on a log all you get is a wet log. But if you throw gasoline on a small flame, you get an inferno." -Gil Penchina

❓ Question to think about

What mistakes or failures are you glad happened because they helped you get to where you are today? Which screw ups are on your failure résumé?

📷 Photo of the Week

A shameless selfie in Lincoln Park processing my trimester reflection before my Reflection call with some Annual Review friends.

🙏 Shoutouts

I appreciate you reading this! If certain ideas resonated or you have feedback to improve my future newsletters, I’d love you to leave a comment, reply to this email, or send me a message on Twitter @JenVermet.

Never stop learning 😁

Until next week,


P.S. if you're interested in seeing the my half-baked failure résumé from 2018, look here.

If you’re reading this because someone shared this newsletter with you or you clicked a link somewhere, welcome! I’d love it if you subscribed below to receive future updates:


Subscribe to receive the latest posts in your inbox.