mr. r. s. braythwayt,

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What I've Learned From Failure
What I've Learned From Failure

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A Humblebraggadocious Letter

PagerDuty People

Dear N—:

Thank you for reaching out to see how my career is going, and to open the door for investigating opportunities with G—. I am pleased to hear that I have come to your attention.

Once upon a time, G was much smaller than it is today. Its place in the technology firmament was not secure. Its people and investors were making risky bets on the future of the industry, and there was a sense of adventure, of making the future rather than preparing for it.

I am in a very fortunate place right now. I work with PagerDuty, a company that–while insanely modest by G’s standards–is also trying its hardest to invent the future.

Everyone (and alas, every-thing) is connected to IT operations. Keeping those operations running smoothly is the key to keeping just about every business running, whether it is an old-line company running its internal systems, or a feisty innovator attempting to disrupt an old-line industry.

And that makes PagerDuty such an exciting product, and such an exciting company.

It is deeply satisfying to work at the nexus of lean product development and engineering for high availability at scale. I work with a great team, in a wonderful culture, and it is also deeply satisfying to be a part (no matter how modest) of growing our team and culture so that we continue to be a great place to work in the future.

I know that opportunities with G are prized. There is the chance to work with outstanding people on mind-bogglingly hard problems. And rumor has it that my pay would at least double were things to work out. That matters, I have children, and while money is just a number, financial security for them is no trifling consideration.

But in the end, I am aboard a small, fast ship sailing into adventure. No matter how tempting, I will not leap into the sea and swim towards G’s sleek, modern, and leviathan-like aircraft carrier.

I am fortunate enough to be doing exactly what I’ve always wanted to do with my career, and in closing, I will say that I hope you are too, and wish you the best of luck finding good people for whom working at G would be doing exactly what they always wanted to do with their careers.

Warm personal regards,


Reginald Braithwaite


For much of my life, I could not honestly write a letter like this. For most of my life, I have been interested in self-fulfillment the way people watch TED talks: For the vicarious thrill of engaging with climbing Maslow’s Hierarchy of Needs, but without the plan, intent, or means to work my way up from shelter and safety.

This is not a bad thing in and of itself. It would be an act of gross arrogance to believe that there is nothing more important than working on interesting problems with people you like.

But if you should look at your life one day and realize you have a chance to work your way towards being able to write a letter like this, why not do so? You needn’t have the crashingly poor taste to humblebrag about it, you can just do it for its own reward.

I’ll close with the celebrated words of Richard Hamming:


Also, in case it isn’t a well-known fact, being cold-contacted by a recruiter from a large company does not actually mean that you are considered a prized prospect for employment. It just means that your name and email address has been hoovered up by a giant, automated recruiting machine.