[kelseyhightower]

Maybe I can help fill the gaps.

I ran my own computer store with a small IT consultancy attached to it for a few years. Then I chose to pivot and get a "real job". Things change once you're married with a child on the way.

Like many, I started out doing 3 months to perm contract jobs. The first contract was a Linux system administrator at Google in Atlanta automating the huge fleet of servers there. I learned enough shell scripting to be dangerous, but it was mostly racking and stacking servers, and provisioning top of rack switches -- hello minicom.

3 months later I was working in tech support, for more money, at a company called Vocalocity, who was early in the VoIP game. That's where I learned how to PXE boot and flash Cisco IP phones to work with our custom Asterisk based backends. I was there almost a year and then it was time to move on.

This would continue every three months or so. I held jobs at places like Cox Communications working in the NOC during the night shift so I could be home with my daughter. Three to six months later I quit.

I know what you're thinking, this guy jumped around a lot. I had to, money was tight, and it was the fastest way to get a raise, and it also accelerated my learning. Coming from being your own boss it's really hard to get excited about an entry level job and look forward to working your way up the corporate ladder.

My skills really leveled up when I landed a full time job at Peer 1 Web Hosting, where I started in Tech Support working tickets and taking calls helping people with Linux servers, Plesk, and MySQL. It's true, it's always a DNS problem.

Peer 1 is where I really learned how to write code, it started with bash, and eventually Python. I automated the SSL certificate provisioning system, and wrote some scripts that allowed me to close tickets faster than anyone else.

About 6 months later I was promoted to the engineering team and worked on our automated provisioning system for Server Beach, acquired from Rackspace, which was the part of Peer 1 that hosted YouTube before YouTube was bought by Google. Server Beach ran those "Latency Kills" ads to help sale dedicated gaming servers.

That provisioning system was responsible for allowing people to order a server back in the early 2000s from a web form and have it provisioned in less than an hour. We PXE booted servers, configured RAID controllers, and bootstrapped the OS, including Windows, and handed back an IP address and login creds to the larger system.

I was there for over a year before landing a job that would double my salary around 2008, 2009.

I joined the company mentioned in the article, TSYS, where I brought in a lot of automation, thanks Puppet, and learned enough Java to earn the respect of the broader organization and really help transform the place.

I was a Red Hat Certified Engineer (RHCE) from my days at Peer 1 and I leveraged that set of skills to package all the production applications into fat RPMs (Java, JBoss, and all the war files required to make it work) in the same way we use containers today. I also revamped the CI/CD system leveraging Bamboo with tight Jira integration. I also helped the company move on from CVS to SVN. Don't ask.

We had automated deployments and tight integration with our apps over the course of the 3 years I was leading the team. We automated everything from Oracle running on AIX, to provisioning SSH keys and access to production servers based on Jira tickets and Puppet.

On the software development side I learned enough COBOL to port some of our mainframe jobs to Python. I wrote packed-decimal libraries and EBCDIC encoders so we could use Python going forward to process batch jobs. A big deal in the payments industry.

During my time at TSYS I really got exposed to open source and made some major contributions to Puppet and Cobbler -- I added a feature to Cobbler that enabled us to configure servers while leveraging Cobbler metadata and tools like Puppet.

I also started contributing to distutils and pip back in the day. I did some of the work that made pip and virtulenv play nice together. I also started public speaking at local meetup, PyATL, in Atlanta, and found my voice in the Python community.

It's my PuppetConf 2012 talk that landed me a job at Puppet Labs, the rest is history.

[bradlys]

It's nice to see the resume listed out here. I did try to look you up on LinkedIn to maybe find out more (before writing my previous comment) - but found nothing.

For reference, I don't think you've jumped around a lot. I've had 5 different software engineering jobs in the 5 years I've been in the bay area. I moved to learn more, increase my pay, and hopefully find a rewarding environment. Still looking. Most everyone wants money, recognition, and control...

Do you think what the article wrote about is more important to your success (managing a standup act, mcdonalds, joining puppet) than the years that were not really mentioned? I wonder if maybe the person you were managed by, if the people who mentored you (if any), and what not were influential to your success and desire to push yourself out into conferences and making talks. I guess - I just wonder if your formative years of becoming a more senior software engineer meant nothing. Was it all just your own internal desires and no one would've influenced anything regardless and you were bound for whatever an L8 gets compensated?

[kelseyhightower]

I read it for the first time today like everyone else and love the way it turned out.

A lot of the technical stuff has been covered in other places. Tom pulled on a different thread, one that even taught me some things about myself. Tom did the homework, interviewed a lot of people, and presented the person behind the keyboard.

My current role does little to describe where I am today. The path for others will be different, and what I think is most important, beyond the technical achievements is the person I've become. The higher you go up in the engineering world the less you lean on the skills that got you there.

In my opinion the best engineer can change the world with zero lines of code.

[timeimp]

What an amazing "fill-in-the-gaps" comment!

I wonder, what was it like being the people who helped YouTube before they were a Google company? Did you ever interact with them on a day-to-day basis?

And with your payments stuff - how did those changes help the business you worked for? Faster batch reconciliation / processing or something else?

[jbarham]

> On the software development side I learned enough COBOL to port some of our mainframe jobs to Python. I wrote packed-decimal libraries and EBCDIC encoders so we could use Python going forward to process batch jobs. A big deal in the payments industry.

Great read, but as someone else who has worked on mainframes and in Python I found this especially impressive.

[ryukafalz]

> My skills really leveled up when I landed a full time job at Peer 1 Web Hosting, where I started in Tech Support working tickets and taking calls helping people with Linux servers, Plesk, and MySQL. It's true, it's always a DNS problem.

Tech support for a hosting company is a really sweet deal. It was my first real job in college (I’m aware of how incredibly lucky I was to have that opportunity) and you really do learn a lot in a short period of time.

[goku99]

Hey! Thanks a lot of sharing this. I find this a inspiring. You are the man who has worn every possible hat after all. All the best for your future.

- Random Internet Stranger.

[_cs2017_]

I was at your awesome talk at GopherCon some years ago, and it was one of the major reasons why I wanted to work at Google rather than FB or other companies. I kept telling all my friends to watch your recorded talks if they need inspiration :)

[Aeolun]

This post was easier to read than the article :)

[someday_somehow]

Thank you so much for posting this! I found many things in your story that are similar to my experience and it gives me hope.

I have a few questions I hope you don't mind answering as I'm trying to change careers to work full-time on public cloud for a technology driven company.

A little backstory (feel free to skip):

I began my career working in a company that did structured cabling, PBX systems and rack and stacking data centers. I was rapidly taking on more responsibilities and was managing a team of 40 people within 2 years.

Things were steady but I felt like I was missing out on all the incredible things that were happening in tech (I spend a lot of time on HN). After discovering AWS I was blown away by the possibilities and decided Linux and cloud were what I wanted to focus on as a professional.

I resigned to start my own consultancy and got the pro level AWS SA certification (with mostly self practice and no real-world production experience) and approached many businesses to sell services as an 'AWS certified' consultant. I got a few small wins but the sales cycle was longer than I expected and many potential clients would engage in long technical discussions but then cancel once they saw the TCO calculations.

The unstable cash-flow made things like paying rent on time very stressful so after two years I got a job at a small consultancy that provides mostly on-prem IT infrastructure services. I've learned quite a lot over the past two years and realized there were many holes in my knowledge. Yet, most of the clients' work was still on premise and now because of the pandemic many of them put their projects on hold or outright canceled them to cut costs. I've been furloughed without any income and right now I'm trying to survive by installing internet in homes and taking support calls while looking for a new job.

Many of the cloud related jobs - either solution architecture or Devops, require experience working in an agile software development environment, which is something I don't have and I have a major case of imposter syndrome because of this.

Now for the questions:

1) Is it possible to learn enough about agile practices and development to be productive without real-world production experience?

2) When you were looking for a 'real job' after running your own IT business, did you face any objections during the recruitment process on why you were looking for a job despite running your own business?

3) I was thinking of applying for 'cloud support engineer' type of roles because I really want to work in this field, but would that be a negative signal to recruiters because I'm an experienced (albeit in other areas) candidate?

After all these years I started to question if it was possible to go from rack and stacking to cloud but since you've explained it in such detail I see a path now. Thanks!

[kelseyhightower]

1) The answer to this lies in the question. Agile is a practice and it'll take some to get up to speed. One path I took was taking jobs in tech support, answering phones calls, and finding opportunities to engage with the product teams. You can start by giving feedback on the top issues you're seeing and breaking down ways the product can improve to reduce related support calls. And Boom, you are now apart of the Agile process, providing a feedback loop that helps development teams incrementally improve the product. You also help reduce support cost; don't worry, if you automate yourself out of a job, there will be a better one waiting for you.

That's how you open doors for yourself. Many great Q/A and operations engineers started in tech support where they honed their troubleshooting skills.

2) Yes, I use to get those questions. My answer was, "I'm starting a family, and I'm looking for something a bit more stable, and bigger challenges than the ones I was getting on my own".

It's all about being able to demonstrate your skills. Some times it's whiteboard coding exercises or logging into a live system and "making it work". My IT certifications helped me earlier in my career and now things like GitHub and blog posts are a great way to showcase your skills.

3) Remember, you can always tailor your resume for the job you want. If you want to avoid looking over qualified, then re-frame your experience to align with the job requirements. Instead of "I ran a business doing X,Y,Z", you can re-frame it, "As a _ I did X,Y,Z".

During the interview you can show off your full skill set by giving deep answers demonstrating your understanding of the big picture and how to make a business impact.

If you ever want to discus this stuff further, shoot me a DM on Twitter, I've been where you are, and I know what's possible.