My first PowerShell Summit: Worth every penny

10 minute read

This year marks the 4th year that I intended to attend the PowerShell summit. I say ‘intended’ because last year the pandemic cancelled the summit, which made me quite sad because last year was the first year I submitted a proposal to speak that was accepted. That was a pretty cool feeling that was unfortunately shot down. But hey, 2021 is looking better as my same talk was accepted! So I hope you choose to catch my talk titled: ‘Practically Regexing: A demo of demos’.

My real intentions

However, my reason for taking the time to write this blog post is not only to encourage you to watch my session, it is mainly to encourage you to attend the PowerShell summit this year. And to do so, I have a good story for you. A story about someone that I know rather well. Myself. Specifically how I got myself to my first Summit, which was also my first professional conference ever.

A story about an IT guy

Once upon a time, in the same town that I’m typing this post, but a consulting stint, a couple contracts, and a job ago, I worked for a good company making decent wages and enjoyed a good work-life balance. My wife loved me, my baby daughter loved me, and life was quite good. Heck, I even thought I was pretty good at PowerShell back then. Little did I know that life was about to change.

I’d been at that job for around a year and decided that I’d put in to go to a conference, as that was one of the things that had been used to lure me in. They sent their employees to conferences and that was quite evident as I saw several of the other members of the Technology department do so. I did a bit of research and came up with the PowerShell conference. Unfortunately there was some budget issues and I didn’t receive approval until after ticket sales were closed. So I planned on attending the following year!

The following year came around, but this time my boss decided that I was good enough at PowerShell and should pursue a conference more relevant to a different product we used, but left the decision up to me. I found this to be a rather disappointing way to compliment someone’s skills and was quite bummed out about it.


It was almost too late when I realized that the ONLY person that takes my career seriously is me. My boss, while well intentioned, has the best outcome for his team and the department at heart. While that might be the best thing for the company, I am certainly my own person and have no vested interest in the company besides an at-will employment agreement. As my previous boss had told me, at the end of the day, I gotta look out for whats best for me and my family because there ain’t no one else that will.

With that in mind, I pulled up the PowerShell Summit registration page and was heartbroken to find that I had missed registration by literally a few hours. It wasn’t until later that evening that I put myself on the waiting list with nothing more than my hopeless optimism prodding me to do so.


One of my favorite parts of the PowerShell Summit is that it takes place within a reasonable driving distance of where I call home. And this characteristic was rather unique among all of the conferences I had looked at attending. With that vital bit of information, I reached out to the PowerShell Summit folks to just let them know that if they had any last minute cancellations that I would be able to take over without having to worry about flights or whatnot. Again, being an optimist at integral times, I put in for the PTO for the week of the PowerShell Summit, figuring that worst case I would have an entire week off to celebrate my birthday.

Surprisingly to me, With just under a month left I got a notice that there was a spot open and I had 24h to claim it. Just like every other cliche event in my life, I still very clearly remember receiving this email in the middle of the day on a Sunday while out running errands. I remember rushing home to claim the spot as fast as I could, even though the email clearly stated I had 24h. I’m laughing right now thinking about that! But I excitedly put down $1500 of my own money for the conference and another $500ish for the hotel (both a tax write off, by the way).

Worth it?

Its probably fairly obvious that I think that attending the PowerShell Summit was worth the money. But in contemplating its value, I had to consider all of the other things that I had spent money on to further my career:

  • I have a 2 year degree from a technical institute that, fortunately, didn’t cost me too much. Many years ago I would have considered that to be useful, but at this point it just checks that box for HR.
  • I have a few certifications that I’ve bought study material for and paid for some of the tests. At the time these were absolutely worth it. I can attribute a job to my first certification and pay increases to several of the other ones.

The one thing I’d never spent any money on was mingling with other IT professionals. At the time I got all of the ‘current’ information about my field from marketing newsletters and internet forum posts, neither of which are very reliable. That might work for an entry-level person with small aspirations, but that is certainly not my only ambition.


It was only the first day of the conference when I realized that it would absolutely be worth the $2k-ish that I had spent to get myself in that seat listening to Jeffrey Snover talk about Digital Transformation. Sure, listening to the Microsoft propaganda wasn’t my primary purpose for being there, but that kind of stuff was only the beginning.

I was in awe to see a talk on REST API PowerShell functions using classes, learning about PlatyPS, watching the inspiration for my upcoming talk: using regular expressions more regularly, getting introduced to PoshBot, and even a topic that I keep meaning to get more into, Pester. These were all talks that I sat in live, listening to someone who knew what they were talking about and was happy to answer questions about them! It was mind boggling how insanely cool of an experience that was for me because even though I felt like I was pretty good at PowerShell, I certainly hadn’t heard of the vast majority of the things I heard about in those sessions. I cannot stress how important it is for your career to see experts in your field talk to you about things that they find cool and important. If that happens, if that happens, I would recommand that you also find them cool and important.

Long term results

The last bit I’d like to leave with you is some real hard data. The week before my first PowerShell summit, I put in notice to quit my current. It felt both foolish and empowering, but after attending the summit and having my mind opened to the possibilities of what can be done with PowerShell, I would have put in my notice anyway. After the Summit I attempted to consult for a bit, then got into some contracting before landing a full time position at my current employer last year because of the pandemic’s impact on my business and contracting opportunities. That may not sound all that cool, but with the knowledge I gained by attending the summit, I’ve almost doubled my salary in 3 years. No joke. With the new view of PowerShell that I received by attending the Summit, I literally felt like Neo being pulled out of the Matrik for the first time. Thats how impactful it was for me and my career.


If PowerShell is a part of your primary skillset like it is for me, you should go to the PowerShell Summit this year, next year, and until PowerShell is no longer relevant to you. Which I hope is never because I love PowerShell. I love it so much that I get made fun of at work for it. People don’t ask me questions about how to do things unless they want a PowerShell answer because I don’t usually know how to update an Azure AD user’s group memberships or find the members of a Dynamic Distribution group or even run test REST calls without first launching PowerShell (and yes, PowerShell, not Windows PowerShell anymore). Its fun and I wouldn’t trade my career path for any other.

By now, if you have read this far, you should probably just buy a ticket. Here’s the link for 2021’s registration. See you there (virtually)!

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