My name is Pam Lefkowitz and I’m a recovering IT Admin (here at JumpCloud they call it IT Columnist). I’m from the Chicago area and I’ve been doing IT for <mumblemumble> years. Some of you may know me on Slack or Twitter as @AlwaysDNS (if not, please follow – once in a while I say something fun). And when you come across the It’s Always DNS haiku, feel free to tag me. I’ve already seen it and always appreciate it. 

While my team and I are still fleshing out exactly what this column will be when it grows up, the basic premise is that you get to benefit from my years of being an IT Admin and running an ITaaS/IT consulting company. I was fortunate when I started Core, that I had a built-in client with a large tech company. Ah, those were the days…Apple clones were the name of the game and cell phones were clipped on our belts. Pretty on trend, eh? Building my company was relatively easy. There weren’t very many Apple consultants in Chicago at that time and it was easy to find me. Word of mouth worked well. 

A Woman in IT?!

For nearly all of my time in business I had a few things that set me apart from the others – I was the only female Apple consultant in the region, I was one of the first people in the country to hold Apple Server certifications, and when Apple moved to OS X (and created OS X Server) I became the one to go to about DNS. Life was good. I spoke up, I watched my speech patterns to make them more masculine. I gained clients across the country, I gained respect from my male counterparts (the gender makeup of the Apple Consultants Network was consistently about 10% female), and I finally got asked to present at conferences.

No sugarcoating, it was an uphill battle getting taken seriously as an IT professional. Women had to work 5 times as hard to get even a smidge of respect within the industry and from our male counterparts. And I worked hard. Super hard. I have been fortunate to mentor a number of women over the years and I hope that I helped ease the way for other Women in IT. 

I had many successes. I had my share of mistakes – but I recovered from them. And then about 5 years ago I made one bad business error and the walls came tumbling down. Suffice it to say, client lists should be treated like financial portfolios – diversification is key. I suspect that will be a topic for a future column. While lots of business mistakes are recoverable, not this time and the stress of trying to rebuild from the loss made working for myself not satisfying anymore. 


But, who was going to hire someone who had worked for themselves for 20+ years? And I had no resume. And I hadn’t interviewed in…ok, I won’t tell you how long ago my last interview was. I had experienced ageism and was even told by one recruiter that I should put on some makeup (I was already) and color my hair (I had no gray hair). I wondered if she said that to my younger or male counterparts. But I digress.

Fast forward 2 years to a sunny and warm Friday in June. I was away for a long weekend visiting family in Michigan, when I received a text from a friend/colleague asking if I was still interested in leaving IT Admin life. I said something like “Yes? Mayyyybeeee? Why? Huh?” There was a job that would be perfect for me and that I would be perfect for it. Eight interviews later (what a great idea) and, apparently, he nailed that prediction. 

Over the past month, I’ve spent my time closing up my business of 25 years and transferring my client IP to trusted colleagues in the area. I wanted each of my clients to be served by the local talent that suited them best. While my client list was not long, it was loyal. Finding the right consultant for each of my clients was the most important transition item on my list. My clients treated me like a business partner and many became good friends – it was critical that I fit them with the right person to take care of them. Saying goodbye was a crushing experience – for me and for my clients. 

New Day, New Opportunities

Now I’m here at JumpCloud as an IT Columnist and I couldn’t be more excited. I know it’s still the honeymoon phase, but I get to write to you folks regularly about Admin issues. I get to be creative. I get to work in tandem with folks who are masterful content producers, folks who do the IT hour, folks building our Admin community, and folks who care about growth. I know that when I get into a meeting there’s a better than 70/30 chance that I won’t hear anyone threaten to throw their tech out the window. 

Core was about 95% Apple-based. But IT Admin life is the same no matter the platform. Everybody knows us, they know our names, they know our numbers, they know where we sit – there is nowhere to hide. On any given day, we juggle way too many things, we are connected way too much, we set aside projects for emergencies, and we take on a LOT of stress. If you’ve done this for more than 10 years, you deserve a medal. It takes a special kind of person to be the glue, amirite? We have sharp wit and, sometimes, sharp tongues. We work hard, we play hard, and we are often misunderstood. 

This column will be a place to talk about issues germane to IT Admin life. We may talk about technology itself – it’s hard to avoid – but probably more about tech life. We’ll talk about business, relationships (betcha that raised your eyebrow, right?), customer service, security, reaching goals, movies, food, work-life balance, and more. I’m making lists to be sure. And we’ll carry these conversations into (or out of) our community boards, the JumpCloud Lounge, and the IT Hour. Got something on your mind and no one to talk with about it? Send it over…I can talk about anything (ask anyone on Slack) and I want to talk about the things that are relevant to you. You are not alone. I am about community building…a rising tide and all that. We can all do better.

So buckle up, we’re gonna have some fun here.

Published: 9/23/21 –

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