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This article was written by Office Apps and Services MVP Mark Rackley as part of the Humans of IT Guest Bloggers series. He shares about some of the lessons he learned along the way that will hopefully help YOU take your career to the next level.


13 years ago I started on a journey that would forever change my life and my career in ways I would have never imagined. I went from working a simple 9-to-5 job while living 2 miles down a dirt road in rural Arkansas to owning a business, traveling the world, and becoming internationally recognized for my expertise… while still living 2 miles down a dirt road in rural Arkansas. What’s really amazing is that the opportunities afforded to me by jumping in and embracing the amazing Humans of IT are truly open to everyone! Sometimes you just need to know what’s out there and how to get started. Allow me to briefly tell you about myself and some of the lessons I’ve learned along the way that will hopefully help you take your career to the next level.

My Story

I’m a developer by trade. I’ve always been able to figure stuff out on my own, pretty decent jack-of-all-trades for most of my career. I never needed much help. Then came SharePoint. I’m sure many of you have similar stories. It was 2007, I was sitting in my office minding my own business, just doing my job and my boss walks in and says:

“You need to do SharePoint”

I’m like… SharePoint? What the heck is SharePoint?! So, I searched online and still had no clue what SharePoint was. For the next year of my life SharePoint was a four letter word. I couldn’t figure out how to make the most simple things work well. There wasn’t a lot of related content available online at that point and my frustration grew daily. For the first time in my life I realized I that maybe I couldn’t do this on my own, and needed help.

I went to my boss and humbly said, “We need training”. To her credit, she heard me, paid a lot of money to bring in a trainer… and you know what? That trainer didn’t know anything about SharePoint either! He couldn’t answer any question that wasn’t the most simple out-of-the-box answer. We ended up getting a refund on the training. My frustration only grew further…

One day, while searching for help online I ran across a conference in Tulsa, Oklahoma, about a 3 ½ hour drive away. It was a free event, AND they had a SharePoint track. Could this be it? Could this be my chance to get some answers? I made the journey with a couple of coworkers and it was here that my life changed. I met a few people that are still active in the SharePoint community today. Among those were Eric Shupps, Becky Isserman, and Cory Roth… and these people actually KNEW something! What’s more, they were more than happy to share their knowledge and experiences.

Eric encouraged me to start blogging and to stay in touch (so, really all of this is his fault).  
I dove right in. Started blogging immediately and building relationships in the community. I was attending more events. Within 6 months I was speaking at regional events and attended my first Microsoft event (SharePoint Conference 2009). I even organized my first SharePoint Saturday! Looking back on my blog post about 2009 (ah, the memories!), I really dove in headfirst.


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Within 2 years I was speaking at Microsoft events, at one point had the number 2 SharePoint blog in the world. 2012 was another big year; I had the overall number 1 session at the Microsoft SharePoint Conference and was soon speaking at conferences all over the country. In addition, while speaking at a conference in San Francisco I met my future business partner and fellow MVP/RD Stephanie Donahue. Fast forward to 2015; I join PAIT Group as a partner and received the esteemed MVP award. It’s hard to believe that my very first trip to the Microsoft campus in Redmond was my first MVP Summit.

These days, I continue to speak every opportunity I get, and I’ve helped grow PAIT Group into a thriving business. I currently organize one of the largest community events in the US: The North American Collaboration Summit in Branson, MO that brings in speakers from all over the world. I’m also part of the Techsplaining Podcast with three other awesome MVPs: Stephanie Donahue, Rob Foster, and Brett Lonsdale. 

Because of these crazy Humans of IT, I have a career I love, friends literally all over the world, and have been on some amazing adventures including a 3 day road trip through Bosnia and floating on innertubes in New Zealand through caves while looking up at glow worms… ALL while still living 2 miles down a dirt road in rural Arkansas. Nothing has changed, except that I’ve greatly expanded my horizons and world view thanks to the power of community!




I’m now at a point in my career where I feel I can better mentor those coming after me and try to do what I can to make their journey as fulfilling and enjoyable as mine as been. These opportunities afforded to me really are available to everyone – you just need to know where to find them.

For the remainder of this already long blog post, let me see if I can pull some kernels of wisdom from my experiences to hopefully help you along in your journey.

How to Get Started
Sometimes the hardest thing to do is to just get started. Maybe you feel like you aren’t quite adequate? Maybe you are wondering why people should listen to you? One thing I’ve learned over the years is that you can learn something from EVERYONE. Don’t discount your knowledge and experiences. 

Just get started
Yes, there are people out there that know more than you. Yes, you might make a mistake, and yes, unfortunately there are people out there who like to point out mistakes. Here’s the thing you need to understand. No one else has your voice, your experiences, and your perspectives. You are uniquely YOU. To this day, the easiest and most valuable way to get started is to blog. Blog about what you know. Blog about your frustrations. Blog about that thing you figured out so that you can remember how to do it again, and teach others how to do it too. 

My son is interning for us this summer and I’ve started encouraging him to blog whenever he figures something out. He has trouble understanding why he should blog when he figures something out. “It’s so simple though, and isn’t the documentation already out there?” I have to explain to him that the “documentation” doesn’t always makes sense to a lot of people or they fail to understand the WHY’s of something. Often explaining “why” is more important than “how”. If you can save one person hours of searching online because you blogged about it, they will remember. Also, when you forget how you did it last time, you’ll have it nicely documented. It’s a win-win!

As Vesa always says, Sharing is Caring.

Take a risk and be okay with failure
Here’s the thing, before 2008 I had NEVER spoken in public before. In fact, the first time I ever spoke at a conference I finished in 30 minutes… and it was a 60-minute session! I still remember just standing there thinking, “Well… crap!” and I distinctly remember the guy at the front of the room saying “Well, I can see you are passionate about it”.


I could have decided to be embarrassed, go to my corner, and never speak again… but I didn’t. And you know what? I’ve discovered I really love speaking. Everything about it. I love the travel, meeting people, sharing my knowledge, making friends… just all of it, and I never knew this about myself! If I had not taken a chance and pushed through the failure I would NOT be where I’m at today.




Find your people
And here’s another thing. When you fail (and you will fail at some point – everyone does!) there are going to be people out there to lift you up. I really have made some of the best friends of my life because of this community of folks. It’s an amazing feeling to be able to have dinner with a friend in basically any city or country I’d care to go to. Not only are they amazing people, but they make me better at my job. I explain to people all the time that I’m not an expert in everything, but there’s a 99% chance I know someone who IS the expert of any particular topic and we are good enough friends that I probably have their number and can ask them. Here are just a few of the people who’ve made this experience worth it. 




At this point, I feel like your crazy uncle who can’t stop talking, but I’m reminded of another story. Several years ago I was sitting at home and my phone starts ringing. It was fellow MVP Fabian Williams. Fabian asked: “Where’s your wife?”. I thought this was an odd question, and I explained she was sitting right next to me. He then proceeds to tell me that he’s at a SharePoint event in Philadelphia and this woman walked up and said she was my wife. He puts her on the phone and it was actually my cousin playing a prank… I know what you are thinking… I’m from Arkansas, so my cousin could be my wife… but that’s not the case here!


What had happened is my cousin was out at the same location as a SharePoint Saturday Happy Hour. She had heard the word “SharePoint” and knew I did SharePoint. So, she goes over to the group and starts eating their food. When she was questioned, she said “it’s okay, I’m Mark Rackley’s wife” and Fabian was like “Oh really, let’s see…” and he gives me a call… 

Where was I going with this? Oh yeah… find your community. These people are awesome. They are the friends you will cherish for life no matter where you are in the world, and I’m thankful for them every day.

Find your Blue Ocean
Are you struggling to get involved in the community? Can you not seem to get traction? Having problems getting selected to speak? There’s a great business book called “Blue Ocean Strategy” and I think it can help in multiple facets of your life. Basically, there’s a red ocean and a blue ocean. The red ocean is where all the sharks are and the water is just bloody with them fighting it out to be the big fish, while the blue ocean is where no one is at. It’s not crowded. In fact, it’s totally empty and full of space to grow. When you are looking to add value and create content, are you creating content in the red ocean? Where everyone else is fighting to be seen? If you are one voice out of thousands it is often difficult for you to be heard. Find out what you can do that not everyone else is already doing. How can you personalize it and add your spin to it? As a conference organizer, I can tell you it’s really hard to pick sessions when there are DOZENS of Microsoft Teams governance sessions being submitted, yet I have a hard time filling a Power BI track. If you are having problems standing out, then maybe you need to be standing somewhere else? Find the place where YOU can shine. 

Love what you do
Going back to my first failure where someone said, “Well, I can see you are passionate”… Whatever you do, find something you are passionate about. That passion comes through, draws people in, and ensures that it’s not a burden on you to do. There’s a LOT of ways to give back, including blogs, speaking, organizing, podcasts, answering support questions, mentoring, or simply sharing what you’ve found useful. The point is, no matter what you do, find something you love to do.



Lessons Learned
I wish I could say that in my 13 years of doing this I never made a mistake, that it was always rainbows and unicorns, and that I never stuck my foot in my mouth. Your journey will likely be layered with failures, embarrassment, and lessons learned the hard way. It happens to everyone – just make sure you learn from your experiences.

I hate being rejected. It stings, every time. Even now, when I submit sessions for a conference I get rejected, quite often. What really hurts is I love to speak and I KNOW I’m a decent speaker, but I still get rejected. So, what do I do? I try again… and again… and again…

If it’s important to you, don’t give up. Keep trying.

I was first nominated for MVP in 2010. I was rejected every year after that until 2015. Rejection sucks. Don’t give up. Continue doing what you love, build relationships, and do your best to enjoy the journey. After all, the journey’s all part of the fun!

Be Kind, Be Humble
I wish I could say I was always kind and humble. I wish I could say I never got an attitude. I wish I could say I never scoffed at what someone else was doing. I wish I could say I was a better person, but I’m human. If I could go back in time this might be the best advice I could give myself: be kind, be humble. Keep in mind, you were a newbie once too. That thing that is so simple for you now, is a struggle for others. People are going to make mistakes and say things wrong. People are going to give wrong advice. How do you want people to treat you if you make a mistake? Do you want them to pounce on you? Tell you that you don’t know what you are talking about in the most public forum possible? Would you like to be ridiculed and turned into a meme simply because you didn’t know any better and were trying to help? Before being too harsh with anyone, take it as an opportunity to be kind. Pull them aside and correct them, offer guidance. About half the time they’ll get defensive and lash out, but the other half will be extremely grateful and they’ll remember that moment and you created another valuable relationship.

On the flip side, remember we are all humans. We all have bad days and tough times. We lash out because of something else going on in our lives and we don’t always handle stress well. Learn to have some grace with your fellow Humans of IT and let us make mistakes from time to time. We can all still learn from our mistakes.

What’s next?
So, what’s next for me? I honestly don’t know. Now that I’m a business owner and manage a team of people I have less and less time to play with the technology as much as I like which has impacted my blogging. I don’t get to speak at quite as many events as I used to. Does that mean I’ll be less involved with other Humans of IT like you? I sure hope not! I think it certainly changes my perspectives. Now instead of technical blogs, I’ll blog more about business impact. Instead of speaking as much, I hope to mentor others to get where they want to go. In fact, if you are interested in being a mentor and/or mentee, download the free Humans of IT Community Mentors app and join other global Humans of IT looking for mentors/mentees on there. Feel free to reach out to me on there as well – I’m always available to help mentor where I can! 


Now, don’t get me wrong I will still speak as much as people will let me and my hope is to just enjoy this ride for as long as it lasts. I’m thankful for every day of it and thankful you made it all the way through my ramblings. Maybe you gained some insights into who I am as a Human of IT, maybe you gleaned some wisdom. Regardless, thank you for all YOU do to make the community a better place. I know you will make a difference in the lives of others in tech. 






Brought to you by Dr. Ware, Microsoft Office 365 Silver Partner, Charleston SC.