How did I end up here? How I changed careers, and you can too.

I’m Eddie Leonard (just in case you missed that from the site name) and I’m a Sr. Accessibility Technical Program Manager for Microsoft. Those who know me, know that I haven’t always been a PM. Before we dive into how I got here, let me give you a little background on my career.

Early on, when I was 22 years old, I joined the US Navy. Long story short, I was looking for a way to pay for college. When I joined, I had worked several jobs ranging from fast food to working in a movie theater, to forklift driver. Lots of different experiences, but none that was a career. I entered into the bootcamp as an E1 (bottom of the ranks) in the communications field. By communications, I mean actually patching in radio circuits for the operational folks to talk to other ships, aircraft, and send or receive messages. As technology was rapidly advancing, so was I. Within two years I had manage to rise to E5 and played a key role in piloting new communications technology, such as internet access at sea. Yes, I suppose you could say I was “insidering” before it was even a thing. My life as an IT Pro began here.

Skip ahead 5 years, I departed the Navy and landed a job working at a large financial institution as an IT Pro. Again, starting at the bottom of the ranks and worked my way up to consultant over about 18 years. I could write an entire book about a lot of my experiences here, and maybe I will someday. On second thought, it’s probably best I don’t.

After almost 20 years at the bank, I decided it was time for a change. An opportunity arose for me to take a vendor role as a program manager working on a couple of things in ideation that really aligned with my experience. I was at a point where I had to make a critical career shift decision. It was risky, moving from a long career as an IT Pro in a full-time position I was comfortable with, to a new direction where I did not have a ton of experience (or so I thought).

Do I roll the dice?

Let’s do it!

Now to the meat of why you are hopefully still reading this.

Making a career change is difficult, no matter where you are in your life’s journey. My goal is to share some of my experience and help you to be successful in your decision making about changing careers.

Step 1. Why do I want to make a career change?

This is very important to understand. Are you burnt out with the work you are doing? Are you looking for more money? Maybe you are looking for something that will allow you to spend more time with your family. It could be you are looking to make a bigger impact somewhere. Understanding your goal will help you both determine how much risk you are willing to take, as well as motivate you to do the work necessary. Yes, there is work to be done. For me, it was a combination of factors and not a single one that ultimately led to my decision.

Step 2. What do you want to do?

Ok, now you have the why, so it’s time to figure out what you want to do. Your why can impact your what so do not skip the first step. Part of my why was I was looking to make a bigger impact. I was fortunate to have an opportunity cross my plate that would allow me to do just that. The PM role at Microsoft presented to me was an opportunity to take my IT Pro skills and my experience as a veteran to help others learn new skills. Now that is impact! If you are not as fortunate to have something land in front of you, digging in and doing the work starts here. Think about things are you good at, or even just your life experiences. Try to line that up with a particular job. Try not to get caught up in imposter syndrome, or at what you CANNOT do and focus on what you CAN do. In my example, I was not a professional PM. This did not mean I could not PM, in fact as I looked at what I did in my role at the bank, a lot of that work was basically PM work. You have to remove the guardrails when looking at your next stop. Do not limit yourself to your previous job descriptions. That’s the whole point of changing careers. Look for jobs that fit your why, as well as something you feel you would enjoy doing. You may not be sure you will like it, but that’s ok. Be willing to give it a shot.

Step 3. Research and connect.

Next step is to research your new career choice. You are going to want to learn as much about what working in your new field choice is like. Talk to people you may know that are already working in the field. Ask them if they have any guidance for someone new coming into the field. Another thing is to take to social media (Twitter, LinkedIn, etc.) and follow well known people in the field. Connect with them if possible, and do not be afraid to ask questions!

Also look to see if your particular field choice has any “communities” you can join. Some examples are online forums, Facebook Groups, or even local in-person user groups or meet ups.

These new connections are invaluable not only for knowledge, but also for making other connections. Use these resources to get suggestions on what skills are critical to get you started. Ask your networks about the pros and cons of working in your new field. You want to make sure you have as much knowledge as possible to make sure you are comfortable saying you are ready to make the change.

Step 4. Become a sponge.

Why? Check. What? Check. Reseach? Done. Depending on what you have learned from step 3, you may need to do some upskilling. This could be learning about how to organize events, working with the Power Platform, or how to build the perfect flower arrangement. Whatever your new path is take some training, be it an online course or in person training. If you are transforming a hobby into a new career even better as you can skip right over this step.

Step 5. Update your resume (or CV).

Now you have the connections you need, and have learned some new skills, or improved on existing ones, it’s time to get that resume up to date. There are a million blogs, tools, and resources out there to help you, so I won’t go into the how to here. As Dona Sarkar would say, “Do the thing!”.

Step 6. Take the leap of faith.

Time to apply! Do not be afraid. It is scary stepping outside of your comfort zone, but after all, you’ve put in all the work needed, you now have some newly honed skills, and your resume is up to date. Apply for jobs you want, even if you believe you are not qualified. You may not land the first one but keep at it. Stay focused and stay positive. I know, it’s not easy but you can do it!

Now you have a framework to help get you determine if you are ready to make a career switch, and how to be successful should you choose to do so. Key takeaways are, do your research, make connections, put in the effort, and most importantly, do not be afraid to step out of your comfort zone.

So, how did that roll of the dice go for me? Pretty good, I’d say. I jumped in, took the opportunity, and did the work needed to get started in a new career. I quickly moved from the initial role I was brought into Microsoft for, to a new Community Manager role on the Windows Insider Engineering team, which eventually lead to my current role as a Sr. PM on Microsoft’s Accessibility Technical Team.

I’m not the only one who has done this. Many folks have, so you can too! If you are looking for additional resources on career switching or need a consultation for your resume, I strongly suggest you check out a colleague of mine, Ioana Tanase’s LinkedIn profile.

Hopefully you found this post interesting and helpful. Please feel free to leave comments and let me know if you have any additional tips, thoughts, or share your successful career switching story!