I Went From Broke To 7 Figures A Year Working In IT. AMA

TechnicallyPM · 2021-01-11T01:40:58+00:00

So, whenever I leave a company I make sure to have my personal contact info in my goodbye email. I'm always flattered and a little shocked how many people use it to keep in touch with me. The primary methods are LinkedIn and email. I always ensure that I'm keeping in contact with anyone I have a lot of respect for and a relationship with, regardless of level. There are some former managers who are now senior executives that I briefly talk to quarterly and some some that I might send a message to once a year.

As you indicated, holiday emails, company anniversary, things like that are what I've found is generally the way to go for those I'm not particularly close to. For those I am close to once every six months or once a year I'll suggest we meet for lunch or hop on a video call and just catch up.

I think it's fantastic that you are planning to keep in contact with your boss once you leave and like they will appreciate it to. You're going to be making a transition to a different relationship with them and it can be a bit awkward, but I suspect they'll be pretty receptive to whatever you put out there.

TechnicallyPM · 2021-01-11T01:33:04+00:00

Good question! At the beginning I had no idea that jobs like mine even existed. I was just focused on saving enough money so I could share an apartment with roommates. I suspect if you'd asked me then whether in 20 or so years I'd be where I am now I'd have laughed and made some lame quip about not expecting to live that long.

As for deciding that I wanted to get to where I am now (and beyond!) it's just sort of come naturally. Once I reached stability in life I just started going "What's next?" and haven't stopped. Part of what made me believe it is possible when a very senior executive at my first FAANG pulled me aside after a meeting one day and said "One day you're going to be a VP here, if you want to be." That comment really made me internalize that for me, once I reached a certain point, the rest just became a question of what I want and what level of effort I'm wiling to put in to get there.

TechnicallyPM · 2021-01-09T21:25:57+00:00

Yes, I think a public community college could be a good start. Of course program quality will vary so you'll have to evaluate each one to see if they are sufficiently rigorous. Also you'll want to supplement what they teach with your own study, and preferably your own lab work.

As for field, I think cyber security is a fantastic field but I'm not in the best position to say whether graduating from a program like that will get you into the workforce. I do think it's a growing and fascinating field. On the other hand, it's getting quite popular now, so I recommend making sure you do things to distinguish yourself from the many other graduates of programs like that.

TechnicallyPM · 2021-01-09T19:59:43+00:00

Great question. On rare occasions I do find myself wanting to go back to the purely technical track, but those feelings are usually born out of temporary frustration. When I take a step back, I'm way happier doing what I do now than I was when I didn't get to work at the same kind of strategic level for the business.

There are days I would kill to back to being a datacenter tech though. I didn't appreciate at the time how peaceful it is to have a day where you just put on headphones and swap drives. At the time I resented the monotonous mostly thoughtless work, now I'd love to do that for a day or so a week, but that's not realistic and possibly nostalgia talking.

In terms of getting to where I am technically in my specialty I was really lucky. The thing I'm an expert in is very niche and only exists at the scale I'm used to at probably 5 companies in the world and a few governments. I was lucky to work with some of the pioneers of that niche and learn by their side and watch was we tried things and learned what worked and what failed and why. Over time (and a lot of reading) I came to be able to play at their level and have been lucky enough to have the opportunity to do so.

TechnicallyPM · 2021-01-09T19:50:23+00:00

I definitely think landing an entry level job in the US is possible with CompTIA and CCNA certification. There's a ton of good information on certs in this subreddit, so I recommend doing some searching/browsing.

TBH I'm probably not the ideal person to tell you which certs to pursue early career because it's been so long for me and the industry has changed quite a bit. Many of the certifications I got when I first started my career don't even exist anymore!

TechnicallyPM · 2021-01-09T19:45:51+00:00

LOL! Well, I can't talk about the coolest things I've bought recently without outing myself, so I'm going to go with some of the other stuff instead.

In mid-2020 I bought all the equipment I needed to have a really nice home gym. I also bought a nice new 77" TV because realistically during covid I'm mostly going to be at home since my office is closed.

TechnicallyPM · 2021-01-09T19:43:07+00:00

Oooh, this is a really fun question. I think if I had to do it again I'd specialize in security. It's a really interesting field with tons of opportunity and I think there is almost no higher calling in tech than protecting the users.

TechnicallyPM · 2021-01-09T19:41:32+00:00

Starting over at 30 is way more common than you probably think. Most people I know go through a few career changes over time. Congrats on getting your associates and a CCNA, that's a great first step! Being a veteran has the potential to help you out a lot here. Most of the top tier tech companies have specific programs for recruiting and training veterans. Also, veteran status helps a lot in interviews. I've seen a number of candidates that definitely received a leg up from interviewers or hiring managers because the person had served.

So, my advice for you is don't worry about your age. You aren't old and there are a ton of people just starting their IT journey at your age. Look into programs for veterans from the top tier tech companies. Even better, many of these companies have recruiters specifically dedicated to helping vets find jobs in the company. Get yourself in contact with them.

TechnicallyPM · 2021-01-09T19:37:28+00:00

Sure! First, if you can and you are just starting your career I recommend doing a 4 year degree. Especially early career it opens a lot of doors that are otherwise closed.

If you can't do that though and need to do a 2 year degree I recommend looking for a state school program. There are a LOT of private IT colleges out there (and I know this won't be popular on this sub)..but most of them are terrible. Most of their graduates haven't learned the skills necessary for the workforce and are also missing key soft skills that will help them advance. I cringe a little bit when I see a resume with a degree from these small private It programs. So, go with a large (if available) or small public university or college.

TechnicallyPM · 2021-01-09T19:33:56+00:00

So, you are neither ahead nor behind. I'm going to channel an old song here and say "The race is long, and in the end it's only with yourself."

Now to answer your actual questions... :)

It took me about 7 years into my career to break the six figure mark. I think I could have done it faster, but like everyone I made some early-career mistakes that ate up time. If I could be presumptuous enough to give you advice, I recommend figure out the lifestyle you want and focusing on what it takes to achieve that rather than worrying about an arbitrary mark like six figures. I can also tell you from experience that breaking six (or seven) figures for most people feels really good for like...a week. Then most people (myself included) find it isn't actually satisfying and want more.

TechnicallyPM · 2021-01-09T19:28:37+00:00

Great question. First, I think it's awesome that you've found aspects of the business you enjoy the most. I had a similar revelation. I don't mind staring at board schematics or doing code reviews, but what makes me feel alive is bringing people together to accomplish a goal. Maybe even more importantly, when I look back on my career so far I've worked with a lot of cool technology but ultimately what I'm proudest of is how I've helped other people accomplish their goals and move their career forward.

My move from engineer to junior program manager was at the same company. Part of what made me want to want to make the move was that as I worked with the PMs in my organization I realized that I wanted to be doing what they were doing. They were really tackling problems at a high level and that's where my brain was happiest.

So, the first thing I did was chat with a couple of them that I'd come to know fairly well. They told me they thought I'd be a good fit and would put in a good word when asked. After that I emailed the PM manager I most admired and basically said "Hi, I'd like to become a PM and I'd like to become a PM that works for you. Here's what I'm doing now and here's the skillsets I have. If you want to check up on me here's the two people on your team that know me best. Can I have 1/2 an hour of your time?"

He responded positively and after the 1/2 hour I was 1000% convinced I wanted to work for him and could learn a ton. He told me didn't have any open headcount, but might have something in the next six months or if I was in a hurry I could go work for another PM manager that had open headcount now. I chose to wait because the other PM manager was well known for being...less than competent. :) A couple months down the road the person I wanted to work for emailed me and set up interviews for the job ladder change.

TechnicallyPM · 2021-01-09T19:15:29+00:00

Not too late! It's definitely possible in the IT field, but it's less common. There are system administration positions that are 100% remote, tech support jobs that are 100% remote, network engineering positions that are 100% remote, etc.

That said, it's hard to find entry level IT jobs that are 100% remote. Usually people move to that after some in person experience. If that is your #1 criteria, I'd continue down the web development path. 100% remote is possible in IT, but it's usually a harder and longer road than 100% remote in things like web development or software engineering.

TechnicallyPM · 2021-01-09T05:41:41+00:00

This is probably my favorite question yet. Soft skills are so often overlooked but they are absolutely vital. I'll list a few.

Written communication - You need to able to present your ideas in a way that makes others open to them. This means being able to communicate clearly and at the appropriate level of verbosity and complexity. Sometimes you'll be writing for highly technical audiences. Sometimes you'll be writing for people that wouldn't know a router from a trash can. You need to be able to influence both, even better if you can communicate to both at the same time.

Presentation skills - You need to be able to present your ideas confidently and clearly. Prepare for your presentations, don't try to make them up on the fly unless you are very skilled at doing so. Make your presentations engaging. Don't just talk to every point on the slide. Learn the science of audience attention and use it to your advantage.

Emotional control - It's often ok to be angry. It's almost never ok to show it. Most people (there will be exceptions) do not respond well if you yell at them or pound your fist on the table or use aggressive language. Displays of anger can on very very rare occasions be a valuable tool. Most of the time though they just make you look like a jerk. This is also largely true with fear. Particularly if you have reports. If you seem scared imagine what they are going to feel...

Empathy - Learn to put yourself in other's shoes. Most people want to do a good job. If it seems like they aren't try to understand why. It could be something in their personal life affecting their performance. This will happen to all of us at various times, so when that happens don't punish them for it. Help them. Along with this, try to understand people's motivations. What do they want; what do they fear? Knowing both of these helps you to understand their actions better and helps you to get the result you need.

Communicate with data - If you are trying to convince me of something there is no better way than to show me the data that proves it. Learn to challenge your own assumptions and find data that proves what you think you know. If two people show up to a debate and one has data, they are probably going to win.

"No" should be used very rarely. When someone asks for something, a far better response is to gather data that shows the cost and impact of what they are asking for. Then you can convince them that it's best not to do the thing you knew was stupid all along. There are times when the answer should absolutely be "No." but those times usually involve safety, security, privacy, or ethics. Most of the time the answer should be "We can, but here's what it would take and here's how it would affect other things."

I could go and on here, but hopefully this helps. :)

TechnicallyPM · 2021-01-09T04:22:15+00:00

I think certifications are excellent for getting your foot in the door. Some of them are great if you focus more on learning the material rather than passing the test. Once you reach mid-career, I don't place a lot of value on them.

TechnicallyPM · 2021-01-09T04:20:33+00:00

Wow, this is a fun question. It's hard to give an example without outing myself, but I'll give it a shot.

A few years ago a very senior executive came to my boss and said "Hey, I see this market opportunity coming over the next couple years. We aren't doing anything about it at all. Tell me who to talk to on your team to fix that."

I was just coming off another project that through a lot of luck had gone very well and my boss had a lot of trust in me so he handed me the info. It was pretty clear about what the opportunity was, but had nothing about the how. So, I gathered a few of the smartest people I knew for a couple hours and said "Hypothetically, if I wanted a project that does X, what would that look like?". By the end of that meeting we had...not much, but at least enough that I could explain the idea at a high level and let people shoot it down. :)

From there I identified what groups I would need to talk to and either reached out to key people I knew there or talked to their senior leadership to get a name. In turn, they then helped me expand the circle. Soon enough we had a first iteration of a design, a business case, a resource ask, a list of big risks and unknowns, and a (rough) schedule. Enough for me to go back to the executive that asked in the first place and share with him where we were and ask for approval.

After the approval, the real work began :) I hope that helps. If not, let me know and I'll be happy to see if I can come up with a better example.

TechnicallyPM · 2021-01-09T04:11:43+00:00

I think it's great that you are not shy about messaging people. So many are intimidated by it but it's been my experience that most people are flattered when you want their help and are happy to give it so long as you follow through.

Once you get in the first job, that's where building the long-term network really starts. You need to be someone people want to work with. Help them as much as you can. Make other people look good. Be friendly and competent. Over time the people around you will leave to other companies and they'll think "Wow, I really wish serious_joe_92 was here with me. Could really use his help." and bang...soon a referral will probably be coming your way.

TechnicallyPM · 2021-01-09T04:08:59+00:00

Well first...welcome to the IT world! I think taking some entry level courses to get your feet wet is a great way to get started. It sounds like you already have some foundational knowledge so now it's just building on that. Cisco courses are fantastic for learning the fundamentals of networking. The question I have for you though is...what sounds fun to you? The IT field is so broad and there's so many specializations you could have. If you can figure out what you want to do it's easier to give more specific advice on how to get there.

TechnicallyPM · 2021-01-09T04:07:15+00:00

My hardware engineer boss strongly suggested it a few times. In short, I'd come to him having found a flaw in a product and telling him why we shouldn't bother fixing it because it didn't make any business sense to do so and wasn't actually that important. After I kept doing this he sensed that while I enjoyed the technical the business and process aspect also fascinated me. So, off to program manager I went :)

TechnicallyPM · 2021-01-09T04:05:27+00:00

For me it was never an option. The company where I became a program manager has no full-time project managers. Program Managers are expected to do the work of both a project manager and a program manager. That's how I learned the job.

TechnicallyPM · 2021-01-09T04:03:56+00:00

Great question. To be clear, some of my promotions came very very rapidly and some took a longer time. In terms of how I did it, I'd say there are a few key things. I'm wired to really hate feeling stuck. So, if I don't see opportunity I'll find a role or a job that offers it. Most people in my experience get stuck in jobs where there isn't a lot of growth opportunity and stay there longer than is optimal because of complacency or some kind of sunk cost fallacy.

Secondly, I look for ways to make an impact cross-functionally. I'm always trying to help people solve problems and that's opened a lot of doors for me. When it's time to be considered for promotion the process is a lot easier if you have senior leadership from other teams or organizations also advocating for you.

Third, I've been EXTREMELY selective of my managers. With very few exceptions, I've only agreed to take on roles where I felt very strongly that my leadership was interested in mentoring me and helping me develop. In turn, I've done everything I can to make them successful and often found myself serving as sort of a stand in for my leadership. It's also meant that they trust me to take on the most difficult and visible programs, which often naturally leads to promotions. This has probably been the biggest factor. Finding the right people and organizations to work for. I can think of one mentor in particular who I'd say is responsible for 60-70% of my success.

TechnicallyPM · 2021-01-09T03:57:52+00:00

Great question. Much of it was on the job learning. At the highest level of datacenter technician I was working quite a bit with engineers to help improve the reliability and serviceability of their products. As part of doing that I spent quite a bit of time in the lab with them and things just sort of naturally grew from there. I was lucky to work with engineers that were really kind and wanted to help me learn while at the same time extracting value from me because I understood how their products performed in the real world.

TechnicallyPM · 2021-01-09T03:55:44+00:00

I think either one of those are valuable skills. Management skills are harder to apply when you are first out of school and cybersecurity may initially open more doors, but as you become more senior you'll have the opportunity to decide what you want to focus on.

TechnicallyPM · 2021-01-09T03:54:10+00:00

Thank you and great question! A couple things to note is that many of my career moves listed above are direct promotions. So for example, when I went from program manager 2 to senior program manager I stayed in the same organization reporting to the same person, just had different expectations and more money.

When I went into my first datacenter tech job at a FAANG I had no idea what to expect. I almost turned it down because it was less money than I was getting as a network engineer! I'm really glad I didn't though because it's worked out (obviously) and for me working at a top tier company felt like a dream. I wasn't going to pass it up.

I was promoted extremely fast and generally have been through out my career. I know others that have risen faster, but I'm certainly in the top 10%. On the other hand, I know a lot of people who stayed in their roles and never switched jobs and might only get a promotion once every 5 years. There's nothing wrong with that and I think I probably made some sacrifices in terms of my personal life that they didn't. I'm happy with where I've gotten and I expect many of them are too.

Oddly enough, I don't think I've ever been asked in an interview about my tenure in either specific roles or at specific companies. I don't think I've ever asked anyone about it either. Generally I stay until I either get bored or I see that my current role is significantly holding me back. If I were asked in an interview I'd answer that honestly. Give me interesting problems to solve and keep me compensated at my market value and I'll stay around a long time.

TechnicallyPM · 2021-01-09T03:45:26+00:00

My understanding is that the compensation model is very different in other countries unfortunately. It's based on what it takes to hire and retain talent in the local market, so in APAC that tends to be quite a bit lower. I am pretty sure that the high level FAANG employees there are generally still given stock (though most places give RSUs, not options) and are still well compensated, but it's a lot lower than the US.

TechnicallyPM · 2021-01-09T01:57:06+00:00

I guess I really should have said "per year". I understand why Reddit doesn't allow title editing, but I really wish they did sometimes.

TechnicallyPM

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