6 Takeaways from a Rather Unremarkable IT Career

I recently left my 20-year information technology (IT) career to be a full-time blogger

Most of my career involved partnering with a large government customer to modernize its massively-complex and outdated IT systems.

My teammates trusted me. Managers gave me challenging assignments, and I exceeded expectations. 

The client was always happy with my work.

But I didn’t climb the corporate ladder or invent cool products or processes. I didn’t oversee large teams or manage millions of dollars. 

My contributions had minimal impact on the big mission — the projects I supported represented tiny fractions of multi-billion dollar budgets.

Despite 20 years of experience and deep domain knowledge, my work rarely moved any needles — which may have been a symptom of career dissatisfaction.

Much of my work helped to avert potential problems instead of moving the organization forward. 

In large IT projects, individuals can only contribute so much. Visible success takes hundreds of contributors and three to five years.

Yet one mistake will land the organization on the cover of the Washington Post.

Now I am starting a new solo “career” that’s more aligned with my interests and the lifestyle I want to live.

I move the needle every day.

If I were 23 again, I wouldn’t just follow the money. I’d look for opportunities where my skills could impact a mission I care about.

Here are six takeaways from my 20-year IT career that I think apply to many professions and my work today.

1. If you reach the point when you don’t like your job, you’ve waited too long. 

I spent fourteen years with a mediocre employer. 

The owner found ways to incentivize me to stay whenever I was itching to leave. 

It was a scrappy company.

I knew it wasn’t the right employer for me during most of my time there. 

But I stayed. 

Good project teams outweighed employer mediocrity.

I compartmentalized the two, mostly enjoying day-to-day work but cringing at any headquarters interaction. 

In part, frustration due to employer discontent led to starting this blog and doing it anonymously.

Moreover, limited job satisfaction motivated me to save and invest my way out of an unfulfilling career. 

I finally left that employer and joined a much better one for the last five years of my IT career. 

In hindsight: 

  • I should have been more willing to take career risks (especially before kids)
  • I should have explored other career paths during the earliest signs of discontent
  • I’m grateful that I started blogging about money

Instead of waiting until you’re unhappy to find a new job, change jobs more frequently (internally or externally) to challenge yourself before getting complacent.

Explore more opportunities to find better roles for your skills and avoid becoming content with something you don’t enjoy.

Create unconventional opportunities for yourself. 

2. Brevity is essential in modern communication

I wrote several executive presentations at the tail end of my IT career. 

Each PowerPoint slide can hold a lot of information using a 12-point font. 

But executives don’t want a lot of information. They want the key points, briefly — pretty pictures on one page, if possible. 

Executive presentations need to tell a story, which better be clear on page one or two. 

But simultaneously, executives don’t want to read anything. 

In the post-COVID-19 corporate world, brevity is more important than ever.

Meetings pollute executives’ days.

When meetings are remote, most everyone on that call is eager to hang up, pee, and get another coffee before the next call.

I started approaching executive communication as if I were presenting to a child.

Simple diagrams and tables. Few words and big fonts. Ten seconds to make a point. 

Online content is similar. 

Bloggers use catchy headlines to grab attention, short sentences, basic charts, and simplified diagrams when possible. 

TikTok videos are 60 seconds. Tweets are only 240 characters. 

This section is already too long. 

3. Meetings are crushing the workforce

Before remote work became more prevalent, in-office meetings were shorter and more effective. 

Most office workers enjoy personal interactions but also like the privacy of their personal workspace to focus on tasks. 

When you’re working from home, meetings feel constricting in the place where you should be most comfortable. 

Before and after COVID-19, I often found myself in two-hour online meetings with more than 100 people.

Maybe six of those people actually spoke. 

Those kinds of meetings might be unique to large government IT projects.

Everyone on those calls knew they were ineffective and a waste of time. But the invite lists grew. 

There were young, smart people on those calls, and I’m sure the meetings were as soul-crushing to them as they were to me.

Meetings are too frequent, too long, and lack productive outcomes. 

Status meetings should only be 15 minutes.

Weekly team meetings need a tight agenda, and attendees should come prepared (instead of late and out of breath from the last meeting).

Most meetings should be no longer than 30 minutes, with no more than 5-6 people.  

Anything longer is a working session. Anything bigger is an all-hands.

Follow these guidelines to improve your meetings*:

  • Fewer meetings
  • In-person when possible
  • Action item ownership
  • Shorter meetings
  • Clear meeting agendas and intended outcomes
  • Only essential attendees

Despite most people agreeing that meetings were a time-consuming problem, there was limited effort to reduce them during my tenure.

The most effective solution for meeting fatigue is the decline button.

* Full disclosure: The author did not follow these guidelines in his previous career. 

4. Too many planners and compliance people and not enough coders

I supported enormous IT projects with hundreds of contributors.

But on the largest projects, I never met a coder. 

The teams I interacted with wrote ubiquitous strategy documents, designed fancy project roadmaps, and maintained a trail of supporting compliance artifacts.

Coders were out there somewhere, but I never interacted with them. 

The government is required to maintain documentation to comply with laws and oversight. If I were in the private sector, maybe my observations would be different. 

But from my experience in IT, there are too many managers, non-technical contributors, and compliance folks and not enough engineers and “needle movers”.

I suspect corporate office workers of the largest Fortune 500 companies experience a similar dynamic.

Big tech sees it too. Here’s what Elon Musk said about his first days at Twitter:

The organizations I worked with understood this was a problem, but struggled to fix it.

Good engineers are in high demand and expensive to hire. Excessive compliance documentation was required for audits and CYA.

The solution to this problem is bold leadership, though probably not as extreme as the new Twitter owner.

Effective leaders must eliminate non-essential tasks, address dead weight, and find efficiencies without alienating the workforce.

But it’s hard, and most leaders are apprehensive about stirring the status quo for fear of backlash. 

5. The loudest people make most of the decisions

Voice volume and confidence carry weight in professional organizations. 

More weight, at times, than the ability to make strategic decisions.

The loudest voices are often the worst listeners too.

In my field, risk-taking was mostly discouraged. Few wanted to ruffle feathers, speak out of line, or challenge authority. 

The primary incentive was to avoid making mistakes. 

So if a loud voice was willing to stick its neck out and make a decision, most stakeholders wouldn’t question it, right or wrong. 

Verbal confrontations in the office cause stress and ruminations that can follow you home. 

This dynamic cultivated gossip and Monday morning quarterbacking.

So most people just keep their mouths shut, even if they have good ideas. 

The best managers and decision makers listen well, harvesting ideas from all voices, soft and abrasive, and use what they learn to make the best call possible. 

The worst dictate the path forward and avoid blame when a decision goes sour.

There were a few times I had to make a critical final decision and relied on the most experienced teammates for input. 

Other times, I was vocal, only to be ignored because the client or senior leaders determined the problem to be unfixable.

But most of the time, I chose the more silent route to avoid confrontations and ruminations.

I wasn’t passionate or stubborn enough to push as hard as was needed. 

6. In-person is better 

Remote teams became a thing long before COVID-19.

I’m old enough to remember when desktop computers and clunky monitors were the norm and teams couldn’t work remotely.

I started seeing signs of team performance atrophy precisely when laptops and connectivity enabled a more scattered workforce. 

Teams work much better when they are co-located most days of the week.

But remote workers still prefer remote at the detriment of the organization. 

I preferred being a remote worker — and it probably made me worse at my job.

Not bad, but worse. 

Commuting sucks, but it separates the day between work and home life.

Our brains need that separation.

At home, I am more distractible.

The office provided a better space to focus on tasks, plan, develop new ideas, and collaborate with colleagues.

In-person conversations are more productive and meaningful than Microsoft Teams small talk.

Face time with the “higher-ups” is crucial if you’re aiming to reach the next level.

Elevator conversations were my least favorite part of corporate life, but better than no conversations. 

Though I felt more disengaged from my job during 2020-2022, while most coworkers were remote, I still liked it better.

Getting the kids to school was easier. There was less rush.

After-work activities started earlier — I’d be at the pool with my kids at 4:15 pm every day instead of stuck in traffic. 

Household chores became a welcome distraction from endless meetings. 

I could sleep more without waking up early to shower and dress for work.

Nearly everything about my work-life balance was better as a remote worker.

In-person collaboration suffered, and I was OK with that. 

When my teams started meeting in person again, gatherings were more productive, morale increased, and more work got done.

But one day a week was plenty.

Startups and small businesses have moved to remote-first, and big corporations have accepted hybrid work models going forward. 

There’s no turning back after COVID-19.

But companies enforce in-person requirements at their peril.

Yeah, some people like going into the office. Especially the people who live nearby.

But workers want more career flexibility, not less. In a tight job market, strict policies that limit flexibility will inhibit retention and recruiting. 

Companies with a strict in-person policy will need to entice workers with higher pay and more meaningful missions and global impact.

Those that succeed will thrive. 

The rest will chug along.


I left my career less than two months ago.

As I settle into self-employment and the months pass, I’ll surely revisit this post to see how my attitude changes. It’s easy to remember the negatives.

But I already miss parts of my last job:

  • The people
  • The benefits
  • The nice office buildings
  • The feeling of belonging to something bigger
  • The support my employer provided my family and me

I can always return to consulting and have those things again. Or find another employment opportunity that gets me excited to wake up every day. 

Blogging does that now, so I’m grateful. 

Featured photo via DepositPhotos used under license.

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  1. Very much agree that consulting is an option to get back most of the things you miss about work while still avoiding most of the things you didn’t like, if you can control the hours you spend. At least it was that way for me the first five years of retirement when I was consulting enough to make a meaningful amount of income. Now I turn down just about all of the potential consulting gigs I am contacted about because I get enough satisfaction from the fairly intense volunteer work I am doing. It will be interesting to continue to follow your journey.

    1. If I go back to consulting, it will be a very careful reentry. A lot of what I learned over the past 20 years will be applicable to the next 10-20 years. So the option is there, but the temptation is not at the moment. Thanks for sharing your take, Steveark.

  2. Craig – glad to hear you made the leap. Be curious to read something on how you fill your day and a little more on planning your financials. Owning my time is the ultimate goal now. Thanks for a great blog and advice on building streams. -Dan

    1. Thanks for chiming in and for the suggestion. I’m still sorting out how I approach my days. They sort of feel like they haven’t changed that much, except I have way more free time now. I really need to be efficient because the days fly by quickly while the kids are in school. Next week, I’m thinking about a post about how I’m using our investment income to fund a part of our lifestyle now. Assuming I stick with that topic, let me know what you think next week.

  3. Raj Aggarwal says:

    When I was reading your blog, I had a wide smile as I could relate to many points in this article. It is very nicely articulated by you. I am looking forward to reading your financial blogs and how you plan your financials. This is something I think about and maybe one day…

  4. I spent over 4 decades in “a Rather Unremarkable IT Career” before I completely retired back in the 2010’s.

    Your 6 takeaways are 100% accurate.

    The reason I retired, though, is not because I didn’t like my job.

    It was because I didn’t feel that I was able to contribute more than 110% of my pay (salary and benefits) to the organization. I felt as though I was no longer able to be a net positive.

    I do hope all my children will be able to retire at a younger age than I was.

    Very interesting blog.

  5. Great post Craig, I work for a private company in the Healthcare Field and i’m here to tell you everyone I work with on the Hospital side, is inundated with meetings, chats, emails, spreadsheets, yada yada, but little actually gets done. It’s scary the amount of bureaucracy that is crept into healthcare, and I think the delivery of healthcare is being compromised because of it.

    1. That is scary to hear from the inside. It’s obvious how screwed up it is on the outside.