Hindsight, as the saying goes, is 20-20. Most of us would redo, or undo, at least one decision, likely more, that we’ve made while trekking down our career paths. From the TechRepublic member feedback I’ve gotten on this issue, the litany of regrets clearly isn’t limited to job roles and working in IT.

While some members cited making the ”wrong” job role choice, many others spoke to very personal choices and actions that ultimately impacted their workdays, personal lives, and career experiences.

In the spirit of learning from others’ mistakes (which is obviously less painful than learning from one’s own), I wanted to share just a few of the dozens of regrets that members sent over when asked to contribute feedback on the topic.

How being loyal can be a career killer
Mal Grieve was a server operations manager within a financial services company when she faced a political and personal action dilemma. Her boss was not viewed highly by others within the business unit, and that issue soon became hers as she had to choose a side—his or the opposition’s.

She chose to remain loyal to her boss, and the decision ultimately hurt her advancement opportunities.

“I expect to receive as I give, and so as long as someone is my boss I will give him or her unfaltering loyalty, as I expected from my team,” she said. As a result, she lost her managerial status in the reshuffle that followed her boss’s swift departure. Her only career advancement option left was to move on to another company, she explained.

“I frequently ask myself how I could have played it differently and always come up with same answer: I couldn’t. In the harsh world of office politics, you can only play properly if you have no self respect or conscience, both of which I’d like to think I have in abundance,” said Grieve, who is a now a project analyst specializing in configuring new systems on NT platforms.

And while she may regret it, she wouldn’t have played it any differently except for one aspect: “I’d enlighten my boss as to the general perception others had of him, which would undoubtedly have been painful to hear,” she said.

What can happen when you don’t do job due diligence
When one IT professional applied for the MIS role at a nonprofit social services agency (where he had previously worked 12 years ago), he thought he asked all the right questions about the job expectations, as the resulting list was pretty intense: develop MIS strategy, manage desktop/end-user support, develop budget, stabilize network infrastructure, maintain servers, and implement new systems as the need arose.

It turns out that the issues he didn’t think to ask about—the training budget, IT respect level, user education—would ultimately make the tech leadership role a huge, stressful headache.

Yet it wouldn’t be fair to blame the outcome on the MIS manager, as he believed he had a good sense of how the agency operated since he had worked there at one point. But, as he unfortunately discovered, a lot can change in 12 years.

Now in his third year in the job, he regrets not doing more investigating before accepting the role.

“Management has repeatedly proven that it has no realistic concept of how MIS works,” he said. “There is no understanding of how MIS should be aligned to support the agency goals and objects,” added the MIS manager, who requested anonymity.

The lack of IT knowledge and appreciation has thwarted not only IT projects and efforts but the leader’s own career goals, networking opportunities, and job requirement needs.

“As MIS manager, only the absolute minimum training is provided, and it is nowhere near enough. Although I have worked with all Microsoft operations systems, I do not have nearly enough levels of experience with server-based applications, yet I am expected to manage those systems to perfection. There used to exist a MIS committee consisting basically of other managers and supervisors. One day, out of the blue, our CEO decided to sit in on one of our meetings. At the end of the meeting, he dictated that there would be no more MIS meetings.”

Not taking a chance and relocating
While Tim Poole is content and has enjoyed his long career at HP, the senior consultant has often wondered how his career, and his life, would have turned out if he had made different decisions at the start of his IT tenure.

Two times, in his early career, he turned down jobs that would have required moving to different locations.

“One job would have put me in London, a city I’ve always loved, but my ex-wife didn’t want to live that far away from her mother. The other job was in Hawaii but the pay scale was lower than I was willing to accept,” he explained. Each time he’s visited Hawaii, he’s wondered how it would have been to live there, as he misses it when he’s back home.

“I’m enjoying my current job and career, but I’ve always wondered where I would be today if I had made either of those ‘other’ choices.”

Chaos is sometimes good
About six years ago, “John M.” (an IS manager who requested anonymity) had a chance to be in charge of IT operations for a small north Georgia university.

He didn’t take the role for several reasons.

“The infrastructure (not to mention the entire faculty) was chaotic, lacking in any sort of standardization of equipment,” he recalled.

In fact, the whole interview process was so chaotic and negative that he couldn’t wait for the interview to end. When it finally did, six hours later, he declined the job offer that came his way.

“However, what I thought was horrible probably would have been a gigantic opportunity to grow in terms of skills and management ability,” he said in retrospect. In taking the safe route, at a small nonprofit agency, his skills have become outdated and stagnant.

“Sometimes, a seemingly ugly situation can present beautiful opportunities,” noted the tech leader.

Trust your first instincts
For one TechRepublic member, the big regret was not sticking to his first instincts during a reorg situation.

The member had served 15 years as the IT manager for a subsidiary of a large banking institute (with almost 20 years service in total), when the executive level decided to centralize the IT functions for all the subsidiaries.

“Although I was initially opposed to the centralization, I eventually embraced the idea, and turned down an offer from the CEO to remain with the subsidiary,” recalled the IT leader.

That decision was made three years ago, but the career impact is still lingering.

“It took me more than two years to find my feet in the organization again, including going through another round of restructuring,” he explained. Today he is managing a small but key technical team but “has lost a great deal of ground in terms of influence, benefits, and so on.”

Sometimes, he noted, there’s a lot of truth in the old cliché, better the devil you know than the one you don’t, said the South African-based professional.

Staying too long
While there are not nearly enough opportunities that provide life-long careers these days, one TechRepublic member’s tale illustrates the negatives of longevity with a sole employer.

“I regret having stayed with one company for 30 years. While there have been some rewards, the pigeon holing that has occurred has stymied my ability to grow technically within the company.

“In years past, I have been able to grow technically and to accept many interesting and challenging projects both here and abroad. However, time and age have crept up on me and, according to my HR department, I am ‘no longer technically advanceable.’ Great euphemism for being too old for new tricks,” said the tech professional.

To compensate for the now-defunct challenges and opportunities, the TR member has spurred his own skills development path, learning C++, ASP, Java, and XML as well as keeping up to date with Visual Basic and Visual Fox Pro. He’s now learning to use .NET.

“At home, I design and develop Web pages and Web applications part-time for a consulting company. The extra income is nice, but the satisfaction I derive from being able to produce up-to-date applications is better,” he said.

His employer, he noted, is familiar with his abilities but believes that only those who have graduated from college in the last five years have the requisite talent to do new technology work.

“I think they are being a bit shortsighted. Sometimes the gray hairs help provide a certain ‘maturity’ when estimating the resources development will take. Even if you take a gamble and lose, you will have grown in your ability to handle adversity and maybe, just maybe, win greatly because you dared greatly.”

And yet, leaving too soon can be a mistake
Richard Byrd related that his worst career decision was to retire early—at age 56—to set out on the project management consultant career path a few years ago.

With his certificate of training in project management from Colorado Technical University in hand, he then watched the economy throttle potential contract positions he had been eyeing.

The opportunities, he said, “went spiraling into the toilet, along with my plans.”

Now, after two years of odd jobs and countless applications, he works as a volunteer with the IT Samaritans.

“We are a group of out-of-work IT professionals who do volunteer IT projects for nonprofit organizations in Colorado. Although I miss being gainfully employed, the satisfaction I get from staying active doing what I like while doing good things for my community keeps my self-esteem intact,” said Byrd.