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I am 59 and have worked as an IT contractor for over 20 years. Recently, my contract ended, and I’m transitioning away from my primary career. While I’m financially able to retire, I’m open to taking on less demanding paid work if the right opportunity comes along.
For those who retired from your primary career but later did other paid work, how did that happen? Did you plan it, or did the opportunity find you? Was it through networking, volunteering, former colleagues, or something else?
After years in the workforce, I came home to raise our twins and eventually homeschooled them through middle school. During that time, I worked part-time for a nonprofit for nine years before “retiring” to help care for my mother in her mid-90s. Along the way, I managed several family estates, including a complex probate estate, as well as my mother-in-law’s and my mother’s affairs.
After my mother’s death, my sister, an RN, and I were asked to help an older woman in our hometown navigate aging-related challenges. We helped her remain safely in her home for several years and later assisted with her transition to skilled care after a serious fall. Through those experiences, I gained firsthand insight into the gaps in support available to older adults and their families.
Around the same time, I managed the estate of my best friend after she died of cancer during COVID, deepening my exposure to end-of-life planning and estate administration.
I thought I was retired. My husband and I traveled, and while we were financially comfortable, I wasn’t planning to draw Social Security until age 70. Then a financial planner friend asked if I could help some of her older clients. The idea intrigued me. With a CPA, MBA, and a career that included commercial real estate, construction management, relocation, and a wide range of financial responsibilities, I realized I had skills that could make a meaningful difference.
What began as a part-time venture became a growing Daily Money Management practice. Today, three of us help clients manage their day-to-day finances and navigate life’s transitions. The work is challenging and rewarding, and it gives me the flexibility to enjoy regular travel and time with family. Best of all, it has allowed us to preserve our retirement savings while continuing to do work that genuinely improves people’s lives.
There’s nothing wrong with knitting or other retirement hobbies (I tried knitting and was terrible at it), but I find deep satisfaction in helping clients solve problems, maintain independence, and face life’s challenges with greater confidence.
I was in IT, network security, then cybersecurity in the five prior years before retiring at age 63 (2013). I had not planned on working after retiring. During my retirement dinner, the previously retired CEO of the company attended the dinner and asked me if I would meet with someone the following week. He was a bit secretive and did not want to discuss the details at that time. Since this retired CEO was also the person that hired me 31 years ago, I agreed without hesitation. It turns out that he was on the Board of Directors for another company (non-competing) and felt that my experience would benefit this company. They were interested in transitioning part of the company to cybersecurity. At the meeting (with the CEO of this new company), I was offered a six-month task to help them evaluate some options on how to proceed. The level of effort was one day per week (on average) and the output would be a two-page monthly status report with an oral presentation on my conclusions presented to the board. Most of the six months activities were visiting potential companies for acquisition. Rather than worry about billable hours, they offered me a very generous retainer for being available up to 40 hours per month. If I needed to spend more time, a formula for extra time spent was incorporated. Working one day per week from home netted me over 60% of my previous full-time job! If I had known such an opportunity was available, I would have “retired” sooner.
I completed the task as requested and was offered an amendment, extending the work agreement for another six months. As the company transitioned to this new role, my job was to advise the CEO, CTO, and CISO directly (as an alternate advisor) following the acquisition. This continued for three years, at which point, I wanted to end the agreement. They came back and offered a one-day-per-month agreement, in that they still wanted some “independent” advisor (not influenced by corporate “politics”). I agreed for two more years, at which point, I felt my value was not worth what they were paying me. Additionally, I really wanted to get rolling on our Roth conversion plan, especially since the TCJA was going into effect in 2018. I had laid out a six-year plan to convert 40% of our portfolio to Roth. However, working part-time would impact the amount of annual conversions we could do (while staying within our tax limits).
Both true for me. My strict requirement was PT jobs where I could make my own schedule. I did consulting, executive search, and preventative maintenance on kiosks. Strongly encourage as a defense against the risk of a stock market swoon at the early years of retirement (sequence of return risk)
I retired from a megacorp just before I turned 62, took a great, planned vacation with my wife, got home and realized I wanted to keep working a bit. I just hung a shingle on LinkedIn for doing similar work I did in my career and ended up doing part-time consulting for 8 years. I started out working with ex-colleagues at firms who brought me in and then got some referrals. I just finished working before my 70th birthday in June.
Good for you.
Good question. I truly believe everyone and there journeys are different.
After 33 years of commission route sales and the hectic pace and hours that went along with it I knew I didn’t want to sit around or start a similar rat race in retirement.
Living in a smaller town it’s all about connections, everybody knows someone so it’s fairly easy to find a job. A lot of it is not what you know but who you know.
I retired for three days 😂 before starting to work at our Middle School as a teachers aide. After almost fifteen years of that I retired again. I have now worked seasonally for the last eight years in our city’s Parks department, enjoying the outdoors at a much slower pace along with no pressure of any kind
Thank you for the very timely article and helpful responses. Per my “Fear of the unknown” post a few weeks ago, I find myself in the exact situation as Jeffrey. Over the past several weeks I have been exploring various lower paying, but potentially rewarding roles to pursue once my severance runs out. This includes visiting local places like the bank, library, supermarket, hardware store, Town Hall, etc. and observing the people at work. How old are they? Do they look happy? Could I see myself doing this? I have also been asking if there are any licenses or specific qualifications required so that I can pursue them while still receiving severance. This research has given me purpose and revealed some interesting results. At 59, I do not think that I am ready to veer too far away from the finance/investment field that I spent my career in, at least not yet. But there are plenty of ways to leverage my experience and help people, provided I get properly licensed. Yesterday I picked up Securities Industry Essentials (SIE) for Dummies at the library and based on my initial review of sample questions, I have my work cut out for me!
Thank you all for sharing your experiences and advice. I really appreciate the time you took to respond. One theme that stood out to me was how many opportunities came through relationships and simply staying engaged with the community, rather than through a traditional job search. That’s given me a different perspective on what my next chapter might look like. I wish everyone continued health and happiness in retirement.
I’ve done a lot of jobs since my official “retirement “ 15 years ago at age 57 due to a layoff. Fortunately I was fully vested in my union pension. Moved from California to Colorado, got my CDL and drove a gas truck for 6 years. Did a lot of very scenic (and sometimes scary) mountain driving. My wife tired of the cold winters, so we reretired, sold the house, bought a motorhome and started traveling. Found a company that paid us to travel doing gas line surveying across country. Did that for about 4 years and settled down near my oldest son to be near grandkids. To keep from being bored, I drove a school bus for 2 years. Now I only drive for overnight and longer field trips because they pay me for every hour I’m away from home. So it’s been a very gradual transition to fully retired.
I work part-time preparing lab materials at a local college. I love my little job — a half-day or so each week, for two semesters a year, mostly on my own schedule. The work is intellectually interesting and provides for socialization and interaction with students. I also enjoy the feeling of responsibility the work provides.
The position materialized soon after I retired, when a former colleague and friend related how he was doing lab prep as part of his teaching but was clearly overworked. I volunteered to help, provided the college would cover me legally. They did; I worked as a volunteer through that first semester and continued on in a paid position thereafter.
After 42 years in the TV news business, I retired two days shy of my 63rd birthday. I never intended to retire that early, but I’d reached my personal expiration date for the demands of that industry. I still wanted to work in some capacity, and the thought of working for my parish library system appealed to me.
Just a few days after I retired, I saw an opening for a Library Associate position. I applied, and after a hiring process that took several months, I was fortunate to get the job.
It’s full-time with benefits, but far less demanding than my previous career. (Of course, it pays less, too, but that’s fine at this stage of my life.) I feel lucky and blessed, and I can see myself doing this for many more years.
Excellent question. I was downsized at age 48. A friend ask me to join his company which competed with my previous employer, the catch no salary, only commission. Decided to take the opportunity, and it worked out great. So went from 50 hours a week, to 30 hours, then at 65 more like 20, and then down to 5 hours a week. As you can see I really liked what I was doing selling inkjet ink and parts, and finally at 78 decided to fully retire. The nice part about it all, is I worked from home since 1994 and because of the internet could work from cruise ships or anywhere in the world. It was the best downsizing ever.
I worked as a software engineer. When the Megacorp told me my pension wouldn’t increase after I reached 30 years service, but I could start drawing it then, I decided to take early retirement and get in some travel. Thinking I might need to supplement the pension, and ready to make a change, I planned to reinvent myself as a tech writer. I did my old job as a part-time contractor for nearly a year while I took writing classes at a local university (they turned out to be more useful for a future journalist, but I enjoyed them). When I got back from my first long trip I got a part-time job as a tech writer at a local start up run by former colleagues. I fully retired a few years later.
So, a combination of planning and networking, I suppose.
Jeffrey, while I think that it’s generally better to have a workable plan, sometimes things happen by accident.
When I left my job selling and delivering beer, my plan was to have a new career in financial services. If that didn’t work out, my fallback plan was to climb back into a truck.
I fell flat on my face in financial services, but the job presented me with the opportunity to establish my income tax practice. That certainly wasn’t part of the plan, still, things worked out very well.
Best of luck
I retired as pastor of my church at age 71. Years earlier I had been trained to do transitional interim ministry and because of the need of a nearby church, I was able to do interim ministry part-time, beginning the month after retirement. The point is that if skills are transferrable, it can lead to rewarding part-time work.
For me it was quite easy, I could be viewed as having a few retirements. For my first I was a government employee with an early retirement expectation based on age and years of service. When I reached the minimum requirement at age 51, I left after finding a new job through a former colleague and began collecting my pension as I matched my salary in the new job. The key to the transition was letting people know that I was available otherwise they think you are content in your government job.
Later, that employer merged with another company providing the opportunity to leave with a separation package. That’s when I determined to go out on my own and consult using the various contacts I had in government and through the recent employer. It worked out magnificently as I formed an LLC and began making maximum contributions to an SEP IRA thus reducing my income while saving for the final retirement which I now enjoy through all the components created by the various jobs.
I retired early from a technical job with a long commute , and have been fully retired since. I think if you are just out and about in the community , opportunities will quickly find you. As only one example , I went to the bank one day , and when I mentioned I had retired , they said hey why don”t you come work here? My local YMCA usually has shifts for the front desk and you will meet many people that way – that will almost certainly lead to interesting opportunities. Or just going to the Y you meet other members. Going to the doctor or dentist can also lead to some work when you tell them you are retired. They still ask me once in a while .
I retired from MegaCorp April 2018. Admittedly, I took a “We (my wife and I) will figure it out” approach to retirement we only had a rough plan to increase travel and a specific long-term plan to visit all the National Parks and spend more time with distant family. We took a trip to a National Park (Yellowstone BTW) in May 2018. It was great. But by July I realized I wasnt quite ready to hang up my cleats. So I hung a shingle on LinkedIn to do some consulting which I did for the last 8 years part time. For the most part its been great, allowing us to travel to some great places after and between work trips, see family and afford a few splurges. I say “for the most part” because there were a few times when it got busier than I wanted to be. As far as specifically how it happened, when I hung the shingle on LinkedIn, I got contacted by a former colleague for some work and that work led to another big project with another firm. I did get most of my work from former colleagues and referrals. The work has been mostly the type of work I enjoyed when I was employed and not the type of work I didnt enjoy. I turned down quite a bit of work and was fairly selective about it as I was in a position where I did not necessarily financially “need” the work. I just turned 70 in June and this year I have only done one small piece of remote work and I am ready now to full retire. Overall, a great experience.
The day after I retired, my neighbor, who owns a funeral home, asked me what I was going to do with all my time. I told him a few things I planned to do and he asked me to consider doing part-time work for the funeral home. So, I now work visitations and funerals, drive the hearse, and other odd jobs for the funeral home. My last school administration position was as director of finance and human resources. I tell people now that I am still in human resources, just a different type…
I’m from Chicago.
It was the traditional “one of my siblings knew SOMEBODY who worked at a not-for-profit which needed my skillset”.
The pay was much less. So was the stress level.
When I set my LinkedIn profile to ‘Open to Work’, opportunities started finding me. I also had some options arise from my company network. Ended up working part time for a little under three years, averaging about 15 hours a week. It was a great transition for me. Still turning away unsolicited opportunities. I was fortunate that my particular set of skills and experience happens to be in high demand and low supply these days. Never experienced age discrimination at any time in my 40+ year career.
Ken – glad to see you’re still on here.