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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