Nancy Collamer's Blog

As subscribers to my newsletter know, I’m a big believer in the power of questions. So I was delighted to recently find this article The Only List of Icebreaker Questions You’ll Ever Need on the the MuseumHack.com website. I combed through the list and pulled out ten questions that I think are particularly useful for readers thinking about their second acts.

After you’ve had a chance to think about these questions (and don’t forget to follow up each question, by asking “why?”) reflect on what your answers suggest about your second-act interests, values, motivators and sensibilities. And if you’re game, consider discussing your answers with friends or family members too. Their feedback might provide additional insights into your next steps.

Here are ten questions to consider:

What’s the best piece of advice you’ve ever been given?What would the title of your autobiography be?What fictional family would you be a member of?What was the worst job you ever had?If you could have someone follow you around all the time, like a personal assistant, what would you have them do?If you could eliminate one thing from your daily routine, what would it be and why?If you were famous, what would you be famous for?What’s one career you wish you could have?If you could choose any two famous people to have dinner with who would they be?If you had to teach a class on one thing, what would you teach?

Finally, if you enjoyed these questions, please sign-up for my free newsletter and get an instantly downloadable workbook of 25 Questions to Help YOU Identify Your Ideal Second Act.

If the economic downturn has you, or someone you love, starting a job search, it can be confusing to know where to turn for trusted advice. Below are sites I recommend for high-quality guidance, tools and resources:

LinkedIn.com has a collection of free videos for job seekers, “Finding a Job during Challenging Economic Times” featuring over eleven hours of training on topics like video interviewing, digital networking and writing a resume.Indeed.com recently launched a COVID19 Career Resource Center that includes job search webinars, links to state job resources, and a list of major national employers hiring right now.Job-Hunt.org has an excellent Guide to Successful Job Search for Job Seekers Over 50 that includes articles on LinkedIn Tips for Job Seekers Over 50, Remote Jobs in Retirement: What You Need to Know, and Beating the Too Old Bias, Learning New Skills, among others.Job search guru Hannah Morgan of CareerSherpa.net hosts a boatload of free resources for job seekers on her site, including checklists, a sample personal marketing plan, sample cover letters, conversation starters, assessments and more to help you navigate your job search.If you want or need to make a career pivot, these second-act podcasts will give you an endless supply of inspiration, encouragement and ideas for your next act: CareerPivot.comSecond-Act Stories.org Finally, for more free resources, please be sure to check out this post I wrote for NextAvenue.org 12 Free Resources to Find a Job, Start a Side Hustle or Change Careers .

In many ways, now seems like a crazy time to talk about your second act. The devastating impact of the coronavirus crisis on our economy, health and psyche has been staggering.

Simple tasks, like taking a shower or buying groceries from the supermarket are bigger challenges than normal. Tackling a plan for the future can feel overwhelming. 

Still, if you’ve read this far, my guess is that there’s at least a part of you that is looking for a way forward. Small, but impactful, steps that you take now to help you be in a better place once this crisis passes.

So I’d like to propose something for your consideration. Despite all the disruption to our lives, the one thing most of us have an abundance of right now is time. As Arthur Brooks notes in a brilliant column for The Atlantic, 

“We’re stuck at home; our lives on COVID time have slowed to a near halt. This creates all sorts of obvious inconveniences, of course. But in the involuntary quiet, many of us also sense an opportunity to think a little more deeply about life. In our go-go-go world, we rarely get the chance to stop and consider the big drivers of our happiness and our sense of purpose.”

I agree with Brooks. This time of “involuntary quiet” does provide us with the space to reflect on priorities, investigate second-act possibilities, connect with others and be of service to those in need.

Reflect. Investigate. Connect. Help.

Four foundational steps — creating the acronym R-I-C-H — that can enrich your life in pivotal ways, even during this uncertain time . Below you’ll find more about each of the four steps, along with resources to explore as you move forward:

1. Reflect. The first step in any transition is to reflect on where you’ve been, who you are and what you value. The good news is that as someone over age 50, you have a lot of life experience to reflect upon. As Steve Jobs noted in his iconic 2005 Stanford University commencement speech, ” You can’t connect the dots looking forward; you can only connect them looking backwards.”

To assist your self-reflection process, I’ve selected several posts that highlight books, exercises and questions that will help you connect the dots of your story. Admittedly, these readings and exercises take time to complete. But I promise that if you make the effort, it will be energy very well spent.

10 Questions to Help You Find Fulfilling Part-Time Retirement Work Options
Why Do You Want to Work in Retirement?
My Favorite Career Reinvention Books
The Secret to Finding Passion in Your Career
The Great Tool to Find a More Satisfying Career Path

2. Investigate. One of the biggest challenges people face when considering a second-act is to imagine options beyond what they did in the past. They grapple with questions like:

How do I repurpose my skills, interests and experiences in new ways?
Will my skills be welcome in new industries?
Are there courses, certifications or workshops that will enhance my marketability?
How can I take advantage of my skills as a gig worker or entrepreneur?

There are no easy or quick answers to these questions, especially right now. But there are a number of resources that can help expand your sense of what’s possible. Below you’ll find three posts that contain links to dozens of helpful classes, job boards, inspirational second-act stories and more.

100 Great Second-Act Career Sites
12 Free Resources to Find a Job, Start a Side Hustle or Change Careers
 3 Must-Know Resources to Help Launch and Grow a Semi-Retirement Biz

3. Connect. It’s impossible to know how the post-pandemic economy and job market will shake out. But one thing I can pretty much guarantee is that your next gig, volunteer opportunity or project will come about as a result of your professional or personal networks. Fortunately, with so many people working from home, now is the perfect time to reach out to contacts for good old-fashioned voice-to-voice conversations or video conversations.  It’s an ideal time to refresh dormant connections, check-in on people you care about and build richer relationships with people you’d like to know better.

Just remember that the purpose of these calls is not to ask for work, but to enjoy authentic, meaningful and mutually-beneficial conversations. If you feel uncertain about the best way to go about his, below are three posts that will help improve your networking chops:

5 Ways to Avoid Being a Networking Nitwit
How to Network with Younger People Effectively
Thinking of a Retirement Biz? Connect with your Industry Association 

4. Help. Finally, if you’re in a position to do so, I encourage you to find a way to be of service to others in this crisis. Helping others makes you feel valued and grounded, at a time when life seems to be spinning out of your control. And from a second-act career standpoint, volunteering or providing services pro-bono, can be a smart way to expand your networks, build skills and enhance your resume, while giving back.

Of course, most of you are already helping others. You’re checking-in on loved ones, volunteering with community organizations and donating to worthy causes. You’re organizing drives to collect protective gear for health workers and funds for people who are hospitalized with COVID19. Some of you are sharing your professional expertise through no-cost webinars, informational content, consulting and mentoring. Others are participating in artistic outlets, like the wonderful musical videos that have proliferated online in recent weeks.

But if you’re looking for ways to do more, or you simply want a better sense of what is out there, the posts below can help:

6 Great Sites if You Want to Volunteer in Retirement
Reinvention Resources: Nonprofit Careers
How to Do Work That Matters in Retirement

In closing, I’d like to share this quote from William Bridges book, Transitions: Making Sense of Life’s Changes. I hope you find comfort in his words that speak to our collective struggle and hope for a better tomorrow:

“You can’t follow the thread of your life very far before you find “the past” changing. Things that you haven’t remembered in years reappear, and things that you’ve always thought were so turn out to be not so at all. If the past isn’t the way you thought it was, then the present isn’t, either. Letting go of that present may make it easier to conceive of a new future.”

I often hear from clients that finding a satisfying volunteer role in retirement often proves more challenging than expected. It can take several attempts before you land the right role at the right organization. So before you begin to search for opportunities, spend some time thinking about what a good fit means to you. A few questions to consider:

What roles appeal to you? In other words, do you want to be involved with policy decisions, advocacy, program design, fund raising, etc. — or do you want to work directly with those in need?What roles do you want to avoid? Think about the jobs/roles you want to avoid (I don’t want to be involved with raising funds or I don’t want to get involved with anything that could be considered controversial).Which organizations or causes speak to you? The environment, social justice, the elderly, helping animals, immigrant’s rights, battling homelessness, etc.?How much time are you willing to devote to volunteering?

Once you’ve mulled over these questions, here are six sites to explore for ideas, advice and links to a great retirement volunteer gig:

Volunteermatch.org: VolunteerMatch is a portal that makes it easy to find volunteer opportunities that match your skills and interests.Catchafire.org: A service that matches professionals who want to donate their time and talent with nonprofits who need those skills. Projects range from one-hour virtual consults to multi-month commitments.Gen2Gen.org: If you’re excited by the idea of helping young people, be sure to check out Encore.org’s innovation hub for people 50+ who want to stand up for – and with – young people. There are many ways to get involved including listings of jobs, volunteer gigs, and much more. SCORE.org: As I wrote in this NextAvenue.org post, How to Become a SCORE Small Business Mentor, volunteering with SCORE can help you expand your professional network and pick up skills, while giving back to your community. SCORE needs working and retired professionals with a diversity of backgrounds and skills, but entrepreneurs who’ve had expertise running, growing and managing different types of small businesses are especially desired.Regional volunteer matching services: Many larger metropolitan areas have region-specific volunteer matching services. For example, I can search Volunteer Square for opportunities near my home. To find an encore career matchmaker in your area, ask friends for recommendations, check with your local library or do a Google search using “volunteer opportunities” and “name of your town or geographic region”National Park Service: Finally, a fun way to give back, travel and enjoy nature is to volunteer with the National Park Service. As I wrote in this post, Fun Freebies for Retirees these positions often come with attractive perks, including discounted meals and lodging.

As most of you know, I write a monthly column for NextAvenue.org, a PBS site where “grownups keep growing.” I took some time at year-end to read over my posts, and I enjoyed them so much, I decided to share them here as well! Here are my top five favorites:

Finding Passion and Purpose Through Work: You can’t find great part-time work without first understanding what “great” means to you. In this post, I explain how to reframe and broaden your definition of passion as an acronym — P.A.S.S.I.O.N — that highlights the different ingredients you want in a career you can be passionate about.

Second Acts to Profit From the Longevity Economy:  The longevity market — services and products targeting people over 50 — is enormous and growing. If you think you’d enjoy working around people in your age group (give or take a few years), this post shares four examples to inspire your next act. 

4 Ways to Start a Side-Hustle in Retirement: In this post I share what I learned from side-hustle guru Chris Guillebeau about starting, growing and enjoying a side-hustle.

The Secrest Sauce When Choosing a Second-Act Career:  People often ask me, “What is the most important ingredient when choosing a second-act career?” Experience, passion and profit-potential are all undeniably important. But as this post highlights, there is one critical factor that people tend to overlook when thinking about what’s next.

Fun Freebies for Retirees: A very fun read that highlights seasonal, volunteer and part-time gigs that come with cool perks and freebies, including deals on travel, dining out and theater tickets.

I hope you enjoy these. And please, feel free to reach out to me with any other story ideas you might like me to cover, either here or on the other sites I write for.

Whether you’re eager to start a new side-gig, find a part-time job or just want to get inspired about the possibilities for a fulfilling second act, these five books can help get you launched:

100 Side Hustles: Unexpected Ideas for Making Extra Money Without Quitting Your Day Job by Chris Guillebeau is a terrific read that tells the stories of “ordinary” people who’ve found clever ways to make money in the new economy. It will open you up to a multitude of ways you can generate income without working a full-time job.

Never Too Old to Get Rich: The Entrepreneurs Guide to Starting a Business Mid-Life by Kerry Hannon features interviews with 20 midlife entrepreneurs who share the challenges and lessons learned from their journeys. The book is filled with inspiring stories, practical tips, and solid advice.

Your Next Season: Advice for Executives on Transitioning from Intense Careers to Fulfilling Next Seasons by Dr. Leslie Wilk Braksick and Dr. William R. K. Innes addresses the unique challenges faced by high-powered executives transitioning into their “next season.” This highly relatable read is based on interviews with transitioning executives, as well as the author’s first-hand experiences coaching this demographic.

Retirement Reinvention: Make Your Next Act Your Best Act by Robin Ryan has plentiful advice on starting a flexible second-act career, including hobby-based businesses, temporary assignments and part-time professional gigs. There’s also an overview of volunteer and paid opportunities in the nonprofit sector.

Purpose and a Paycheck: Finding Meaning, Money and Happiness in the Second Half of Life  by Chris Farrell provides an uplifting look at what he calls the “second-life revolution.” This smart read weaves together research, insights from longevity experts and interviews with successful career changers.

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As frequent readers of this blog know, I am a big fan of Chris Guillebeau’s Side Hustle School podcast. Recently, Chris ran a story about two friends who have a side hustle selling cork sunglasses to wine aficionados. It’s an entertaining story that illustrates it really is possible to make money from your hobbies, if you’re willing to think outside the box.

In the podcast, Chris points out that there are 84 million regular wine drinkers in the US. That means there is a heck of a lot of money being spent within the wine industry.

But—and this is the important point—it also means that there is likely room for other types of services or products affiliated with that hobby. Often, people are more successful selling one of those affiliated services or products than trying to market the actual item or experience. 

In other words, instead of trying to compete with the big established businesses that control the market, look for an unmet niche within your hobby of choice.

For example, if you love wine, you can lead a wine-themed tour, or teach wine appreciation classes, or write a newsletter for wine lovers, or sell wine-related accessories (crystal decanters, customized wine charms, monogrammed wine openers, etc.) or, well, you get the idea.

Fortunately, there is no shortage of hobbies that boast large fan bases eager to spend their hard-earned cash (just think how much people shell out for tickets to the Super Bowl or for a special bottle of wine). Take a look at the newsstand in the airport and you’ll see entire magazines devoted to cats, crafting, chocolate, sports cars and fly fishing, just to name a few.

So what type of hobby-affiliated services or products could you provide in your next act? For inspiration, here are five fun examples I found on the Side Hustle School site:

A cat sitting service that pulls in between $1,500 and $2,000 a month by only seeing several clients a week.A baseball bat rental service, started by two former pro players.A self-proclaimed motorsports enthusiast starts an online auto racing parts and gear business.A former temp worker creates guided tours that allow tourists to eat their way through London’s chocolate shops.A marketing exec who starts a bike wine tour in an up-and-coming wine region of Canada.

Finally, if you’re motivated to explore ways to monetize your hobby, here are some other articles I’ve written on this topic:

How to Make Money From a Hobby in Retirement . How Your Hobbies Can Make You Money in Retirement . Want to Turn a Hobby into a Retirement Biz? 7 Questions to Consider

In today’s increasingly gig-centric economy, there are endless ways to repurpose your professional expertise into a more lifestyle-friendly career. For example, you could consult, freelance as an independent contractor, temp, or work as an adjunct professor, just to name a few.

It takes time to find just the right fit. But with drive and creative thinking, you’re sure to craft a satisfying solution. So, if you’re eager to expand your world of possibilities, here are 10 questions to ponder:

1. What services or products are being overlooked in your industry that you could fill? Within every industry, there are opportunities to create new and needed products and services. For example, you might sense a need for a new training program, a niche job board, or a specialized recruiting service, just to name a few.

2. What skills could you market on a freelance and flexible basis? Think in terms of your favorite and highest-value work related skills. What are you best known for? For example, perhaps you’ve been a star salesperson who could now coach entrepreneurs on ways to generate more sales. Or, you could leverage your bilingual skills to work as a translator for local law firms.

3. Do you have strong tech skills that you could offer on a freelance basis? Businesses and individual consumers hire freelancers to assist with a variety of tech-related tasks, including programming, web design, social media outreach and others.

4. What tools can you create to make it easier for people to do their jobs or enjoy their hobbies? Here again, take a look at what’s missing and figure out how you can plug the gaps. For instance, you might build a new tool, import a useful accessory or develop a mobile app.

5. How can you help mentor the next generation of talent? As the boomers move into retirement, more companies will look for help training the next generation of leaders. Perhaps you could offer individual coaching services or develop a mentoring program to assist their efforts.

6. Could you leverage your industry expertise as a consultant, board member or advisor? Companies pay well for counsel from seasoned industry leaders.

7. What services, events or initiatives can you create to make your industry more inclusive for all? More companies are focusing on diversity these days. Think about services or products — such as training sessions, conferences or guidebooks — that you could offer to promote diversity and inclusion in your professional world.

8. Is there a creative way to blend your professional expertise with your personal interests? There might be a novel way to use your professional skills in a totally different way. For example, I recently heard about a rabbi who now gets paid to lead tours to Israel for people of all faiths.

9. Have you developed a successful step-by-step business process that you could teach others? For example, if you created a successful executive on-boarding program at your old company, you might be able to turn that proprietary step-by-step approach into a book or online program.

10. What events or platforms can you create that will help connect your professional peers? People are always looking for ways to network with their industry peers. Perhaps you can create an association, conference, event or online platform to help connect them.

Remember, there is almost always some small piece of your professional background that can serve as the foundation of your next act. Happy brainstorming!

If you hope to work after retirement, you’ll want to be clear about your lifestyle priorities before moving forward. Here are five key questions to consider when planning your post-retirement work life:

1. How much money do you need to earn? If you need to earn a considerable amount of money to fund your retirement, that will drive your decision-making process. It might be easier to continue working in your current field, either as an employee or consultant, since that is how you’ll earn the most for your experience.

2. How much flexibility do you need? Workplace flexibility comes in many different forms, so it’s helpful to consider these issues:

Do you want to be location independent?  Perhaps you could find work that allows you to work from a sailboat. Or, maybe you’d prefer seasonal work that allows you to work in the National Parks during the summer and at a ski resort in the winter.
Do you want to work-from-home? You may want to focus on Internet-based opportunities, such as customer service, translation, writing or web design jobs.
Do you want part-time hours? If so, you might enjoy working for a local business or organization that typically hires part-time workers, such as a museum, library, sports arena, retail establishment or school.
Do you prefer project or gig work? Increasingly, retirees are embracing project, gig and temporary work as a way to work on a more flexible basis. For help with finding those opportunities, click here to access our list of 100+ Great Second-Act Career Resources.

3. How radical of a career change do you want to make? The reinvention stories about the accountant turned winemaker, or the policewoman turned personal chef are inspirational. But making a radical career change is rarely easy.. It takes time, training and a willingness to start over as a beginner. Sometimes a smaller shift – such as moving from a large corporate job to a nonprofit role or downshifting to part-time hours – can provide the boost you need.

4. What are your non-negotiables? Key to second-act satisfaction, is finding (or creating) work that aligns with your non-negotiables. Are you done with sales quotas? Only willing to travel 10% of the time? Do you need work that allows you to take summers off?  Before making a change, list out your non-negotiables so you’ll know a good fit when you find one.

5. What are the 3-5 most important reasons why you want to work after retirement? Finally, as I explain in this post Why Do You Want to Work After Retirement? there are multiple reasons why people choose to work past retirement. Identifying your top 3-5 motivators will help to guide and inform your second-act decision making process.

I was delighted to be a recent guest on the Small Business Spotlight on WCBS880. I hope you’ll watch my interview by clicking below, but I also want to encourage you to check out the other wonderful second act entrepreneurs featured on the site.

There are lots of fun ones to choose from, but two of my personal favorites are:

A former math professor who now hosts tours to places like Paris, Iceland and Peru as the Traveling Professor. It took him a while to figure out this business, but now many of his tours sell-out months ahead of time.
A man who combined his love of food, travel, and living a positive lifestyle with a knack for Instagram to become a social media influencer with a booming following.

Have a look and a listen. You’re sure to pick up some valuable tips and strategies that will help spark your next act.