Skip to main content
Freelancing After 50

Freelancing After 50

By Paul Chaney
Freelancing After 50 is a podcast for people aged 50 and older who want to consider freelancing as a "second act" career, either part- or full-time, or who are already freelancing. We interview over-fifty freelancers, letting them tell their story, and get advice for freelancers from experts in marketing, finance, tax, legal, and related fields.
Where to listen
Amazon Music Logo

Amazon Music

Apple Podcasts Logo

Apple Podcasts

Google Podcasts Logo

Google Podcasts

Overcast Logo


Pocket Casts Logo

Pocket Casts

RadioPublic Logo


Spotify Logo


Stitcher Logo


Currently playing episode

Episode #2: Interview with Jay Thompson - Realtor, Freelancer, Fisherman

Freelancing After 50

Episode #10: Interview with Carol Alexander — Find Your Freelancing Niche
Carol J. Alexander, a freelance content marketing writer, is my guest on this episode of Freelancing After 50. Carol shares her story and talks about working part-time at first, the need to define a marketable niche, and the importance of self-care.  Carol offered this advice regarding finding your niche:  Make a list of all of your writing experience, everything that you've ever written before, whether it's an article, newsletter, or poem.  List your professional experience—every job you've ever held.  List your life experience: hobbies, things you do regularly, organizations you belong to, etc.   Finally, as a category for anything else you can think of—if you've won awards, been written up in the paper, things like that.  Once you get your list done, take two pens, a red pen and a blue pen. Go through your list and circle everything that was your favorite—something that you enjoy doing in red. Take your blue pen and circle the things you spend the most time doing.   Look at what's circled in both blue and red, and that's where you start.  You can connect with Carol via her website at or on LinkedIn.  My next guest is Robert Persichitte, CPA. We're going to talk about a subject that strikes fear in every freelancer's heart: taxes. I can assure you that Robert's insights and wisdom will allay your fears.  In the meantime, subscribe to this podcast—it's available on Spotify, Apple, Google, Amazon, and other outlets. Also, subscribe to the newsletter by the same name. You can do both by visiting the website, Freelancing After 50.  ~ Paul Chaney
September 28, 2022
Episode #9: Interview with Urban Adams, Investment Advisor: Managing Uneven Cash Flow
This episode is a particularly important one because it addresses a topic most freelancers deal with routinely — managing uneven cash flow. My guest, Urban Adams, provides information about that topic and the need to set aside funds for lifestyle planning, paying taxes, and investing for retirement.  Some of his primary talking points include:  Separate business and personal expenses to better manage cash flow. Give yourself a salary just as if you are a W2 employee. Set aside tax funds in a separate account and pay quarterly to avoid penalties and interest. Create a reserve for unexpected expenses and lifestyle planning.  Set up a SEP-IRA to invest for retirement. Connect with Urban via his website and LinkedIn.  Disclaimer (the legal stuff): Urban Adams is an Investment Advisor Representative with Dynamic Wealth Advisors. All investment advisory services are offered through Dynamic Wealth Advisors. Urban Adams also offers insurance brokering services; this is considered an outside business activity from Dynamic Wealth Advisors and is separate and apart from Mr. Adams’s activities as an investment advisor representative of Dynamic Wealth Advisors. Note: Freelancing After 50 is not only a bi-weekly podcast but also a newsletter. Click here to see the latest issues and subscribe. 
August 24, 2022
Episode #8: Interview with Samantha Anderl & Andrea Wildt, Co-founders of Harlow; the topic: setting rates
This episode is especially helpful because my guests, Samantha Anderl and Andrea Wildt, co-founders of the freelance business management platform Harlow, expertly address a topic that affects every freelancer at one time or another — how much to charge clients and what method to use: hourly rates, project-based pricing, retainer, etc.  They advise freelancers to: Get engaged with what others in your field charge to set a baseline; Figure out your goals, whether that's earning a six-figure income, having greater flexibility and freedom, or something else; Determine whether you can meet their goals based on the market's willingness to pay.  The pair also shares their respective freelancing journeys and what led them to start Harlow. It's 25 minutes of great conversation filled with valuable information that will help achieve more success in your freelance career.  Connect with Samantha and Andrea on LinkedIn.  If you like the podcast, please subscribe and share it with other over-50 freelancers. Also, check out the Freelancing After 50 newsletter. We publish it every two weeks. It's chock full of information to help older freelancers. 
August 10, 2022
Episode #7: Interview with Marcus Sheridan, Author of 'They Ask, You Answer'
Our guest on this episode of Freelancing After 50 is none other than Marcus Sheridan, internationally-known marketing expert and author of the best-seller "They Ask, You Answer."  Marcus shares his story of how the They Ask, You Answer concept came about and applies its principles to freelancers 50 and older.  Key takeaways:  Marcus says you have to be willing to do three things that other companies are not willing to do.  Talk about what others aren't willing to talk about.  Show (specifically through video) what others aren't willing to show.  Sell in a way others aren't willing to sell.  The Big Five He also listed the "big five" things you must talk about:  Price - How much does it cost?  Problems - What could go wrong?  Comparisons - We compare constantly to do our due diligence.  Reviews - Get customer reviews that talk about the good, bad, and ugly. Don't be biased.  Best - The top, the best, etc.  Marcus is very open to being contacted. You can reach out to him via his website or email. Also, connect with him on LinkedIn, Twitter, and YouTube. 
July 13, 2022
Episode #6: Interview with Ed Britton, the 'Not Retirement Rebel'
In this episode, I interview Ed Britton, a career and lifestyle coach who calls himself the "not retirement rebel." We talk about the retirement fallacies, why 65 is not the golden age for retirement, and what options people 50 and older have.  Ed lists three "passion pursuits" of not retirement people: Adventure, Achievement, and Contribution. He also discusses four stages of retirement:  Planners - those not yet retired but who are planning to Seekers - newly retired who don't know what to do with themselves Over-ready - people who have been retired for a while and know retirement isn't all it's cracked up to be Cut loose - individuals who were forced to retire due to layoffs or other mitigating factors Lastly, he shares four "ambitions" of people with a not retirement mindset: Contribute (to family and community), Cause, Personal Development, and Income Generation.  We focus on the income generation ambition and talk about it can be interwoven with the others.  You can connect with Ed via LinkedIn and his website, 
June 29, 2022
Episode #5: Interview with Rob Ainbinder - How to Manage Your Freelance Business Growth
In this episode, I interview Rob Ainbinder, a digital marketer, author, investor, and foodie. (Disclaimer: We talk BBQ at the beginning. That's one of Rob's passions.) He is also CEO of Why People Click, a digital marketing agency that grew from his early freelance beginnings.  The topic is this episode is how to manage your freelance business growth. Rob shares his own freelance growth story and offers practical advice for other freelancers, particularly those aged 50 and older, on steps to take as your business grows. He discusses branding, how to choose a domain name, the importance of networking, and other pertinent information.  You can contact Rob by visiting his website, Why People Click, or via email: 
June 08, 2022
Episode #4: Interview with Leslie Tayne, Esq. on Why Freelancers Need to Use Contracts
Leslie Tayne is an award-winning financial attorney and the founder and head attorney of Tayne Law Group in Melville, New York. She is also the best-selling author of Life and Debt: A Fresh Approach to Achieving Financial Wellness and an expert in legal matters related to entrepreneurship.  In this episode, Leslie discusses why freelancers should use contracts, what elements to include, and the risks of not having one. She also talks about steps freelancers can take when clients don't pay in a timely manner and why you should not use templated contracts but work with an attorney when constructing one.  Her main point: Freelancing is a business and should be treated like one. That includes the use of contracts.  You can connect with Leslie in the following ways: Website: Tayne Law Group Twitter: @LeslieHTayneEsq TikTok: @lesliehtayne (631) 470-8204
May 25, 2022
Episode #3: Interview with Jane Genova, Veteran Freelancer & One of the Smartest People I Know
Jane Genova has been freelancing longer than many people have been alive — 35 years, to be exact. We pack as much of her experience, wisdom, and advice in this episode as possible.  Jane shares vignettes from her long-tenured career. She also describes how she deals with marketplace age bias and talks about her "reset" — shifting her services and mindset to fit prevailing marketing forces — and offers sagely, yet practical advice to older freelancers on what to do when, in her words, you "fall off a cliff" in your career. (We also talk about how she doesn't view freelancing as a "career.")  The chief takeaway: Rely on your network of contacts. That's where the work will come from.  You don't want to miss this delightful and informative 15-minute conversation.  You can get in touch with Jane via email. Her address is To learn more about Jane, visit her LinkedIn profile and read her legal blog, Law & More.  
May 11, 2022
Episode #2: Interview with Jay Thompson - Realtor, Freelancer, Fisherman
Jay Thompson retired from the real estate industry at age 57 and headed from Seattle to the Texas coast to fish for marlin. It wasn't long before he realized that as much as he loved it, fishing wasn't a full-time sport and that he needed to "unretire." So, what did Jay do? Started freelancing as a B2B writer, speaker, and business consultant.  In this 20-minute episode, we talk about why Jay got into freelancing, the benefits he has gained, the challenges he has faced, and one piece of advice he would give others who are considering retiring and starting a freelance career. Key takeaway:  According to Jay, the key to successful freelancing can be summed up in one word: confidence. "You've got to have the confidence in your ability to get the job done ... I won't say anybody can do freelancing; it takes a certain mindset. But having confidence in your abilities is really, really important." You can reach Jay via email at 
April 20, 2022
Episode #1: Interview with Amie Chaney, My Wife and Freelancing Partner-in-Crime
In this, the inaugural episode of Freelancing After 50, I interview my wife, Amie, a legal assistant, who shifted back into freelancing after many years working in law offices.  In this episode, she shares what motivated her to move back to freelancing, the benefits and challenges she has experienced so far, and one piece of advice that every over-50 freelancer ought to know. 
April 06, 2022
Welcome and Introduction
I’m Paul Chaney, a freelance B2B writer, editor, and digital marketer. I want to introduce you to a new podcast, Freelancing After 50. It's tied to a blog and newsletter by the same name.  The podcast will feature stories from people 50 and older who decided to become “greypreneurs” by starting a freelancing career. Call it a second act, encore career, or simply breaking the bonds of the corporate grind to do something they love that gives them freedom, flexibility, a newfound sense of purpose, and the prospect of making more money than they ever have. I’ll also feature interviews with subject matter experts, people in finance, legal, marketing, and other fields, who can provide practical advice freelancers need to know. I plan to publish a new episode once every two weeks. Subscribe to the podcast, so you don’t miss a single one. Join me and my guests as we discover the joys of Freelancing After 50.  ~ Paul  PS: Did I mention that I’m 66 and have been an over 50 freelancer for nearly 10 years. 
March 30, 2022