#052: Overlooked Freelance Writing Opportunities for Retiring Boomers

This is a YouTube video titled "#052: Overlooked Freelance Writing Opportunities for Retiring Boomers" featuring a podcast episode hosted by Ed Gandia. The episode includes an interview with Kathleen Fink, a retired professional who shares insights on how baby boomers can leverage their writing skills and passions during retirement to find fulfillment and meaningful freelance opportunities. The discussion covers topics such as the benefits of passion-based writing, overcoming age discrimination, finding freelance gigs, and maintaining a balanced, low-stress pace in retirement writing work. The content is from July 24, 2025.
Welcome to the High Income Business Writing Podcast, helping you propel your writing business.
To a whole new level. And now, here's your host, Ed Gandia.
Well, hello everyone and thank you for joining me for episode 52 of the High Income Business Writing Podcast. My name is Ed Gandia and this is the podcast for business writers and copywriters who want to take their writing businesses to the six figure level or.
The part time equivalent.
As a quick reminder, you can find detailed show notes to this episode by going to b2b launcher.com episode 52 so I'm doing something a little different in this episode and I'm exploring a topic that's less about achieving a high income level and more about achieving fulfillment in your business and in your life. And the premise of this show, and really my general approach to freelancing, is that earning more and less time should be one of your key drivers. It should be one of your main goals, because it's that kind of progress, when done in a spirit of balance, of course, that enables you to have more time, more freedom, and live a richer life without sacrificing your income. You know, we tend to look at this income thing as a trade off, and I've always argued that it does not need to be a trade off. I think it's the wrong model, that's the wrong approach. You can achieve both. You can have a high income level, have more freedom and flexibility in your life. However, there are times when optimizing your income is not necessarily the best goal. You know, this earn it more and less time model is not for everyone. And I admit that in it might be for a lot of people, but sometimes it's just not the right model, not the appropriate model in every situation or in every stage of life. You know, you move through different stages in your life and sometimes there's a different model that works best. And that became very apparent to me when I was approached recently by one of my listeners, a freelance writer by the name of Kathleen Fink. And she pointed out a different take on my model. And it's really one that can work especially well for retiring baby movers, those who are already retired and those who are already thinking about retirement, who are approaching that retirement age. And rather than making income, the focal point, what Kathleen has done is she's found great joy and fulfillment in pursuing writing assignments through her passions. She's found that there's an amazing opportunity right now for boomers who are approaching retirement age or already retired, who have great skills, knowledge, experience and perspective that could be put to use in a really useful and profitable way, but profit not being the main driver, the main goal. And in this episode, she's going to share some great insights and ideas that may change the way you view retirement. Now, obviously this is extremely relevant for those of you who are approaching retirement or already retired. But, you know, I think everyone will find some nuggets here. I think don't skip over this because you're 35 years old and you don't think this applies to you. I think there's some really valuable lessons for just about everyone. So with that, let's go straight to the interview.
Hey Kathleen, welcome to the podcast. It's great to have you here.
Thank you. I'm very glad to be here.
So why don't you start by telling us a little bit about yourself and specifically your background, your experience with writing and so forth.
Well, I actually have done over 20 years of project management experience in financial services. And, and I didn't really realize this at the start, but that involves continuous writing. I started writing project plans and issues lists and strategic visions and all kinds of customer documents and training documents. And I also, by the way, useful for writing, researching, developing networking skills, that kind of stuff. So I did that for many years in one continuously changing merging organization with many different cultures. So that was not something I saw as a transferable skill. However, even back then when I was incredibly busy focusing on that kind of thing, I went to the editor of a Japanese garden design magazine and said, hey, would you be interested in writing an article on this? I'm interested in the subject. And he turned the tables on me. So I started writing articles on Japanese garden design and tea ceremony and did one or two a year for over a period of 10 years, even while I was being a project manager. Because I have a very strong passion, I have quite a few of them. But one of my strong passions is Japanese gardening in the tea ceremony. And that was incredibly satisfying. That was even a volunteer job. I wasn't paid for it. I didn't care. I was in this forum of English speaking folks who love Japanese gardens and tea ceremony and I could actually communicate that way. Now people do it via blogs and Internet groups and stuff very much more efficiently. But back then it was quite a treat to be part of that community.
Sure. And we do have listeners in Japan, by the way, so that's really cool. And I lived there for three years. I lived in Okinawa, so I'm familiar with the tea ceremony. It's a beautiful thing. It really is a beautiful culture.
Yep. So that I knew there was more to life than one job. I had other things in my life that mattered to me. So when I was laid off from the banking world, as were so many people, baby boomers and others, I started learning about job hunting as an area of passion, which it still is, joined job seeker networking groups and decided that I was going to have time and thank goodness to work on some other things I love. So I also collect beautiful rocks and I went looking for an article about one of the types of Jasper that I collect and there wasn't one. So having written all these articles about Japanese gardens, I said I'm going to write that article. So I actually went out and bought myself a camera with super macro capability, learned how to use it, got the writing guidelines from another hobby magazine, learned how to do that and just decided that I'm going to do it. And I took my time and I went through it and I started getting articles published while I was, you know, doing that and some other things, learning how to counsel people who are job hunting and that kind of thing. So that was fun. I did that for a while and then I discovered I wasn't probably going to get a job in banking again. So I did a detailed self assessment and out of that a lot of different factors told me that what I really wanted to do was to go freelance. And that was not in the context that was back in 2008 and it was. I wasn't in the generic. I mean I'm very much part of the trend, but I was not aware that I was part of a trend that there's so many people that have decided they can't get a job in the conventional way so they're going to go freelance. So I was out there doing it. And my little business is called Expressive Projects. It involves writing, photography and garden design. And I just started writing on all kinds of things. I continue to write about rocks and gardens and tea ceremony I picked up. I also love music and I sing. So I did a concert series and do PR work. I write about gardens and the arts and how that supports, well, being some crafty things, shadow boxes. And now I'm moving into a focus on wellness and how we can all improve our health by taking responsibility for that. So that's a little background on me. But I've always been communicating via writing. But I had no idea I could write about my passions and make that the focus of what I do.
So just so I make sure I understand here, the writing you do is this for a blog that you publish? Or is it for a combination of maybe a blog and some publications where you have your articles placed? Tell us a little bit about that.
The type of writing. Sure. When I write about rocks in Japanese gardens and tea ceremonies, I'm doing that for specific published magazine entities. I do PR for a couple of musicians, and that goes out on the media online as well as in hard copy print media. And in writing about the arts and gardens and that kind of thing, I get to 10 conferences for free and I write up coverage for the conferences, which gets published out online. I don't have a personal blog. I link some of that to my LinkedIn profile. Eventually, I may stop doing the actually writing enough to get a blog up and going. But so far I have found that I have no problem finding other people's blogs or other ways of publishing without even having to have a website or a blog of my own, Interestingly enough.
Gotcha. Okay. No, that's, that's, that's really neat. And so it sounds like you have a variety of clients, different media, and that's actually a good segue to my next question because really what we're talking about today is using your writing skills in retirement. Whether you suddenly find yourself retired because you've realized that you're not going to go back, or this is a planned retirement, now you're looking for some way to use your, your talents, your skills, your passions, and, you know, you and I communicate. Gosh. We got in touch, what, a couple of months ago. We've had kind of an interesting conversation via phone, via email about the amazing opportunity right now for baby boomers who are either retired or approaching retirement and are trying to figure out how they can leverage those talents. So tell us a little bit about that because you've done a lot of thinking and research in this area.
Yeah, it's really an amazing opportunity. There are about 76 million baby boomers who were born between 1946 and 1964, and a quarter of them, that was a quarter of the total population in 2006. Over 50% of those have a college education and they started retiring in 2011. Now, many boomers are not retiring because they need the income or they don't need to. They're doing stuff they love and they just keep doing it. There are a lot of those lucky folks, but there are also a whole bunch of people, and again, I'm very interested in the whole employment thing and what's going on in the world of work who are overstressed and unhappy in their work and some of those boomers have stepped down from high stress jobs and taken lower stress ones or changed their focus a bit, or are now doing part time or even portfolio careers that involve maybe three or four different skill sets cobbled together. So there are lots of people and then the lucky ones who can afford to actually stop working. But within that resource pool, there's a huge amount of experience, bandwidth and energy. People are have a lot of energy. I count myself among them. I'm in better health than I was 20 years ago, so I have a lot. I don't want to retire in the sense of being, you know, not doing something that's meaningful to me. So. And many of these folks, like me, didn't realize that they have writing skills that can be put to good use, both for their own benefit and to benefit others. And there's no end of worthy things to write about large and small if they don't have a lot of personal passions like I do. There are enough key issues locally, nationally and globally that can use people who can apply their experience and wisdom and perspective and time they may have to dig in. So I put it this way, that writing skills plus a little bit of leisure, maybe not full time leisure, plus some kind of passion or interest, can actually be turned into or equal personal satisfaction plus making a difference. And there's a whole cultural shift on this. Arianna Huffington has just published a book called Thrive, which has her new definition of success, rather than burnout in corporate America is to focus on, well being, wisdom, wonder and giving. And all of that kind of motivation of including lifestyle issues first and then being able to have the time to really do some of the things that are a little softer, that take some exploring and maybe some openness to what you're really feeling, and then being able to help others. That's an incredible opportunity for boomers. This generation may be the last in a while that will have the luxury of applying a certain amount of resources and leisure to their retirement years. Because of some of the challenges that the globe's facing and economic challenges and all of that, many people like myself were able to work for the Same company for 20 years and have a retirement of sorts already saved. So that group is in a position to provide, whether at a local level or whatever level, it is a huge amount of benefit to this world we live in as well as to themselves. So there's just, there is a huge opportunity here.
Well, and let's talk a little bit.
More about those benefits because, you know, obviously most of what we talk about in this podcast is really the income part of it. And the idea is not that money is the only thing to go after. The premise is, look, if you can boost your income to a certain level, then that opens up a lot of doors. That opens up a lot of freedom and flexibility. But I think there's another side to that that's kind of implied in the message that I put out there that you really bringing to the surface here. And I'm. And I appreciate you doing that, which is, you know, there's a flip side to that, especially if you're in a situation like you are. Tell us a little bit more about the benefits of pursuing these kinds of passion based writing opportunities during retirement.
Well, what hit home for me a number of years ago, I read an article about this book written by an Australian nurse, Bronnie Ware, called the Top five Regrets of the Dying. And she found, he found was a wish that they lived a life that was true to themselves. So you may not like, you know, myself at 65, facing a window of retirement, I can't go back and become a, you know, brain surgeon or something like that. What I could do is become educated on some aspect of how the brain works and write from my own individual perspective and experience. A pretty interesting article on the topic. Just kick that out of the air. But there's an opportunity in retirement to actually get into some of this being true to yourself on levels that you might not have been able to do when you were trying to earn a living in a dog eat dog world at very low risk and at low stress. So whether you use the Internet or even write a private letter to family members you haven't been in touch with for a while, that kind of writing from the heart, which involves your true self, will create something that I think is amazingly powerful called synchronicity. And that means is that resources find you because you're sending out a vibration that says that you have meaning around the subject and you just start radiating around that subject. And resources say, wow, you know, you have something interesting to say. Or you know, I every time at one point it was amazing because huge and enormous projects where I could make a contribution with my writing found me. And I'm just saying this is very exciting and to segue into it, I mean, one of the interesting things about retirement is that writing suits a variety of lifestyles and energy levels. If you want to stay home and you can do a lot of research from your computer online, you can use the phone, you can do a lot of writing in that way and stay in local circles, or if you love traveling and you want to go out and meet people and do all kinds of fun things out in the world, you can continue to write while you're doing that. Almost any lifestyle can adapt to this. So that's a really interesting thing about it. And a lot has been opened up by the new world of the Internet and computer connections. But more importantly, in terms of personal satisfaction, happiness is a lot about meaning. And can you make a contribution that has meaning to you and to others? And writing can really do that. Even a small piece, even a comment somewhere on someone's Facebook page that, you know, points them in a direction. It's amazing. And writing has such power at whatever level. So you can create satisfaction for yourself by the writing process itself, which is, you know, creative play, developing and trusting your intuition, experiencing flow where you lose a sense of self, you're so into what you're doing and you can build all kinds of connections. And these are all soul feeding activities. I don't say that these are foreign to people who are writing for a living. But when you can do this around something you absolutely care about, where you're choosing the horizontal and the vertical and the subject, and you're able to take your time, time about it and really say, now what do I really sense about that and who do I want to call to check that out with? That's really soul feeding and all of that's possible through writing. So it's really powerful.
Yeah, I can absolutely see that. And you're right. And what you're doing is you're taking, you know, this is something that if you've been writing for a while, you already have hopefully experienced that many times. But here's an opportunity to, to really do more of that, right? To have more of those moments. And I'm going to switch gears on you a little bit in terms of some of the opportunities out there. And I want to talk a little bit more about what's available, where people who are in this situation can start looking and how they can start thinking about this. But one of the things that I hear a lot from people who are in their 50s and 60s, and I got a lot of listeners in that age bracket, especially those who have experienced age discrimination in the workplace. They're afraid that they're going to find the same discrimination when they retire and they start freelancing and they're looking for freelance writing opportunities. What are your thoughts on that?
Well, my general thoughts about that is, and I really found this to be the case that being older can be an advantage. And there's a couple of reasons why that's true. First of all, older people tend to have some kind of subject matter expertise or experience that they can bring to the table, which in the context of writing, where the product delivery that you're producing is something with a lot of face validity, the fact that you can do that and that you have something to say and you have a perspective can be very valuable. The other thing that I think is generally true, and I don't mean to be prejudiced against, against the young people with great writing skills who are incredibly good at it and very, very careful and reliable. There is, I don't know, a prejudice out there which can work to our advantage. That old school can mean careful, reliable, and often that you're a better writer. And I think it's really important that you do write in a very professional way and make all your communications highly professional to maintain that image. I'm very careful to use subject lines that are very clear in all my email communications. Follow the writer's guidelines, put out reminders at the right time, ask questions politely, all those kinds of old school things, but that can work to your advantage. The other thing about the kind of writing that I do, much of it's at risk. So when you don't have to earn a complete living doing it, you can go out and write. You can say, are you interested in an article on this? And the hobby magazines in particular, the kinds of things I started with, are fine with that. So they say, sure, you know, we can't tell you whether we'll accept it, but we like your topic and here's the guidelines and all that kind of stuff. So you go out there and you work with them, and they'll often help you because they want articles from readers who have some kind of hobby interest. They'll work with you so that you get it right. And then after that, if you do two or three articles, they're begging you for articles. So that helps. So that at that point, what's happening is that you've got the experience because you have a passionate interest in it. And because you're a little older, they assume you've been doing it for 10 years, you may have been doing it for six months. But, you know, that's a good point.
I never thought about that.
Right. And then the other thing is that I think that passion and networking and networking and timing trump age in a lot of this. Because if you really do your homework to find out what your true Passions are people are, you know, people who share your passions. And many of the editors do or the sources where you're going to be writing. That's what radiates the energy in the youth. It comes through, you know, you can hear it in my voice. So, I mean, if you really love something. For instance, my composer, musician, client hired me on the base of PR that I did on a volunteer basis for a concert fundraising series. And I just called him up and I said, I'd like to, you know, run a few sentences by you that to me describes your music and sight unseen and like almost immediately said, I'd love to hire you to do all my priorities. I said, okay. He had no idea how old I was. And he's a really charming human being and we have a delightful relationship. And I've been doing his PR for two or three years now.
Is he about your age or is he younger?
He happens to do kind of a jazz, rock, fusion type of sound. And he is, I'd say, maybe in his 50s. Okay, so he's one of us. But having nosed around in that world a little bit, there are, if, you know, if you have, if you're knowledgeable or passionate about any particular type of music and get out there. I don't think, you know, I think it would be kind of amusing to people if you're older and you're an absolute expert and totally enthusiastic about the latest music rage. They love it.
Yeah. Yeah, that's very cool. Very cool. So let's talk about some of what you just mentioned, which is opportunities. You know, you. You talked about how you found one of these opportunities. How easy is it to find freelance writing opportunities and of the nature that we've been discussing here that are a lot passion based and where would you look? What are some ideas there?
Well, first of all, don't ignore the possibility for barter. I was really surprised how possible that it is. Like I said, I get into free concerts with all those, you know, the concert series of my musician. There's sometimes shops who would like some help with, with some pr. I've written and used photographs for an incredible bed and breakfast in that I just adored. And I've, you know, gone online and done reviews for them and stuff like that. And I've gotten three days of free nights at the place, actually. Wow. Yeah, really nice. There's barter opportunities for people who, you know, make a relationship and this is all relationship based. And then there's some boomers who may be friends of yours and they have amazing stories or they have, they need some custom work done. And so you can do that. There's academic conference coverage. There's amazing things. Hobby magazines I've mentioned, nonprofit and religious groups are often looking for volunteer opportunities. One of the little things that I do because I just enjoy doing it is I write up new member brief articles for the newsletter for my church, you know, and they're great and I get to know people. This just takes 15 minutes. So you creating and then the local newspaper and I actually managed to finagle away my way into healthcare Journalist conference in Boston recently and some of the strategies you can finagle an article on a subject of some interest or depth if it has a local touch, but having nosed around in that world a little bit, there are with your local newspaper, which can provide a first step into other journalistic opportunities because you can use that copy and you can create links to the copy or you can. There's many different ways to create community around a subject as well. So letters to the editor if you know, if you have, if you're knowledgeable or passionate about any particular type of music and get out there. I don't think, you know, I think there's comments on LinkedIn or Facebook groups, Amazon reviews. There are many. I have several friends who are writing books as I speak and I usually talk to them and I say, you know, I really like what you're doing. I'd love to write an Amazon review for you in exchange for a copy of the book. They're another kind of barter because I care about the subject and you know, you can. There's ways to create community remarkably quickly with people who are really out there and high up in the field by getting out there on some of these LinkedIn, you know, communities or even Facebook, you know, pages that people have out there. And you have to follow up, you know, say, can I get in touch with you afterwards and follow up on this conversation? It's been so fascinating. And out of that can come a writing project very easily. But there's usually if you find a passion or an interest and I've just talked about some of the things that I've been doing, there's a way to write about it and so you can volunteer with the team that's. I mean, I did an incredible project with the team that was trying to take a healthcare problem that was little recognized, misunderstood and disguised itself as obesity in women, but isn't cured by diet or exercise. And there's a whole incredible project around that. And I volunteered to help out with copy on webinar, PR and that kind of thing. And there's a whole international team going off and making change that will help millions of women worldwide and is already making incredible progress. So there's no limit to the opportunities that will fall in your lap if you keep following what you're. What you really care about, what motivates you, and just look around a little bit and be a little creative. It's out there.
Well, I can't emphasize that enough, and you can't emphasize that enough. It's this whole issue about passion. Right. Because much of what you talked about here we've addressed in other shows, but where most of the time, I would say it has a business, a pure business land to it. But, you know, you mentioned, just take an example, commenting on LinkedIn groups or somebody's Facebook page. It's very different if you. If you just tell them, oh, I thought, you know, your stuff was really interesting, which may or may not come across as authentic, but if you have a real passion for, like you said, Japanese gardens, and you do the same thing on a page that has to do with that, it takes a whole different meaning. Right. And it comes across very, very differently than it does if you're just throwing it out there. It's like, oh, that looks nice. You know, let me see if I can maybe start some dialogue with this person.
Yeah, you can have so much fun with it. I was on a. Be kind of amusing to people if you're older and you're an absolute expert and totally Healing Gardens LinkedIn group. And I talked about somebody had little video enthusiastic about the latest music rage. They love it.
Yeah, yeah.
Oh, of a fountain. I said, well, what if you put colors and music in there? And it all varied depending on what was going.
That's very cool. Very cool. So. So let's talk about in some of what you just mentioned, which is opportunities, you know, you talked about how you found one of these opportunities, how we.
On with the sounds around and birds and all that. And we went off and had a lot of fun with that idea with all these experts, you know, people who really do this stuff. I'm just. I'm very enthusiastic about using gardens for healing as healing space. But this is an opportunity for me, who has a deep passion but not any professional credentials, to talk to people who are out there really doing it. Yeah. And it was amazing.
Yeah. I would add that, you know, many times if you find books that are about to be published on the topic that you're interested in, and I'll tell you right now, those authors are very, very interested in engaging in interviews and getting blog posts written about their work, whatever. And if you're sincere and authentic, easy is it, to find freelance writing opportunities and in your passion about the topic and you approach them that way without sincerity, let me tell you, you have an immediate, a captive audience there with that author because he or she is trying to get publicity for it. So, you know, that's an opportunity right there to establish some dialogue and possibly start a relationship with that individual.
Right. And the same kind of thing holds for say, you know, a local gallery or I don't know what your thing could be a sports team or anything. If you have a particular personal appreciation. That's I'm a lot about, you know, if I were to say about me with all my passions and stuff, I have a gift for appreciating things. And if you can show that, that you really get what they're doing and that you can convey that to their customers or to their family or whoever the target audience is, that's an immediate opening for writing about it.
Well, tell me a little bit about the pace and what that's like. I mean, is it as crazy as it is in the corporate environment? Because that's the world that I kind of came from and that I work in. And I ask that because I know that many retirees or people who are looking already towards retiring in the next few years don't really want to go full tilt and just be meeting, having to meet crazy deadlines all the time. So tell us a little bit about that.
Well, for me, it's one of the most remarkable things about this little business that I've set up for myself is that I have the time to breathe and to explore new things. The pace can be quite relaxed. It does require some discipline. I have worked on a number of writing projects that went over years or months at a very kind of low key pace while various issues came together and other things were happening in between. And then there was kind of a push at the end to get the copy together and actually get it done. At a certain point you've got to sit down and really focus and edit and pull it together and meet all the guidelines and you know, of the.
Nature that we've been discussing here that are, you know, a lot of passion based and where would you look? What are some ideas there?
Well, first of all, my concert series does have deadlines and you know, my client does. But unless it's an event, it I can generally even negotiate I just worked on an article that somebody found me and said will you write about this new Jasper I discovered? I said be happy to. It sounds like fun. And we've been working on that a number of months. Don't ignore the possibility for barter. I was really surprised how and there was no deadline involved and we negotiated that it was. We were not going to be able to do a particular deadline because he's a farmer and he was out needing to do farming things for a while. So all of that is like really nice. It's like a totally different world. You can write shorter pieces that involve a much smaller commitment. I've written 20, 25 page documents for certain purposes but the shorter pieces are often more publishable because they pay less for them. For one thing, they can be quite low stress, low risk. And as I said, deadlines often don't apply. And what that means is you have time to do. I mean like I have all these things that I'm writing about are my passions. I'm actively doing a lot of things around those passions. But I have and exploring new ones by the way because that's just me. But I can research a topic without stress. I can talk and really listen carefully. I usually find that my writing changes based on interviewing people and I hear it with. With my heart and my emotions. And then I read the target publication. I get to know it well enough I may have a target public.
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