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I Stopped Job Searching at 55 — Here's What I Found Instead
24 Plays1 month ago
Are you over 50 and wondering what comes next — after the layoff, after the grief, after the job search? This episode changes the conversation entirely.
In this pivotal episode of the Ageism Survival Guide, we zoom out from the job hunt and reveal the full map: four powerful paths that experienced professionals over 50 can take right now — whether you've already lost your job or you're smart enough to be preparing before it happens.
This isn't about settling. This is about discovering that the best chapter of your career may still be ahead of you.
🗺️ THE FOUR PATHS WE COVER:
① Stability & the Feeling of Employment Remote work for seniors, part-time jobs, seasonal bridge work, government and nonprofit roles, returnship programs, and community-based opportunities. Because belonging somewhere again matters — and there are more doors open than you think.
② Entrepreneurship & Taking Some Risks Fractional executive roles, independent consulting, freelancing after 50, small business ownership, franchising, and building digital income streams. For the person who's done asking for permission.
③ Rewarding Personal Growth Encore careers, creative reinvention, monetizing your passion, advocacy work, and portfolio careers. For the person who senses that this disruption might actually be an invitation.
④ Teaching, Instructing & Passing on Knowledge Adjunct teaching, corporate training, online courses, executive coaching, mentoring, and content-based education. Because your wisdom is worth more than you're charging for it.
📚 RESOURCES:
🔗 AARP Encore Career Research: https://www.aarp.org/work/job-search/age-friendly-jobs/
🔗 Join our community on Discord: https://discord.gg/rrdaq48xJ
💬 Which of these four paths is calling to you right now? Drop it in the comments — I read every single one, and your answer will help shape which episodes we do first.
🔔Subscribe and hit the bell — the next 20+ episodes go deep on each opportunity. You don't want to miss what's coming.
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Transcript
Is job loss a chance for reassessment?
00:00:00
Speaker
Hey, stop. Before you send one more resume, you need to hear this. What if the job you're desperately trying to get back isn't actually the best thing for you? What if the loss of the job, as painful as it was, was the slap in the face that you actually needed to get on a different track?
Impact of job loss and modern challenges
00:00:25
Speaker
We've been through a lot together on this channel. If you've been there from the beginning, then you know that we started the journey in a very real and difficult place. The moment that the job that you counted on suddenly wasn't wasn't there anymore. Maybe That was a layoff. Maybe it was a forced retirement. or Maybe it was a, oh, we're going in a different direction conversation that left you sitting in your car, staring at the steering wheel and and wondering what the hell just happened.
00:01:03
Speaker
We've talked about the the grief because it is grief. It's a loss of identity, it's a loss of structure, it's a loss of sense of purpose and a sense of having to be somewhere, to to do something, a loss of contributing.
00:01:23
Speaker
We talked about age bias and hiring, those algorithmic resume screeners, the the hiring managers that look at your graduation date and don't bother reading past that on your resume.
00:01:39
Speaker
We talked about how to how to fight back, how to how to rebuild, how to re-enter the job market that has changed so dramatically, where AI is literally flooding the zone with thousands of applications for each and every job posting, and where the the old rules just don't apply any longer.
00:02:03
Speaker
Did
Alternatives to traditional job search
00:02:04
Speaker
it work? Well, it matters and and if you're still at that stage you're still job hunting and and and and you're still in the thick of it keep going those episodes on the resumes and the linkedin and stuff they're not going anywhere i'll continue to have your back but today we're going to do something really different really different today we're going to talk about what's possible what you may not have thought about before but
00:02:35
Speaker
Before we get started, I really want you to hit the subscribe button so that you can be on board for the entire journey because the journey is really just beginning.
00:02:50
Speaker
Here's the the truth that I think gets buried under the the stress of job searching. People over 50 are sitting on ah on a mountain value.
00:03:04
Speaker
Decades of of of hard-won experience. you know Real skills. Perspective that that only comes with actually doing things. Not just reading about it or or watching it watching a YouTube video about them.
00:03:21
Speaker
the The ability to to stay calm about everything. because Because you've been in fires before. The wisdom to to know what actually matters.
00:03:33
Speaker
to separate the wheat from the chaff. And here's what I've been thinking. What if the traditional job search, the resumes, the the applications, the interviews, the the waiting, and that rejection is only one of the paths that are available to you? What
Remote work and flexible options
00:03:54
Speaker
if the what if the best path is not the one that you're on right now?
00:04:02
Speaker
Over the next series of episodes, we're going to explore four major categories of opportunity, four paths that that people in in your situation, experienced, talented, 50-year-old at a crossroads, are taking right now.
00:04:20
Speaker
Decisions which I have taken over the last six years. Some are finding new stability. Some are building something of their own for the first time. And some are discovering who they actually were meant to be. Maybe not nine-to-fivers.
00:04:39
Speaker
And some are realizing that the most meaningful that they can do is to pass on what they know.
00:04:50
Speaker
So, there are four paths. Let's walk through each one of them. The first path is for people who say, I'm not ready to blow up everything. I feel like I just want to belong somewhere.
00:05:06
Speaker
i want structure. i want a paycheck, but I still want to feel useful. there's There's nothing wrong with that. Nothing at all. don't Don't let anyone tell you otherwise.
00:05:17
Speaker
This path is, it's more about stability. It's that that feeling of employment and it's that feeling that there are you know options out there more more than you might have realized.
00:05:30
Speaker
Let's start, for example, with remote and flexible work. Remote work, it didn't disappear after the pandemic ended, it it just transformed. There are entire ecosystems of remote jobs in in customer service, in project coordination, administrative roles, sales, account management, and even tech support.
00:05:51
Speaker
These are real jobs. They're full-time. They're part-time. They can be contract, and they're across every industry. And here's the the beautiful thing, that remote work is that that one great equalizer where our experience, you know, if if we're performing well on Zoom, well, frankly, nobody's looking at your age.
Bridge jobs and temporary solutions
00:06:13
Speaker
They're looking at what you can accomplish. Next, this is a bit controversial maybe, there's seasonal, temporary, or bridge work. Maybe you're not ready to to commit to a full-time role. Maybe you're still healing a bit.
00:06:29
Speaker
Bridge work could possibly be the answer. There's things like seasonal retail, tax preparation, which is hugely in demand. It could be tourism and and hospitality services, event staffing, short-term contract roles that that let you keep your foot in the door as you're trying to figure out what's next on your terrain map.
00:06:54
Speaker
I want to say something pretty directly about this. You know, taking a bridge job, it's it's not a step backward and it could actually be a strategic move that keeps your income flowing, it keeps you connected, and frankly often it could lead you somewhere that you didn't expect. It it could put you on a fresh new path.
Exploring government and non-profit roles
00:07:14
Speaker
Another maybe unexpected one is government or non-profit or mission-driven roles. This one is probably underrated and i mean, really wildly underrated.
00:07:28
Speaker
Local government agencies are are constantly hiring nonprofits. They need experienced leaders. They need grant writers, community outreach coordinators and and program managers. and And they tend to value experience rather than to penalize it.
00:07:45
Speaker
Another is workforce development roles, which help other people do exactly what you're doing right now, which is to grow rapidly into something new.
00:07:57
Speaker
And here's the emotional piece that that I want you to hold on to. These roles, they often come with ah with a a sense of meaning that the the corporate world just couldn't deliver.
00:08:09
Speaker
When the work matters, it changes your attitude and you show up different. Then there's something called returnships and career re-entry programs.
00:08:22
Speaker
Did
Programs for reintroducing professionals
00:08:23
Speaker
you know that that quite a few major corporations and an increasing number of medium-sized companies, they they have these um formal programs that are specifically designed to bring experienced professionals back into the workforce? I didn't know that.
00:08:39
Speaker
They're called returnships and think of them like like internships for people who already have decades of experience. and maybe Maybe it's a little bit similar to the Robert De Niro film, The Intern, but but without serving the coffee.
00:08:55
Speaker
You know, companies like IBM, and Amazon, Goldman Sachs, Unilever, this this is really a ah ah trend. And i'm going to probably dedicate an entire episode to this in the near future, because I think the opportunities here could be quite significant.
00:09:12
Speaker
And then maybe closer to home, there's community-based work. yeah You shouldn't overlook what's happening you know right right outside in your own backyard. There are are things like senior caregiving, childcare, pet sitting, house sitting, home organization and downsizing services, which by the way is a ah booming industry because, well, baby boomers are are really downsizing their homes right now.
00:09:38
Speaker
Sometimes the most stabilizing work is is actually the the most human work. The how do I say that the emotional promise of this first path, ah the thing I want you to hear the most is that you so you still belong, you still have a place and and you can regain stability with without having to go back to that toxic place in the corporate environment that was probably grinding you down anyway.
00:10:12
Speaker
Now, and ah I want to pause here for a moment. because i I can already guess what some of you are thinking, which is, hey that all sounds fine, but I don't want fine, John. I'm i'm tired of working for someone else's dream, and I'm i'm tired of being managed by by people half my age who never actually built anything.
00:10:35
Speaker
I want something that's mine.
00:10:41
Speaker
Good, because that is exactly where we're going to go next.
00:10:48
Speaker
Path
Entrepreneurship and freelancing paths
00:10:49
Speaker
number two is for the person who's done asking for permission. This is the the land of entrepreneurship and frankly taking some some calculated risks.
00:11:02
Speaker
And I want to be very clear about something. I'm i'm not talking about you know dropping everything, quitting, and and and trying to start the next Amazon. But I'm i'm talking about a big spectrum of ways to to build something that belongs to you from very modest starts all the way up to running your own firm.
00:11:25
Speaker
Okay, let's begin with consulting and fractional leadership. This is one of the most, um I would say, powerful and underutilized opportunities for experienced professionals. I've covered that in another video and I'll link to that here.
00:11:41
Speaker
Fractional leadership means that you bring your your C-suite or or other management experience to companies that that need it, but they can't afford to hire a full-time executive. So it could be fractional CFO, CMO, CIO, any of those alphabet soup. You work with multiple clients, you have your own schedule, and you charge what your decades of experience are actually worth. And that's not limited to the C-suite because there are also lots of positions similar to this that are available in the layers below.
00:12:12
Speaker
Independent consulting, it works in in very much the same way. You find things that that took you years to learn. Companies, they're going to pay you and they could pay you quite well for access to knowledge without the overhead of having a full-time hire.
00:12:28
Speaker
There are also advisory board positions, which are just another layer of this. Companies of all sizes, they need experienced voices in the room and one of those could be you.
00:12:41
Speaker
There's also ah freelancing and and and contracting. These are things like writing or editing or content creation, IT t and engineering design, HR recruiting, training development, research and analysis, virtual assistants. I mean, it's a long list of opportunities that you could leverage your expertise.
00:13:09
Speaker
Now the the gig economy, it gets a bad reputation and and yes, some of those are genuinely exploitative, but for experienced professionals who who know how to deliver, then freelancing can be enormously flexible and and also financially rewarding. the The key is just positioning yourself correctly and we're going to get into that 100% in one of the upcoming episodes.
Franchising and digital income
00:13:37
Speaker
Another alternative is small business ownership, a consulting firm, a tutoring or coaching practice, home-based services, online reselling, digital products, templates, guides, mini courses, things that that you can create and then you just sell them repeatedly.
00:13:57
Speaker
the barrier to starting a small business, frankly, has never been lower. um That's both a challenge and an opportunity. And we'll dig into what actually works for people in our demographic in future episodes.
00:14:13
Speaker
Then there are franchises. Franchising is, i would say, an underexplored path for experienced professionals, but it comes with um let's say built-in systems, brand recognition, and even support structures that you don't have to build yourself.
00:14:32
Speaker
For example, senior services franchises are growing fast given the demographics of the population. Other things like home repair, handyman services, cleaning and maintenance, fitness and wellness.
00:14:48
Speaker
you know The investment It can vary widely and it's absolutely something that that you need to put a significant amount of due diligence into but it could be a path worth understanding and looking into one can also explore micro entrepreneurship and um I guess I can call it digital income. This is the the world of of smaller scale digital income, things like affiliate marketing, print on demand, digital downloads, newsletters, YouTube channels, podcast sponsorships, online communities.
00:15:27
Speaker
And I want to spend some real time on this in one of my future episodes because there's a lot of noise in this space and and even a lot of misinformation that that's targeted at people in transition.
00:15:38
Speaker
i want I want to cut through that and explore what can actually be realistic. What's the emotional promise of of this path?
00:15:49
Speaker
Well, the clear one is that you can build something that's yours. you you you've You take back control. You generate income without having to ask anyone else for permission on what to do or how to do it.
00:16:04
Speaker
Before I get into the next two themes, and these ones I think are the ones that that personally mean the most to me, i want to ask you something.
00:16:18
Speaker
if If you're watching this and you think that, hey, this feels like you're speaking directly to me, well, I want to hear from you. you know, do me a favor, drop a comment below.
00:16:31
Speaker
Tell me which of these these four themes that we talk about today, these four paths, feel the most interesting, the most relevant for you. And that'll help me to prioritize which ones I'm going to cover because there are going to be a lot of episodes on each of the individual different opportunities that I discussed today.
00:16:50
Speaker
And if you haven't subscribed yet, Please do, because every one of these upcoming episodes, it's going to go deep on these specific opportunities, and I really don't want you to miss a single one.
00:17:04
Speaker
All
Pursuing encore careers
00:17:05
Speaker
right, let's get into path three, because this one this one is personal. It's the one that I happen to choose at the age of 56. There are a lot of people who, you know, reach this moment, the the job loss, the disruption, the the forced stop and and and something quietly surfaces that's been buried for a long time.
00:17:31
Speaker
Yeah, I'm talking about a dream. maybe Maybe you haven't thought about your dream for a while. You know maybe a different version of of yourself. You ask a ah question that starts with, what if I actually did?
00:17:49
Speaker
This third path, it's, I call it the rewarding personal growth. And and and it might be the one that actually changes everything for you.
00:18:00
Speaker
So let's let's talk about encore careers. An encore career, it's a second act that's driven by by purpose rather than just a paycheck.
00:18:13
Speaker
It's the ah the corporate attorney who becomes a non-profit leader fighting for housing equity. It could be a marketing executive that now is advocating environmental causes. It it could be a ah finance director who moves into healthcare care to to support various social services.
00:18:41
Speaker
All of these have have meaning. These are not retirement activities. These are are real careers and and and they're paid. and And those can also happen to line up personally with something that you care passionately about.
00:18:59
Speaker
You know, the AARP, they've documented this trend pretty extensively and and and willing to the research in the description below. It's really quite interesting to read.
00:19:11
Speaker
So how about creative and personal reinvention? You know, writing a book or or a memoir, starting ah a podcast, launching a YouTube channel. I've got two of those. Creating a community or a membership group around around something that you you that you really care about.
00:19:32
Speaker
There's also advocacy work. for ageism, for caregivers, for veterans, for for health care. and And those causes are exploding right now. They're people building movements around the the exact experiences that that feel like wounds. But in doing so, they're healing themselves while actually also helping others.
00:19:56
Speaker
You can try to monetize a hobby. Things like photography or woodworking, art and design, music lessons, writing or blogging, gardening, landscaping, travel planning. What else can you do?
00:20:13
Speaker
I have friends that went into each one of these different categories and they've had a really fulfilling second encore career ever since. These are not just side hustles. For many people, these actually become the the center. And yes,
00:20:28
Speaker
you can earn real money doing them. So we're going to look at some of the real paths for for doing this, not not some of the hype that comes around some of them, on how you can turn something that you love into something sustainable.
00:20:43
Speaker
And
Adopting portfolio careers
00:20:44
Speaker
if you if you can handle complexity, there are what I would call portfolio careers. This is for the people who say, I don't want one thing. I want a whole life.
00:20:58
Speaker
So a portfolio career, it's it's ah a deliberate mix. It's part-time work, consulting, and other passion projects. You could look at this as income diversification.
00:21:09
Speaker
it's it's ah It's a lifestyle-first design where you're no longer organizing you know your life around a job, but you're actually organizing your work around your life.
00:21:23
Speaker
This is something that that I chose to do, and I've been working a portfolio career for the last five or six years. And it's no surprise that that this is increasingly the choice for the most fulfilled people that I've encountered in conversations. The emotional promise of this path and And I want you to to to really hear this one, is that is that you can grow a new identity. You can turn the the pain of of this moment into a new purpose.
00:21:59
Speaker
You can become the person that you were always meant to be. And it might have taken exactly this disruption to get you to turn on to this new path.
Teaching and mentoring opportunities
00:22:14
Speaker
There's one more path. And in some ways, um I think it might actually be the most powerful one because it's it's not about finding, you know, your next thing. It's about realizing that that that you are the thing.
00:22:34
Speaker
What am I talking about? Well, the fourth path, it's it's teaching, it's instructing, and it's passing on what you already know.
00:22:45
Speaker
And I want to start this section actually with with ah with a question. how many How many times in your career did someone younger than you come up to you and ask formally or or informally, hey, can i pick your brain for for just a few minutes?
00:23:06
Speaker
I know I've had that happen to me a lot throughout my career. How many times were were you the person who actually knew how something worked when you were the one who'd seen it before? and and And who could look at a situation and say, hey, I know exactly what's going to happen if you go down that road because, well, frankly, you've already been down that road, right?
00:23:35
Speaker
That knowledge, that that wisdom, they hold enormous value. The question is just whether you're going to let it sit unused or whether you're going to put it to work.
00:23:50
Speaker
One avenue is is teaching and and training. You know, things like adjunct teaching at a community college or corporate training and facilitation. It could be something like online course creation on platforms like yeah Udemy or Teachable or Skillshare.
00:24:09
Speaker
It could be instruction in community programs. These are all accessible entry points, and and and many of them don't even require a teaching credential. What they do require, though, is that You have deep knowledge of a subject and you know how to explain it in a clear way that people understand.
00:24:32
Speaker
You've been doing that for your entire life. Then the other one is is perhaps coaching and mentoring. Executive coaching, career coaching, life and leadership coaching.
00:24:47
Speaker
This is, i would say, probably one of the fastest growing professional services sectors in the country, in the United States. Experienced professionals with the right frameworks and and training, well, they're uniquely positioned here.
00:25:04
Speaker
And the on the mentoring side, there are formal programs for younger professionals. This is increasingly being used by companies who are trying to bridge the experience gap that their own hiring practices have have created.
00:25:22
Speaker
Kind of funny how how that happens, isn't it? Having to fix their own self-created problems. And
Recap of career paths
00:25:30
Speaker
lastly, there is what I would call content-based teaching.
00:25:35
Speaker
So here we're talking about educational YouTube channels, instructional podcasts, workshops and seminars, maybe even writing guides, templates and how-to books.
00:25:49
Speaker
You know, we can talk about all of these specifically, um and we will, because many of you who are watching this channel are thinking maybe about launching your own program.
00:26:02
Speaker
and And there are things that I've learned, things that that I wish someone had told me before that i really want to share with you in the coming episodes. The emotional promise of of this fourth path, and I want to really leave this one ringing in your ears, is that it you have wisdom worth sharing.
00:26:25
Speaker
Not someday, but but but why not why not right now? you You can help to shape the next generation and and where where where they go.
00:26:36
Speaker
You can be valued, I mean really genuinely valued for for what you've actually lived and what you've learned, as long as you know how to pass that on.
00:26:48
Speaker
There it is, the the map of our terrain. Four separate, distinct paths. There are not four options where you you rank and you choose like ah like a multiple choice test, but these are four completely different directions. Each one is valid, each one is powerful, and and each one is capable of of leading you somewhere better than where you had just started.
00:27:15
Speaker
Let me just go back. There's path one, stability, for when you want to want to breathe, you want to belong, and and and and you want to rebuild your footing. Then there's path two. It's entrepreneurship for when you're you're ready to build something that that's all yours.
00:27:33
Speaker
Then let's go to path three, which I call personal growth. and And this is where the disruption is actually an invitation for you to become what you were actually meant to be. And lastly, path four, teaching and legacy. For when you realize that the most powerful thing that you can do is to share the knowledge that you know.
00:27:59
Speaker
Over the next series of episodes, we're going to dive deep into each one of these paths, really pick them apart one by one, subject by subject. yeah We're going to look at specific opportunities. We're going to look at at real stories. And we're going to look at practical steps that you can use.
00:28:17
Speaker
The things that actually work and the things, well, that that don't. Look, you've survived something hard, and and and that took real strength. But surviving, it's it's just the beginning.
00:28:36
Speaker
So what what comes next? That's the part that's going to get really interesting. Youth runs fast, but age knows the terrain.
00:28:48
Speaker
Don't forget it. Look, if this episode spoke to you, if these if these four paths, they they made they made something light up inside of you, drop something in the comments. I'd like to know which one, every single one, and I'll respond to your comments.
00:29:04
Speaker
And also subscribe if you haven't yet. you know Turn on the bell so that you don't miss the deep dives that are coming. And if there's if there's someone that you know that's at a similar crossroads that that needs to hear this, then please share this with them and let them know.
00:29:23
Speaker
That's how we're going to continue to build this community. So I'll see you in the next episode. Take care of yourself. And I'll say it again. Youth runs fast, but age knows the terrain.