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The Hard Truth About Working For Yourself After 50 - Do It Anyway
7 Plays2 days ago
The Hard Truth About Working For Yourself After 50 | Working For Yourself Series — Episode 1
You've been ghosted. Lowballed. Told you're "overqualified." The job market after 50 can feel like a door that keeps closing, and it's not your imagination. Age discrimination is real. But here's what nobody tells you: the smartest move might not be finding another boss. It might be becoming one.
In this premiere episode of the Working For Yourself series on the Ageism Survival Guide, we break down why working for yourself after 50 isn't just possible. The data shows it's more likely to succeed than starting at 25. A landmark MIT, Kellogg, and Northwestern study of 2.7 million business founders found that a 50-year-old founder is 2.8 times more likely to build a successful company than a 25-year-old. The average founder of America's fastest-growing startups? 45 years old. Not 25. Not 30. Forty-five.
So why aren't more experienced professionals making the leap? Three invisible walls hold them back: fear of starting over, identity tied to a corporate title, and the cultural myth that it's "too late." This episode dismantles all three with data, not hype.
You'll learn why your 30 years of judgment, your network, and your domain expertise are unfair advantages that no 28-year-old founder can replicate. You'll discover why service businesses like consulting, advising, fractional leadership, and coaching require zero capital to launch. And you'll hear the hard truths nobody else will tell you about carrying the full weight, unpredictable revenue, and the real isolation of self-employment.
We also cover the three pillars you need in place before you make the jump: financial runway (minimum 6 months, ideally 12), the four mindset shifts from employee thinking to owner thinking, and the single most important action step you can take this week, which is writing down the three problems you solve better than anyone else. Those three problems? That's where your business lives.
Plus: Ray Kroc started McDonald's at 52. Colonel Sanders franchised KFC at 62. The Kauffman Foundation found that 83.5% of entrepreneurs started by choice, not necessity. You're not too late. You're exactly on time.
Whether you've been pushed out, passed over, or you're just tired of playing a rigged game, this episode is your starting point. Watch now, do the homework, and start building something that belongs to you.
Next week in Episode 2: We break down the specific types of businesses that 50+ professionals can start, and which ones match your experience, your network, and your financial reality.
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Transcript
Is Self-Employment the Best Option?
00:00:00
Speaker
Hey, i I've got a question for you. Has it ever occurred to you that the person who'd make the best boss you've ever had is is you?
Challenges and Benefits of Working for Yourself
00:00:16
Speaker
You've been out there applying for jobs, tweaking your resume, updating your your LinkedIn headline. playing the game that you were told how how to play it and what have you got you've gotten ghosted you've gotten maybe some lowball offers you have interviewers where where they just sit there look at you and try to guess your age you've been looking for someone to hire you i i did in the past what if what if the answer isn't finding a boss it's becoming one
00:00:48
Speaker
Today is going to kick off a brand new series on this channel, Working for Yourself.
Resource Recommendations for Aspiring Entrepreneurs
00:00:55
Speaker
And I'm not going to sugarcoat this. It's the hardest thing that you'll ever consider doing.
00:01:01
Speaker
But I'm going to show you why it may also be the smartest. And before we dive in, if if you're watching this and you haven't been to the the new headquarters for for all things Ages and Survival Guide,
00:01:17
Speaker
please have a visit at ageismsurvivalguide.com. That's the new website. That's where all of the resources live, where the community can connect, and where you'll find tools that support every single thing that we talk about on this channel.
00:01:32
Speaker
You can become a member for free. You can become a paid member. You can have resources available at each level of membership. That's ageismsurvivalguide.com.
Invisible Barriers to Self-Employment
00:01:42
Speaker
Go check it out.
00:01:49
Speaker
So here is what we're going to cover today. First, three invisible walls that keep smart, experienced people like like you from even thinking about this route. Then we'll talk about why people like us actually win at this more often than the 25 year olds that people seem to worship, it the founders.
00:02:09
Speaker
And then the hard part, what you really need to have in place before you begin. Because i'm I'm not here to to sell you a dream. I'm here to give you a solid basis for decision making.
00:02:23
Speaker
and And that decision, it it starts with understanding why you you haven't considered this path before. Because it's not that you're not smart enough. It's not that you don't have the skills. It's it's because there are are invisible walls that that are holding you in place. And when you can't see something, you can't fight it.
00:02:46
Speaker
So let's illuminate those. The first wall is, it's fear. Not the dramatic kind, not the I'm gonna lose everything and and and you can't sleep at night, at mind racing. No, it's more the the quiet kind, actually, the dangerous kind, the kind that whispers into your ear and says, hey, I can't afford to fail, can I?
00:03:09
Speaker
but What it would if I do and I lose everything? I can't afford to start over. Here's the thing about fear at our age. It's not irrational. It's it's definitely not misdirected.
00:03:22
Speaker
It's just that you're afraid of the wrong thing. You should actually be afraid of spending the next 15 years working in a system that basically already decided that you're expired.
00:03:36
Speaker
Fear tells you, stay put, it's it's safer. But let me be honest with you, safer for whom? Safer for the employer who who can replace you with a cheaper version of you.
00:03:47
Speaker
Safer for the for the industry that's that's already kind of pricing you out. That's not safety. That's that's a holding pattern. and And holding patterns, they don't land. They just kind of circle around in the same position until they run out of fuel.
Overcoming Identity and Age Myths in Entrepreneurship
00:04:03
Speaker
Look, i was I was in the same position. I worked in a corporation and and I thought about maybe going out on my own, but I didn't because i had two kids looking forward to college. I had a mortgage.
00:04:13
Speaker
I had a future retirement that I wanted to save for. So I stayed in the corporation until the day that they restructured I was shown shown the door and then I didn't have a plan.
00:04:27
Speaker
I was suddenly having to massively accelerate my my own personal planning for my own business because I hadn't started it before. Out of fear.
00:04:40
Speaker
The financial fear, i hear you, it's it's real. I was there. you You have fewer earning years ahead. The math, it it somehow calculates differently when you're 50 than when you're 30. And I'm definitely not dismissing that. In fact, we're going to go more into the financial framework of all of this later on in the conversation.
00:05:01
Speaker
but But understand this. you're not You're not starting from zero. with your starting your own thing. you're're You're starting with 30 years of experience. You're not a 25 year old with without a network and zero credibility. You're a 50 year old who has a Rolodex.
00:05:19
Speaker
OK, ancient technology that took you 30 years to build. Fear, it says that you're going to lose everything. but But reality says you're going to own something.
00:05:35
Speaker
The second wall is identity. and And this one, this is kind of the silent killer. Because after 25 years or more, your your professional identity, it isn't just what you do it's kind of who you are.
00:05:51
Speaker
Director of operations, VP of sales, project manager, a senior accountant. That title titled It's not just on your business card. You allowed it probably like I did to get into your bones.
00:06:07
Speaker
And the leap from that to consultant, to entrepreneur, solopreneur, to I'm figuring it out. it It doesn't feel like a liberation at first. It actually feels a bit like a demotion, like stepping down, perhaps, instead of stepping out.
00:06:26
Speaker
But I want you to hear this. you're not abandoning your identity. You're you're actually taking it with you. The skills, the the judgment, the relationships, those don't disappear when you when you leave a company's regular paycheck.
00:06:45
Speaker
they They actually become your product. And and here's what the data shows. Older entrepreneurs don't just start random businesses.
00:06:56
Speaker
Look, you don't wake up and decide that you're going to start a sneaker company, right? We start businesses that are in our own domain, in our own industry, in areas that we spend decades learning about. And and now we apply all of that knowledge to our own business.
00:07:16
Speaker
and And then here's my irony alert. I love irony. You spent 30 years building your expertise that your employer now basically said was irrelevant. But when you when you work for yourself, that same expertise, it's it's your competitive advantage.
00:07:33
Speaker
The market doesn't value it. You know, that 35-year-old middle manager didn't care. But but your clients care. You care. And you can now leverage that experience.
00:07:47
Speaker
And the third wall? Huh. This is the biggest, the loudest, the one that the culture around you, around us, has been telling us since we were probably 45.
00:07:59
Speaker
Hey, the the ship has sailed. You you you missed that window. It's come on, man. It's too late to start something new. Right. You've heard all of those, I'm sure.
00:08:10
Speaker
This is not your fear. This is a ah cultural narrative. It's it's bullshit, frankly. And the data. It destroys that narrative.
00:08:22
Speaker
So a study from MIT, Kellogg and Northwestern analyzed 2.7 million business founders. 2.7 million. That's not some rinky dink little 200 people surveyed on LinkedIn. That's that's a huge survey.
00:08:38
Speaker
and And what did they find? This is great.
00:08:44
Speaker
A 50 year old founder. is 2.8 times more likely to build a successful company than a 25 year old founder.
00:08:57
Speaker
Not equally likely, not slightly more likely. 2.8 times. The average founder of the fastest growing businesses in America right now? 45 years old.
00:09:10
Speaker
You know, Ray Kroc was 52 when he started McDonald's. Colonel Sanders was 62 when he franchised KFC, and nobody talks about about those stories.
00:09:21
Speaker
But everyone knows about Zuckerberg and how he started Facebook in his dorm room. Nobody talks about Ray Kroc selling milk milkshake machines at 52 before changing over and and founding the whole McDonald's empire.
00:09:38
Speaker
Why does everybody know the the Zuckerberg story and and nobody knows the the Ray Kroc story? Unless you watched that movie a few years ago. Because the the culture sells us on this one narrative. that the The young founder, it's exciting. But honestly, the data, it tells a completely different story.
00:10:00
Speaker
Let me be honest with you. The people who are telling you that it's too late, They have a vested interest somehow in keeping you where you are.
00:10:12
Speaker
Employers, they want you compliant. Youth-obsessed culture, it wants to keep you invisible. And your your own fear wants you safe. None of these three are looking out for you.
00:10:27
Speaker
So if the walls are invisible, if the only thing keeping you from this path is a is a story that that that you've been told, then what's actually on the other side?
00:10:38
Speaker
What happens when when people like us open and walk through that door? Let me show you what the data actually says and and what it actually costs to move forward.
00:10:53
Speaker
The first advantage that you have is judgment. and And I don't mean just, you know, that you're wise in your years. I mean, something really specific. And I mean, pattern recognition.
00:11:06
Speaker
You have 30 years of solving problems, which means that that that's much more than any 28 year old founder has has ever even seen. You've watched strategies succeed and you've watched them fail. You've been in the room when decisions were being taken, wrong calls were taken, and you knew they were wrong because you'd seen that movie before.
00:11:26
Speaker
That's not just wisdom. that's That's a database that no startup founder can download over the weekend from ChatGPT or from Google. The researchers who did the MIT study, they specifically said the drivers of older founder success were experience, skill of running things, and insight about specific markets and technologies.
00:11:51
Speaker
It's not passion. It's not hustle. It's not disruption. It's insight. That's yours. That's what you have. You've been building that for 30 years, and nobody can fast track that one.
00:12:05
Speaker
Then there's the the second advantage that that you have, which is your your network. And this is honestly, this really unfair advantage for you because you can't replicate this again over a weekend. A 25 year old founder, they could be smart. They could even be brilliant, but they don't have the relationships that took three decades to build.
00:12:26
Speaker
they They don't have former colleagues who will pick up the phone for them. They don't have vendors that that trusted them after many contract cycles over the years.
00:12:37
Speaker
They also they they don't have a a client, a former client that that says, hey, you're doing this? I know your work. I trust you. I'm in. But that you have that.
00:12:50
Speaker
You have it. If you've been networking the way that we've discussed on this channel, building real relationships, reigniting them in some cases and not just collecting LinkedIn connections, you already have your first customers.
00:13:05
Speaker
you You just haven't called them by that name, by that label yet. And that matters because the number one way for new businesses to get their first clients It's not ads, it's not SEO, it's not a ah slick website.
00:13:21
Speaker
it's It's frankly, it's referrals from people who know you, who trust you, that you've been building that trust with over 30 years.
Financial and Mindset Preparations for Entrepreneurship
00:13:29
Speaker
It's now time to cash that in on your terms.
00:13:36
Speaker
The third advantage, and this is the one that makes the whole thing the whole thing doable. It's that you're not starting from scratch.
00:13:50
Speaker
Young founders, they they have to figure out everything, all of it. But you already know what do you know. The question isn't, what am I good at?
00:14:00
Speaker
The question for you is actually, how do I package what I know so that people are going to be willing to pay for it? So think about service businesses, consulting or advising, fractional leadership, coaching, specialized project work.
00:14:17
Speaker
All of these require actually zero capital. Zero. you don't You don't need investors. You don't need a ah product prototype. You don't need a warehouse, although you have a warehouse up here with all that knowledge.
00:14:31
Speaker
You just need a a phone, a laptop, and and your three decades of expertise that that nobody else is going to be able to replicate. Some of the most sustainable businesses out there, they don't they don't require money to start.
00:14:46
Speaker
What they do, though, require is is time. And you've actually already invested yours, learning what you know. And the fourth advantage that you that you have, this might be the most important one, and it's also the one that probably gets talked about the least.
00:15:05
Speaker
You're not trying to change the world. The 25-year-old founder, that person is chasing a unicorn. They want to disrupt an industry. They want to be on the cover of Forbes. they They're looking to build scale for growth for the exit after the IPO.
00:15:22
Speaker
and And nine out of ten of them, guess what? They fail because they were trying to hit a home run when a single would have sufficed to survive.
00:15:33
Speaker
But you, no, you're just changing your world. You're trying to build revenue have autonomy and have the dignity of of having your value be recognized by people, not not that middle manager back at the old company, as being relevant.
00:15:50
Speaker
And that, frankly, is a much more solvable problem and doable to climbing into a new business. Let's look at another angle of a of a study.
00:16:01
Speaker
So the Kauffman Foundation, they they found that 83 and a half percent of entrepreneurs, they started by choice, not necessity. These weren't desperate people who were forced into self-employment because because nobody would hire them. These were strategic people who who saw a better path for themselves and and and they ultimately took it.
00:16:23
Speaker
and And that could be that could be you. Not a refugee from ah from the job market, but but but rather ah a strategic decision maker who who saw the handwriting on your wall. Now you want to add to that handwriting.
00:16:36
Speaker
For me personally, this This epiphany came during COVID when the job market had completely evaporated. After a year of this, I learned, I researched, and and I investigated, and I took the decision to actually pivot into my own consulting business.
00:16:53
Speaker
It took the the trauma of my job loss to actually refocus my mind onto something better. Now, um before before you go and you hand in your your resignation, before you design your first logo, before you tell your spouse that you've got a brilliant plan, i need you to hear the the next part, because the same advantages that that make us more likely to succeed also carry with them a certain specific risk set. And and if you don't face those risks head on,
00:17:30
Speaker
those advantages you have don't matter. This isn't fluff now. This is not motivational posters. You need to have a whole bunch of stuff actually in place.
00:17:42
Speaker
So let's start with with pillar number one, the financial runway. And I'm alternately calling this the the math that nobody wants to do because people, they skip over this and then they wonder why after six months the whole thing collapses in on them.
00:17:58
Speaker
Here's the number. minimum, minimum six months of living expenses before you make that jump. That's not your startup capital.
00:18:09
Speaker
No, no, no, no. That's not the the kind of I'll figure it out kind of money. I'm talking about six months of mortgage and rent and groceries and and car payment and insurance and all of that. It's sitting in your account where you don't touch it.
00:18:24
Speaker
Even better is 12 months. Because the number one killer of of new businesses is not the lack of talent. it's It's not the lack of your hustle, your passion. It's actually running out of cash before the revenue really kicks in.
00:18:43
Speaker
And this is exactly why I talked about bridge work and in the stability series. You don't have to quit your day job on on day one. and In fact, I highly advise that you don't if if you have that option.
00:18:56
Speaker
the The smartest transition looks like this. So phase one, you you start your business while you still have a paycheck. Again, if you can, you validate the idea, you get your first clients, you prove the concept before you bet the house on Then you have phase two.
00:19:14
Speaker
Maybe you take bridge work if you need to. part-time contract temporary, this this reduces your financial pressure without making the full commitment on that business.
00:19:24
Speaker
it It builds up and maintains some runway for you while you develop your business idea. Phase three, you full-time self-employed only when your business can cover at least 75% of your living costs.
00:19:42
Speaker
Not 25%, not 55%, 75%. That last 25%, you're close enough. You're close enough and and and you can avert panic because if you do panic, it's going to make you make some bad decisions.
00:19:58
Speaker
If you can't cover six months of bills, you're you're not actually creating a business. You're you're creating an emergency. and And in an emergency situation,
00:20:11
Speaker
you panic and when you panic, you make bad decisions. It's panic that doesn't build businesses, but rather it destroys them.
00:20:23
Speaker
I'd like for you to actually, if you can write that down. Panic doesn't build companies, it destroys them. Because when you're three months in and the revenue isn't there yet and and the savings are shrinking, that voice in your head, it's going to start to say, hey, it's time to quit and go back.
00:20:44
Speaker
And if you don't have a runway, that voice might start to sound right. This isn't meant to scare you off. It's just meant to prepare you.
00:20:56
Speaker
The people who succeed at this aren't necessarily the the bravest. They're just the most prepared.
00:21:06
Speaker
And then there's pillar two. Mindset. and And I don't mean just a ah believe in yourself mindset. I mean four specific structural shifts in how you think because being an employee and an employer and an owner are two completely different ways of thinking.
00:21:24
Speaker
So there's shift number one from employee thinking to owner thinking. Look, employees, they they they wait to be told by the owner, by the boss, what to do. But owners, they know what needs doing. There's nobody that gives them a performance review. Nobody's going to be telling them or you if you're doing it right. Nobody's going to set your schedule for you or or or approve your vacation days based on what you prioritize.
00:21:51
Speaker
It's kind of terrifying, right? But at the same time, that's our freedom. Then there's the the second mindset shift that you have to have from identity in your title to identity in your value.
00:22:06
Speaker
You're not your job title. You are the the value that you deliver. The the title was was the label that someone else stuck on you. But your value, that's yours.
00:22:18
Speaker
So I want you to write this down if you can right now. Pause the video if you need to. okay I don't do brackets job title. I solve specific brackets problem for brackets people.
00:22:37
Speaker
Fill in those brackets. That is the the root of your business. That's your identity now. You're not the the former VP of operations, not the X director.
00:22:49
Speaker
No, now you solve X for I. And that makes your shift real and achievable. Then let's get to shift number three, mindset shift number three.
00:23:02
Speaker
From safety net to safety system. and A job is a single point of failure. One employer, one paycheck, one person who can decide on a Tuesday that you're done.
00:23:15
Speaker
That's not safety. That's 100% dependency. and And here's another irony alert. You think that your job is security, but you have only one client, your employer.
Practical Steps and Exploration for Aspiring Entrepreneurs
00:23:29
Speaker
I'd rather have five clients and no boss than one client who can fire me on a Tuesday. Look, a well-built business has multiple revenue streams, multiple clients, multiple paths, so that when one client leaves, the the whole business doesn't collapse.
00:23:51
Speaker
That's what I would call a safety system. And it's more resilient than any a single employer in my work history ever was.
00:24:02
Speaker
And the fourth mindset shift, the one that brings us full circle on this channel, it's from I'm too old to I'm exactly right.
00:24:13
Speaker
Not because I'm giving you a ah pep talk here, but because the data the data actually says it. A 50-year-old founder is 2.8 times more likely to succeed than a 25-year-old.
00:24:25
Speaker
That's not just some motivational pep talk. I'm talking i'm i'm talking probability. That's 2.7 million founders analyzed across the entire u s economy. you're You're not too old. You're exactly the right age where the data says the peak is going to be.
00:24:43
Speaker
And that means that the question isn't, am I too old? The real question is, am I too scared to go after what I want?
00:24:55
Speaker
And then let's talk about the the last pillar. I don't want you leaving this conversation in some feeling of of ambivalence. I want you to to to leave with something that you can actually do before the week is over.
00:25:10
Speaker
So before next week starts, I want you to do one thing. And and yes, i I always do these homework assignments. Write down the three problems that that you believe you can solve the best for other people.
00:25:23
Speaker
I'm not talking about your old job title or your old responsibilities. The problems, the the things that people came to you for, the things that when someone was stuck, they called you because they knew you could dig them out of their problem.
00:25:38
Speaker
Those three problems that you write down, those are probably the the seeds of your business. that That's where your revenue is going to live. It's not in a degree. It's not in a title. It's it's it's in the problems that you can solve for other people that they cannot solve.
00:25:56
Speaker
So write them down, sit with them, marinate in them, because next week in episode two of the series, we're going to start to to take these different problems and we're going to start turning them into something that people are willing to pay for.
00:26:13
Speaker
So let me pull this one together for today. There are three invisible walls. Fear, and it's pointing at the wrong thing. There's identity, what we think we've lost, but we need to leverage.
00:26:26
Speaker
And then there's the the the too late myth. And then we covered the 2.7 million founders who said exactly the opposite. You have four advantages. Judgment that took 30 years to build, networks that no startup founder can replicate, and knowledge that's already your product.
00:26:44
Speaker
And you also have realistic goals that make your success probable, not mythical. And then there are the three pillars that you need to have in place. You need your financial runway.
00:26:56
Speaker
Six months minimum, 12 months better. You have four mindset shifts to go through from employee to owner, from the the title to your value, from your safety net to your safety system, and from too old to exactly right. And then you have the concrete step of writing down the three problems you can solve.
00:27:19
Speaker
This isn't the easy path. It's your path. And I'm not going to pretend it's simple. Working for yourself, it means carrying the weight of all that W-2 that spreads across an entire organization. You become the the sales team, the operations team, the finance team, the ah HR department, all of it, all of it.
00:27:41
Speaker
I've been doing this for for six years, and it has been, frankly, frustrating. Exhausting and exhilarating.
00:27:53
Speaker
But here's what I know from doing this. You've been carrying the weight for other people's companies for decades. You've solved their problems. you've You've hit their targets. You've managed in their crises. and And they thanked you with a severance package, with a retirement package, and maybe a wish you well card.
00:28:16
Speaker
Now you carry that weight for something that belongs to you. and And every problem you solve, every client that you win, every dollar that you earn, it's yours.
00:28:28
Speaker
It's not theirs. It's time for for you to rise. Next week, we will start to get into different types of of businesses that you can start on your own.
00:28:40
Speaker
We'll examine different options and then you can compare those three problems that you've noted down with the different types of businesses and and how those businesses could be leveraged perhaps to solving the problems that you like to solve.
00:28:55
Speaker
If this episode really, really hit you, please like it, subscribe and and and share it with someone who possibly really needs to hear it because there are still a lot of people out there who are who are spending their time in front of job boards and and haven't even considered a path like this.
00:29:13
Speaker
You might be the the one who opens the door for someone else. And remember, ageismsurvivalguide.com. That's the website, the resources, the community, the tools, everything that I talk about on this channel, it's all there.
00:29:28
Speaker
Go check it out. And as i always say, youth runs fast, but age knows the terrain. See you next time.