Ep. #9: Boomers vs. Millennials

The “battle” between the Boomers vs. Millennials has much to teach us about creating wealth. When we get mired down in blame, we spend too much time finger-pointing and fighting, and we can’t see our opportunities. This episode will help us get out of frustration so we can start creating wealth.


Welcome to Rich & Thin™ Radio, the only podcast that helps you create wealth by shedding the weight that’s holding you back. Today’s episode is for every listener who’s been following the Boomers versus Millennials drama that’s been playing out in the news over the last couple weeks, and who is maybe feeling frustrated about that whole exchange. I’m Kelly Hollingsworth and I’m glad you’re here because the “Battle” between the Boomers and Millennials provides much fodder for discussion in terms of wealth-creation and entrepreneurship, so today I’d like to sort through some of that.

I’d like to start off by saying that this is not a political show. No sides are taken here, largely in part because I learned in the hedge fund world that nothing is good or bad. It’s all just opportunity. Hedge fund managers don’t care if the market goes up, or if it goes down. Either way is an opportunity, because they can position themselves to profit in either direction. This doesn’t mean they always pick the right direction, but it certainly gives them a lot of flexibility, and so rather than getting mired down in what should be happening versus what shouldn’t be happening, they just pay attention to what is happening and if they do this well, they make money.

The opportunity to profit from this kind of open-mindedness is available to all of us, but when we get sucked into things like the Boomer vs. Millennial battle, we can’t see it. Although some media sources question if the generational divide was invented by the media, what I saw in my LinkedIn feed last week would suggest not. My feed said that “as millennials face daunting student debt and the threat of job displacement due to automation, a majority say baby boomers are to blame” and cited a poll from Axios and Survey Monkey. “The survey results hint at a coming political battle, as baby boomers fight to preserve programs like Social Security and Medicare, all while millennials seek shelter from the coming shifts in the job market.” There were thousands of sarcastic comments left by angry responders.

This is the kind of thing that kills wealth. When we get mired down with what shouldn’t be happening, the Boomers shouldn’t have pillaged the plant and run up the debt, or the Millennials shouldn’t be watching so many video games on their phones and borrowing so much for student loans, when we’re focused on everything that shouldn’t have happened and who’s to blame, that’s when we lose sight of the opportunities that are right in front of us. We get ticked off at the culprits, and everything devolves to finger-pointing and name-calling, and we feel completely disempowered and angry.

None of this is a great platform for wealth-building, so let’s sort this out and try to look at it from a different perspective because there are some great lessons for wealth-building in all of this.

Employment versus Entrepreneurship

I’m not a baby boomer or a millennial–I am in the middle, a generation Xer, so like a classic middle child I would like to offer both groups is something that may help keep the peace. Both groups are frustrated about where the great jobs are going. The boomers are thinking they’re disappearing because they’re getting older and no one wants to hire them, and the millennials are thinking it’s because the boomers are living too long and working too long and sucking up all the resources in terms of social security and Medicare benefits.

The bottom line is that it doesn’t matter why the good jobs are disappearing, if they are in fact disappearing– a lot of people are still getting great jobs. But if they are disappearing, we have a choice to view that as a disaster or as a good thing. I’d like to invite you to do the latter, and here’s why:

We all have this idea that employment is safer. For example, it’s a lot easier to get a home loan if you have a regular paycheck coming in. But is employment really safer? When I had a job, I was very conscious that my financial future, at least in the short-term, was entirely in the hands of one decision-maker. If the owner of the business I worked for decided I was gone, I had nothing coming in until I went out and found something else. The day I quit my job and started working for myself, I began to diversify that risk across multiple streams of income. I was still doing the same kind of work, but I was doing it for two and then three and five and 10 and then 15 clients. Employment wasn’t safer at all. It just feels that way because we’re taught to seek shelter in the illusory certainty of a regular feeding schedule.

This brings me to my second point about employment. When you’re employed, your employer, the business that hired you, makes a certain amount of money off of your work and pays you a fraction of that. If you’re willing to forgo the illusory safety of employment and a regular feeding schedule, you make a lot more because there’s no longer a middleman a.k.a. the employer taking the Lion’s share of the money.

I could go on and on about the benefits of entrepreneurship versus employment. Safety, control over your own destiny, tax benefits, flexibility, but that isn’t’ what today’s show is about. The point is that the unhappy faction in both groups, boomers and millennials, are lamenting the job market and the increasing demands on employees and ignoring the fact that never before in the history of our planet has the world been so poised to support entrepreneurs and their efforts to achieve profits.

This is actually a huge benefit in my mind, because leaving employment typically means moving toward more money. I tripled my income the day I left my job, because the hedge fund I was working for had to hire me back. They couldn’t find someone to do what I did, so they were willing to pay three times my former salary. This is a very common experience for people who are willing to give up the illusory safety of employment. They start making real money and they enjoy a lot more flexibility.

Many of my clients come to me wanting to leave a job, but never have I had someone ask for help leaving a business and going back to a cubicle. It’s a one-way street. I haven’t had a job in a long time but from what I see in from when I read, jobs are getting worse and not better. In my mind this is a great thing, because it sharpens the contrast between employment and entrepreneurship. As the grass on the employment side of the fence gets increasingly dry and brown, it makes the green pasture on the entrepreneurial side look that much more attractive.

So for anyone in either group who is frustrated over finding a job, I’d like to offer that your frustration can end if you start viewing that as a blessing rather than a curse. I still think my lucky stars that the CEO at the last company that employed me and I couldn’t see eye to eye on anything, because if we could see eye to eye, I might still be employed and working for far less than the market value of my services.

The other thing that frustrates boomers and millennials alike is the rancor coming at them from the other side. Boomers view millennials in a certain disparaging way, and millennials view boomers in a certain disparaging way. We don’t need to get mired down in the details. I’m sure you’ve heard the complaints. The point I like to make here is that when we have disparaging thoughts about other people, we cannot see our opportunities. We feel really yucky, because thinking yucky thoughts about other people doesn’t do anything to them, it doesn’t affect them at all, it just ruins our day. But for the point of this show, I’d like to point out that extending a little love towards your “enemy” can make all the difference to your experience as an entrepreneur.

How do you do this? One way to begin is you can put yourself in their shoes. If boomers were born in the same time and place as the millennials, can they really say for a certainty that they would have done things differently? My guess is no. And I think it goes the other way too. If the millennials had been born in the same time and place as the boomers, they probably would have had the same experiences and done the same things as the boomers did. For the most part, people are a product of the time and place and culture that they come up in, and it is very difficult as an individual to see past all of that and come up with something different. It’s like that old saying about fish. Are they even aware that they are swimming in water? Are they aware that they are submerged? Probably not. It’s just their world and it seems completely normal to them.

Also notice how bad it feels when we think that someone else has an unjustified opinion about us. What comes up? We get defensive. We get angry. We want to get on our soapboxes and tell them why they’re wrong. This isn’t productive, and it’s also unprofitable. Fighting with someone else doesn’t generate revenues. All it does is keep us busy and make us feel horrible. So another way to get past our own bad feelings is to give people permission to think what they want to think about us. Of course, they already have this permission already. They can think whatever they want. But when we tell our brains that we’re granting them this permission, we stop feeling defensive and angry and frustrated, and we can get on with the business at hand.

Those are two ways to solve for anger and hostility. There are lots of others, but I’d just like to point out that hostility, anger, animosity are all just emotions, and they come from the thoughts we choose to think. Our thoughts can feel really true, but that doesn’t make them true. Often there something that is equally true or more true that we can grab on to that is much more productive and peaceful. And profitable. The other thing to remember is that our thoughts don’t have to be true to create productive emotions. I often hear it said that wealthy people are delusional, and that’s why they become wealthy. Think whatever you want to think as long as it is serving you and the emotions you want to feel, the actions you want to take, and results you want to create.

But however you do it, I can promise you that no matter what the environment, no matter how quickly and dramatically the landscape is shifting, there will be some people who make money and some people who make nothing and blame someone else.

Wealth comes to those who stop seeing the other as the enemy, because then they start feeling better and begin seeing the opportunity. It’s almost a cliché it’s so obvious, but the fact is that millennials know a lot about tech that many boomers don’t know and would find very helpful. Similarly, boomers know a lot of things that millennials would find helpful. Any skilled craftsman or expert in any field knows things that younger people would find helpful and want to learn.

There are cross-generational business opportunities available for anyone who wants to capture them, but we can’t see them when we are looking at the other as our enemy. Did you see the movie “Only the Brave? Yet? Jeff Bridges’ character apologizes for being a big jerk, and explains, “[w]e don’t see things as they are. We see them as we are.” In other words, we can’t see anything other than anger and frustration if that’s what we feel. We must change our lens and instead start looking for the people we want to serve. That’s where wealth is created.

Another important wealth-building concept we can glean from things like the Boomer versus Millennial battle is responsibility. We tend to have a notion that taking responsibility means that we are at fault. This is the view where we all look around when something goes wrong, and demand to know, “who’s responsible for this?” That’s about finger-pointing, and notice what happens when we do that.

If we look at the problems of the world and we point fingers at someone else, that puts someone else in control of the deterioration, and makes us feel out-of-control and powerless. What happens when we step into responsibility for a situation, whether we caused it or we didn’t cause it? The moment we step into responsibility, we feel empowered and confident. We feel like we can effect change, like there’s a reason to try, and this is a much better emotional place from which to try to accomplish something.

So what I’m offering here is that responsibility in the entrepreneurial sense is not about blame, it’s about opportunity. If you are the person who is able to respond to something, you are response-able, whether the problem is your fault or not. And the responsible people, the people who seek and find solutions, are those who are positioned to profit from them. Entrepreneurship isn’t complicated. It means solving problems in exchange for profits, and if any of us were living in a utopia right now, there wouldn’t be nearly as many opportunities. Seeing these opportunities is about changing your lens from blame to service. I see so many problems that can be solved through entrepreneurship right now I can’t even begin to count them.

Another thing we can glean from the boomer vs. millennial battle is this: A big reason so many of us aren’t seeing the opportunities is because our vision is clouded by a scarcity lens. The millennials are worried that the boomers have destroyed the planet and left them so much debt that there’s nothing left for their generation. The Boomers are worried that they worked their entire lives in reliance on a Social Security system that the Millennials are going to take away with their collective voting power.

We can’t possibly know whether anything that either generation is worried about will come to fruition. What we do know, however, is how thoughts like those make us feel. I went to bed the other night after reading a host of bitter comments from people on both sides and I felt frustrated and horrible. I was believing the comments. We have ruined the planet. There won’t be any Social Security. We’re in so much debt we’ll never dig our way out of it, and it’s all over and the economy is going under so why even try? I felt terrible and unmotivated to do anything.

The solution was to clean up my thinking. The problems are where the opportunities lie. I help people create wealth, so I need to focus on the most common problems that destroy wealth. These include overspending and overeating, which are really the same problem. Underearning, which is often about leaving employment and becoming an entrepreneur. Marketing better, which is about helping listeners distill the story of their marketing message so they don’t burn time, money, and effort on social media strategies that go nowhere. Another big problem we’ll cover in this show is investing better, because right now investing by the mainstream public is overwhelmingly skewed towards the continued and uncertain rise of the stock market. I say that the rise is uncertain because although the stock market in the long-term has always risen in the past, we can never know that that will continue to happen in perpetuity. We thought life expectancies would continue to increase generation by generation, but for the first time in the history of the world, our younger people are poised to live shorter lives than their parents. Things shift, and our investing strategies can’t take anything for granted. We can’t even count on a pension or government benefits, and entrepreneurship, and making business fun for people of all ages, is in my mind the cure for that problem. Those are the problems I’d like to solve.

What are the problems you’d like to solve? If you’re frustrated about the state of the world, asking yourself this question is the first step. Then assess your emotional state. If you’re looking outside of yourself at the shifting landscape and everyone else and the part they played in it and how it’s affecting you badly, if that’s bringing up anger and terror and anxiety because you’re worried you’re not going to have enough, you have some scarcity going on and it’s probably not serving you.

This is the second thing I had to remind myself about when I was feeling so frustrated after reading those comments: How easy it is to get stuck in scarcity, and what it does to us. When we think there’s not enough, we feel scared and deprived, and we take actions from a place of desperation, or we don’t take action at all, and we create a result of less rather than more.

So scarcity is something we do well to avoid. When I was worried about scarcity the other night, when I was feeling so frustrated about the state of the planet and Social Security and everything else, I found my way out by reminding myself of three things. The first is that no matter what happens, there will always be someone I can serve and a problem I can solve, and that means I will always have an income. The next thing that comforts me is that I know how to live on next-to-nothing, and I’m happy doing so. The state of our living situation is a circumstance. If it’s not luxurious, we don’t have to be unhappy. Some of the most moneyed people I know live like monks because they prefer simple, minimal surroundings. I lean that way myself. The last thing I tell myself to get out of scarcity is that resourcefulness is the only resource that matters. Whatever happens, I will figure it out.

This brings me to the final point I want to make for today in the Boomer vs. Millennial battle. Both groups are talking about the need for training, the need to be re-educated in something that’s marketable now. If you’re someone who’s seeking training and feeling frustrated that it isn’t there, what I’d like to offer you is that hunger for training is often more about credentials, confidence, and permission than it is about technical knowledge. The technical knowledge of most things doesn’t require any training. It requires learning, and that’s on you, not someone else. Learning can never be fed to you—and this is great news because you can feed yourself. If a credential is required, i.e. if you want to practice law, there’s no way around that but school, but that’s a special situation that’s pretty unique.

Mostly when we talk about training, sometimes we call it mentorship, what we’re talking about is confidence and permission, and those are things you give yourself. Our emotions come from our thoughts, not our mentors. For me, confidence comes from the same thoughts that help me get out of scarcity mindset: whatever it is, there’s someone I can serve, I don’t need very much, and no matter what happens, I’ll figure it out.

Permission comes from this idea: If not me, then who? May as well be me. and in my mind, it may as well be you, too. We all have too much to do to let the petty things get in our way, so let me know if I can help. kelly@richandthin.com. I look forward to connecting with you next week.

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