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You’re in a job that pays well and has good benefits but you don’t want to be there. It’s not your favorite thing, or you may even actually hate the job, but it pays so well that you feel bad leaving it.

You’re scared of abandoning the stability it provides or fear that you would look foolish to your friends. Maybe you try to do something you’re passionate about on nights and weekends, except you come home from your job exhausted and spent. It feels like you’re spending all of the wrong kinds of energy and it’s taking everything from you.

Maybe you don’t have the time or energy after work to do what you really enjoy doing but it seems silly to leave a job so stable to do something else—especially if you’ve been at that job for years.

Maybe you have a lot of friends at the job or friends that know you work there who would wonder why you left: “What are you doing? We would all kill to be you! Why in the world would you leave?”

Golden Handcuffs. They come in many forms.


I want to give a special thanks to one of our Community members, Brent Galloway for designing the featured image on today’s podcast:

“Breaking free of the golden handcuffs can be one of the scariest decisions of your life. I know, because I left a secure paying job directly out of college to pursue my freelance career full-time. It was because of that leap I was forced to show up every day – to make a living for myself rather than depend on the benefits given by someone else.

I continue to learn and grow in the direction I desire everyday, and it’s all thanks to that initial risk I took to break free of my golden handcuffs.”Brent Galloway

Thanks, Brent!

Show Notes

Rethinking the Definition of Security and Work

  • 05:34 Sean: I received a message from someone saying, “I love getting paid each month and I’m so very aware of the people who would love to have this problem. I feel guilty sometimes for wanting things to change and not putting effort into preserving the status quo. For as long as I can remember, I’ve always wanted to grow and explore life under my own terms and I’ve never felt able to because I followed convention. I did what I thought was right. I did what I thought I was supposed to do. I followed the paths that I thought I had to follow but my future needs to be one of independence.

“I want to give myself and my family the freedom to choose—to choose how we spend our time, to choose how we live our lives, and to choose who we want to be.”

  • 06:31 Ben: One of the biggest problems is our definition of security. Emotionally, we feel like things are secure and we’re safe because we have the things we need. I like the use of the word convention there because a lot of times, we go into life allowing the conventions to define security, happiness, and financial stability for us. It puts all of those things into a narrow view.
  • 07:24 My wife, Rachel, and I have six kids now and things are tough financially but we’ve realized there are things that are way more important to us than the money piece. Even talking about Golden Handcuffs puts you in danger of defining success or security by the amount of money you’re bringing in or could be making with your passion, at the expense of talking about things like fulfillment, meaning, and purpose. You can’t put a dollar amount on those things.
  • 08:10 An example of this is that Rachel has been struggling emotionally because we don’t have the kind of financial security that she would be comfortable with. She’s focusing on her writing right now so she’s trying not to get other jobs. She’s not making any money at that but she’s worried that she should get a job and scale back on her writing, but just the other day, she got a message from someone who read an article Rachel wrote about a miscarriage we had about three years ago. This person was right in the middle of going through that.
  • 09:10 She shared with Rachel how encouraging and comforting her message was, so the kind of fulfillment you get from bringing that encouragement to someone’s life is worth far more than the security you feel from solid income or even making good money at your passion. Those values are often out of balance for us.
  • 09:45 Sean: The security thing is a big one. Maybe it’s also the way we define work. Some people might be in this kind of situation and not even know that’s what it is. I want to help people with recognizing if they’re in a Golden Handcuffs situation. Some people think you go to work and you come home exhausted and spent. You’re totally drained and you assume everyone else experiences that. You assume that’s what we’re supposed to expect from work, but it’s not. A lot of people experience that but it doesn’t mean that’s what we have to do, what we’re supposed to do, what we need to do, or that we’d be foolish for even trying to do something else.
  • 10:52 Ben: The misconception is that when you work hard, you should get to the end of the day feeling exhausted and drained. The reality is if you’re doing the kind of work you love and working hard at it, you’re going to get to the end of the day and you’re going to feel spent, but in a good way. You’re going to have fulfillment and a different kind of energy from doing the things you love. Even when you get to the end of the day and you just can’t work anymore, you’ll be ready to jump on the next day. A lot of people think it’s normal to feel exhausted, drained, and should dread going into work the following day.
  • 11:54 Sean: Because it’s a job—it’s work—but I have this crazy idea that we can also be fulfilled by our work.

Work doesn’t have to be something we spend a third of our lives hating so we can do the other things that make our lives bearable.

The Overlap Technique

  • 12:14 I think our work itself can be something that fulfills us. The Overlap Technique comes in when you’re trying to get to a place where the work you do is what fulfills you and is simultaneously what supports you, but getting to that point is difficult. Getting to that point means overlapping, which will either look like saving up money and transitioning out of a day job into something you enjoy doing, or it might mean making a slow switch—ramping down your hours at a day job and ramping up the hours you spend at something you’re passionate about. Golden Handcuffs tend to cloud things because you’re used to the security. You may have a lot of money but you’re just saving it.
  • 13:19 I was listening to an interview the other day about a guy who went to prison and was in there for five years. He got out and he basically missed being back in prison because he didn’t have as much to worry about. Obviously, he had stuff to worry about but it was a different set of problems. He had built up this image in his mind that once he got out, all of his problems would be solved. Everything was about getting out and when you’re out, you’re free but then all of these other problems arose that he wasn’t anticipating. He was used to the problems he had before. Maybe you’re used to the day job you hate but you at least know it will be there. You don’t want to think about the problem of lining up your next job. You’d rather have the problem of hating your job and coming home exhausted. It’s like the devil you know and the devil you don’t know.
  • 14:34 Ben: Many things in life are like that. I think about that with raising kids. Our kids are young right now and every day feels like a struggle to get them to do things and having to meet all of their many needs. Then, I talk to parents of teenagers and they talk about problems that are completely foreign to me. Here I am thinking, “Once we get out of this stage of life where they’re so needy, things will be easier,” but really, you’re just moving into a new set of problems. You could argue that you should get yourself to a place where you’re ok with the set of problems you have, or you could get to a place where you know there’s always going to be a set of problems to deal with.
  • 15:50 Sean: There’s a significant difference there, mentally. The problems you’re facing are problems that have arisen from a decision you’ve made or a position you’ve chosen to put yourself in. It’s a challenge that comes up because, with your freedom of choice, you’ve chosen to pursue something and that’s totally different from problems that are imposed on you and you can’t do anything about. When you’re building your own business, you’re going to have all kinds of problems but they’re problems that come from owning your own business! I own my own business so I want to wake up and face these problems and challenges head on because I’m motivated to do that. I have the energy from doing what I’m passionate about. There’s always going to be problems but you’re motivated to deal with the problems you choose to have.
  • 16:57 Ben: That’s why it’s fun to complain about my kids but at the same time, I love dealing with those problems because I chose to have kids and this kind of life style. The things I get to enjoy from having kids are well worth the struggles that come with it.
  • 18:02 Sean: You should start with the day job because you need to cover your expenses so you’re not in Scarcity Mindset. You don’t want to be in Scarcity Mindset because it will compromise your decision making abilities when you’re pursuing your passion. The day job should be your foundation. Most people are in Scarcity Mindset when they pursue their passion and that’s why you hear the stories about people doing their music or art and hating it. Well, that’s because they made choices that compromised the passion. You can’t afford to compromise the passion or you’re going to kill it right away. You’ve got to cover your bases first so you can afford to say no to the wrong things.
  • 18:56 Part of the Overlap Technique is getting a day job in place and the right kind of day job will charge you for your passion. You may not love the day job, it’s not your passion, but it’s covering your expenses and ideally, it’s not something you hate so when you come home, you’ll feel energized to pursue your passion on the side. You’ll feel charged and can’t wait to get home to pursue it.

The right kind of day job will act as a spring board, it will push you into your passion.

The wrong kind of day job will make you feel depleted.

  • 19:35 You’ll know it’s the wrong day job if you feel like the life was sucked out of you and you won’t have any energy. A lot of people have well paying jobs with benefits and they’re making plenty of money but part of the problem is that job isn’t an ideal day job as far as setting the foundation for the Overlap Technique goes. Most people in a Golden Handcuffs situation are making more than they need to cover their expenses or even twice what they need.
  • 20:26 Ben: Honestly, if I was in a job where I was making $120,000 a year but I only had a little bit of time leftover to hangout with my family and no time leftover to pursue my passion, it would still be difficult to walk away from. They may even give me 2-3 weeks of vacation every year and I could make enough money to do something really fun during that time.
  • 21:13 Sean: If you’re making twice what your expenses are, you’ve got to cut back because you’re not going to have the energy, time or recourses to even transition out of that. If you’ve allowed your lifestyle to creep up to what you’re making, you’ll have to scale back your lifestyle. You have to decide what you really want here:

Do you want to be trapped and well-paid or do you want freedom?

  • 21:50 Do you want the freedom to potentially make more than what you’re making now? If you’re able to make your business successful, it’s a real possibility to make a lot more than you’re making working for someone else. That doesn’t mean you won’t fail along the way because you will, but it also means accepting the risk and likelihood that you won’t be making as much as you are right now at the beginning. You have to decide for yourself what you want.

No Such Thing As Job Security

  • 22:18 With any job, even if it’s not a Golden Handcuffs job, there’s no such thing as job security. It doesn’t matter how secure your job feels or how invaluable they say you are, there is no such thing as job security. When you work for someone else, you are in their fortress. They’re protecting the fortress and making sure it stands but if that goes down—which happens all the time—all you have is the ability to find someone else’s fortress to take solace in. When you build your own fortress, you are now facing the risk head on because you’re at the top of the fortress. You’re seeing all of the dangers around you and the realities out there that you’re shielded from when you’re inside someone else’s fortress. You have to face those head on but if that fortress fails, you take with you the ability to build a new fortress.
  • 24:06 Ben: When you’re working for someone else, you don’t experience the same level of that risk but the risk is there nonetheless. Someone else is mitigating it and figuring it out through their own trial and error. When you experience that for yourself, the benefit you get is being able to see the decisions that caused that failure so that when you build again, you know how to work with those things. All of that said, you can’t foresee every scenario so I like to level the playing field there. I don’t want someone saying, “I don’t want to deal with that risk,” because one way or the other, you’re going to deal with it. You’re either going to experience it and run to someone else’s shelter, or you’re going to experience it and build resilience that allows you to keep rebuilding as you need to.
  • 25:43 Sean: In the chat room, Sarah says, “I know people who make really good money and lead a life that makes people envious, but hate themselves and hate getting up in the morning. I wouldn’t trade. I want to be happy when I get up from bed.” That’s true! The people who’s lives you see from the outside and observe to be awesome, you think they have it made. You think they’re happy but you don’t know that.
  • 26:40 Ben: Even if the money we make working for ourselves didn’t change and we couldn’t potentially make more money than at a regular job, the benefits we get from working for ourselves far outweighs the struggles we go through. Really, if we look back at our income statements and tax return, there’s minimal difference in the amount of money coming in vs. our expenses. The only difference that exists is who we’re working for. When we’re working for other people, not getting the kind of fulfillment we want out of life or the joy of being able to produce a lot of work, we’re still having the same kind of struggles. The struggles don’t really change.
  • 28:13 Sean: There’s nothing like working at your own thing. Employers want employees to be incentivized to do a good job and work hard but nothing compares to working hard on your own thing. You have this sole focus and you benefit completely when it does well. You’re able to pour yourself into that and it’s so fulfilling to be able to do that, but also to reap the rewards of it. When you put yourself in wholeheartedly, you benefit from it completely.
  • 29:03 Ben: When we’re working for someone else, it’s funny to think about the rewards we allow ourselves to think highly of. I was working for a bank and they had a system where if you performed well on your sales, you got bonuses. It felt like such a big deal at the time but when I think about the things I had to do in order to get those bonuses, the rewards were so small compared to the value I was bringing to the company.
  • 30:21 Sean: Working for someone else is like a flat rate and working for yourself is Value-Based Pricing. You get the full brunt—in a good way—of whatever value you create. You get an equal return on the value you put into the world.
  • 30:40 Ben: Often, you’ll see even more of a return. It’s amazing how much value comes back to you when you’re the one who’s facilitating that transaction.

Make A Plan of Escape

  • 30:54 Sean: Early last year, I was talking with a Community member in the chat room and he had a Golden Handcuffs situation where he was paid really well but felt paralyzed. He was scared to leave the security and stability of that situation. Everyone in the chatroom was encouraging him to quit his job and I remember him saying that he had $80,000 saved up—which goes a long way in Texas—and he still had no plan to quit.
  • 32:19 Ben: For my family of eight people with a relatively comfortable lifestyle, $80,000 would cover a year of our expenses and change. That’s a relatively short amount of time but still, it’s 12 months covered for a family of eight in Texas.
  • 32:56 Sean: I put that out there because it’s such a real thing to struggle with. If you don’t have an escape plan, then there is never going to be an end in sight. There is no number that will make it safe for you to quit your job. To plenty of us on the outside, having $80,000 saved up would be a no-brainer. That would last you a year or two, or even six months if you want to live insanely comfortably. You’ve got that much time to make this thing work, so why not try it? Worst case is to get another day job again. To us, it seems so obvious but it can be so paralyzing.
  • 33:45 I told him to get a number in place. Is there a number that would make you feel safe about going out on your own and trying something, and maybe failing at it? It was something he honestly hadn’t even considered and he hadn’t even spoken with his wife about it. We were telling him to get his wife on board because they really needed to be on the same page about it. This was last year that we walked him through the process of quitting his job. He’s actually in the chatroom right now and says:

“I’m happy my Golden Handcuffs are gone. They ended up being cheap, plastic handcuffs covered in a thin layer of gold.”

  • 35:00 Ben: Isn’t that really how it is? Aren’t all Golden Handcuffs simply plastic handcuffs covered in gold?
  • 35:13 Sean: It’s handcuffs no matter what, they just paint it with every raise—whatever shade or shimmer you want. He’ll be the first to tell you that he’s far from having all of his problems solved—he has a whole new set of problems. He now works for himself, which means he answers to himself. That sounds great and fun but it also means he’s fully responsible and has a lot of challenges.
  • 35:50 Ben: If you look at your situation and realize you have Golden Handcuffs, it’s important to talk to someone who’s working for themselves and ask them, “What are the things you didn’t know you would have to deal with and now have to deal with?” You won’t be able to account for every single thing but what scares some people, more than the answer to that question, is not knowing the answer to that question. If you can uncover some of that mystery, even if it still seems scary, at least you can deal with reality instead of dealing with the unknown.
  • 37:16 Sean: In the chat room, Scott says, “I hear what you’re saying but some of the handcuffs are actually made from precious metal. Plastic ones wouldn’t hold me for a second.” Guess what? They would if you think they’re gold. It doesn’t matter what the bars of your cell are made of. They could be made of bamboo but if you never try to kick them down because you think they’re made of wrought iron, then you’re trapped.
  • 37:47 Ben: The people who have the tenacity to test what the handcuffs are really made of are probably the people who are more likely to get out of them anyway. I can see what Scott is saying but I tend to agree more that it’s in our heads. The handcuffs, because we’re not fighting against them, could be made out of anything. The people who are fighting against them are the ones who are more likely to get out of the Golden Handcuffs without being encouraged to.
  • 38:33 Sean: Now, there’s people in the chat room talking about how interesting it is to hear how affordable life is in Texas, since we put out the real number of $80,000 and said it was plenty of money for an annual salary. Someone said, “Actually, it’s a little depressing,” but you’re missing the point. Say the number is $250,000 in Boston to meet living expensives, the number will fluctuate wherever you live. You’ll get paid more doing the same job somewhere else because of the cost of living. Don’t get caught up on the $80,000 figure we said, say whatever number you want. The point is you have to have a plan of escape because you could keep saving until you reach that number but you won’t leave unless you have an exit plan.

Get Your Spouse On Board

  • 39:47 I’ve been married five years now but we had to get on the same page even before we got married. It started when we were engaged. I was fortunate enough to have my own business before we were married and I was starting a second business while I was hiring out for my first business. I told my wife, Laci, “I’m about to put a lot of time and effort into getting traction to start up this business, are you sure you want to get married right now?” and she was on board. I don’t think she fully understood—neither of us could because we weren’t in that situation yet—but we went into it with a mindset of doing it together. I guess the fortunate part was that we were never in a scenario where we had a facade of security wrapped up in the consistency of a paycheck. We never had to transition out of that because it was always uncertain. We never knew where the next paycheck or web design client was coming from.
  • 41:45 Ben: Rachel and I both had regular jobs when we got married and even with jobs to where we could put money in savings, she had a budget outlined for us and she would get frustrated when we overspent in certain areas. We were doing music together, she was writing, and I was pursuing creative stuff on the side but our jobs were our main source of income and there was never a plan for us to get out of that. The idea was that we would keep our jobs until something worked out. What ended up happening to us because we didn’t have a plan was the bank upped the sales requirements—even though the market was going down and there were fewer customers—and upped the penalties for employees who didn’t meet the sales requirements, so I ended up being demoted until it didn’t make sense financially to stay there anymore compared to the other stuff I wanted to do.
  • 44:07 Rachel kept her job because she was still making enough money there and recently she was laid off from that job. We didn’t make a purposeful plan to overlap into working for ourselves and that has put us in a tough position. I want to encourage people to have those conversations and be realistic about the possibility of it happening to you sooner rather than later. What’s really helped us is that we continue to communicate. You might have to have that big, up-front conversation to get on the same page but beyond that, constantly communicating to make sure you’re still on the same page is vital for your sanity and health of your relationship.
  • 45:38 Sean: Laci is in the chat room right now and Sarah mentioned to her, “I’ve talked about you and Sean sitting on the ground saving up to afford a couch to other people when we were talking about waiting to afford things. Someone said, ‘His wife is patient!’ and I’m sure you are but in the end, I wish more people loved each other enough to be patient and believe in each other’s projects like that.” Getting your spouse on the same page is a big deal (Related: e097 Spouse Episode: The No-Debt Mentality). Both of you need to get on the same page and work together because you can’t do it alone. You can’t do it in isolation of your spouse, even if they have they’re own job and paycheck.
  • 45:25 Ben: Some people starting a life together by default think, “You’ve got to get furniture and all these things,” because that’s just what you do. Why wouldn’t we get a couch? You don’t think about what an impact each of those purchases and decisions you make when you’re merging lives has on your ability to pursue your passion. Maybe it’s because you don’t believe in yourself enough to make that distinction and say, “Sitting on a couch is less important than being able to invest in myself now so we can sit on a really nice couch five years from now.” Our furniture is in shambles right now and even if we could afford to replace all of our furniture, it wouldn’t make sense because the boys are just going to ruin it again anyway, but what’s the point of having nice things if you have no fulfillment in your life and you can’t be free to do the things you love to do or spend time with the people you love?
  • 48:31 Sean: Thrive vs. Survive. Do you enjoy that 1/3 of your life, or greater, that you’re spending at this job? You can get by when you go to your job and hate your life.

You can have a bunch of money and not really be happy, but is that thriving?

  • 48:51 Ben: The definition of thriving is important because to some people, thriving looks like having nice couches and having a nice car but it depends on where your values are. To me, thriving has come to mean I have enough time with the people I love and I’m able to invest in them emotionally and I have enough time to do the things that make me come alive vs. having nice things. Most people would look at the surface of my life and think, “It doesn’t look like they’re thriving,” but if you were to spend a weekend with us as a family, you’d see that despite our lack of nice things, we’re really thriving. How you define thriving is an important distinction to make.

Consequences of Golden Handcuffs

  • 50:35 Sean: You’re more risk adverse when you’re content with the problems you have, even though you hate that area of your life. If you don’t want to risk finding out that you have new problems and challenges, that’s a dangerous place to be. I’m not saying you should quit because I want you to be in a vulnerable position where you’re not able to pay your bills.
  • 51:09 Sooner than I would say to just quit if you’re making a ton of money and you hate your life, I would say to scale that back until you cover your expenses for a simple life while you make this transition. If it’s not that job, get another day job. Get a day job that doesn’t suck the life out of you. Get a job that will leave you feeling charged up and energized to do what you like to do. It’s dangerous to be risk adverse. We’re not talking about being foolish, we’re talking about taking calculated risks on doing something you love.
    • You don’t get to play this game of life again.
    • You don’t get another shot.
    • You’re spending your limited currency on what you decide to do.

Your life doesn’t start when you get home from work.

  • 52:14 It is your life! I would hate for people to be doing being stuff they hate because they think they have to—because they think that’s life, that’s work, and that’s a job.
  • 52:35 Ben: You can even find things in the home that are stealing your time away. Things that are more important to you because you think, “This is something we do and it has to be done.” An example of that for me is keeping a nice lawn. Those keeping-up-appearances things steal time away from the things I like to do and people I love. That time is significant to me so I would rather people think I don’t care about my lawn, because I don’t. I care so much more about being able to spend my time elsewhere. Ideally, I would love to have time to get to those things, the money to buy a new wardrobe, and to see a full bank account every month but if I’m not being real with myself about what’s more important to me, I can be in danger of feeling like I should be living that life—the life of working at something I don’t love or feeling strained at the time I have with the people I love.