The MapleMoney Show » How to Make Money » Career

Turn Your Struggles Into Stepping Stones, with Karl Staib

Presented by Willful

Welcome to The MapleMoney Show, the podcast that helps Canadians improve their finances to create lasting financial freedom. I’m your host, Tom Drake, the founder of MapleMoney, where I’ve been writing about all things related to personal finance since 2009.

Do you find yourself in a constant struggle in an area of your life? It could be your job, your financial situation, or a difficulty in a personal relationship. If so, don’t miss this week’s episode because my guest is here to help.

Karl Staib is the founder of the Dig to Fly Method and author of Bring Gratitude. He trains people to turn their struggles into stepping stones. He has been featured by Forbes, NPR, and Zen Habits and has worked with great companies such as Philips Global, Southwest Research Institute, and Pioneer Nation.

There are times when we all struggle with feelings of frustration, anger, or disappointment. As Karl explains, these emotions are often signposts that something deeper is going on internally.

For example, you might feel angry about something your boss said to you at work. It’s easy to write it off as your boss being a jerk, but perhaps he or she has triggered a deeper hurt or struggle. This is why it’s important to take a step back and explore your feelings further. According to Karl, most people tend to overthink things, which makes self-reflection difficult.

Using his Dig To Fly method, Karl teaches people to tap into their gut instinct when struggling. Start by asking yourself: “How great is the struggle, on a scale of one to ten?” In the end, you’ll learn more about yourself, and you may even change your mindset. To get the full Dig To Fly method, you’ll have to listen to the episode. It’s one you don’t want to miss!

This episode of The MapleMoney Show is brought to you by Willful: Online Wills Made Easy. Willful’s intuitive online platform means you can create your legal will and Power of Attorney documents from the comfort of home in less than 20 minutes and for a fraction of the price of visiting a lawyer.

As an online entrepreneur, I’m always on the lookout for tools like Willful that can help me save time and money. Get started for free at Willful using promo code MAPLEMONEY to save 15%.

Episode Summary

  • So much of how we deal with life is about mindset
  • The value of using a gratitude journal
  • How to tap into your gut instinct
  • Karl walks us through the Dig to Fly questions
  • Questions to ask before quitting that job you hate
  • Why it’s so important to dig beneath the surface of our struggle
Read transcript

Do you find yourself in a constant struggle in an area of your life? It could be your job, your financial situation or a difficulty in a personal relationship? If so, keep listening, because my guest this week is here to help. Karl Staib is the founder of the Dig to Fly method and author of Bring Gratitude. He trains people to turn their struggles into stepping stones. He has been featured by Forbes, NPR and Zen Habits and has worked with great companies such as Philips Global, Southwest Research Institute and Pioneer Nation.

Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. Did you know that 57 percent of Canadian adults don’t have a will? Willful has made it more affordable, convenient and easy for Canadians to create a legal will and power of attorney documents online from the comfort of home. In less than 20 minutes, and for a fraction of the price of visiting a lawyer, you can gain peace of mind knowing you have a plan in place to protect your children, pets and loved ones in the event of an emergency. Get started for free at and use promo code Maple Money to save 15 percent. Now, let’s chat with Karl…

Tom: Hi, Karl. Welcome to the Maple Money Show.

Karl: Thank you for having me. I’m so excited to be here.

Tom: You have some interesting ideas I want to walk through. Things around career and work life balance is something I’ve struggled with in the past. One of the things on your site I want to just hop right into (which is a big open-ended thing) can you just explain what the dig to fly method is?

Karl: Yes, I started, Work Happy Now, back in 2008 because I was going to help people work happier. What I realized is a lot of people didn’t want to work happier. They just wanted a different career because companies were telling them they were lucky to have a job. This is back in the 2008 crash. In past 12 years, the world has shifted a lot too. More and more companies are hiring cultural transformation leaders. The people who have careers get a lot of surveys and are asked for feedback. This is happening more and more. We had to get through a lot of bumpy roads back in the 60s and 70s. You were in that career for life and you just kind of powered through it trying to get to retirement. Nowadays, we want freedom. We want autonomy to be able to do things we really care about. What I realized for myself is I got really sad and depressed when my father was passing. I went back to a gratitude journal because I realized how much I struggled with the whole thought process—what I was going through and how I was trying to deal with it. I’m an introvert. I prefer to write to process my thoughts and emotions. So instead of going to a therapist, which I had done in the past, I started keeping a gratitude journal. As I started doing that, it turned into a book. And through that, I realized there’s a process I’m using to help shift my mindset. What I really realized is life is 99 percent mindset. If you can find the right perspective on something… Just before we started recording, we talked about how one person goes all-in at work and loves it and another person, in the same exact role, hates it. Mindset is just so important and we don’t put as much emphasis and practice into it even as we do with our bodies. We know we have to exercise and make time for it. Very few of us make time to practice mental activities. Maybe we play chess, but a lot of times it isn’t getting a deeper understanding of ourselves. Maybe we see a therapist once a week, but what do we do to practice these things, to get more resilient, to be more resilient, to be happier? That’s where the dig to fly method all started. I put these sequence of questions together. We can go through the questions so people can actually try it themselves. What I realized is, it’s so important to create emotional space because we get caught up in our emotions and feelings saying, “Screw that!” We just want to throw in the white towel or tell somebody off. And it’s because we don’t have that structure of how to process those upset feelings. We’re told to breathe. We’re told to go for a walk. But then there’s no structure around anything after that. We can’t just call up our therapist so I created this sequence of questions that I’ve been using probably for the past couple of years now. And it’s funny… I’m a cynic so if I’m upset or struggling, the first question is, “On a scale of zero to 10, how difficult is this struggle?” And just before I answer it I think, “This isn’t going to work. I’m too upset right now.” And then lo and behold, it always calms me down and helps me find that switch in perspective. It’s just a thing where I realized other people could use this. I started using with my clients and I’ve been growing it ever since.

Tom: I’ve got to thought about that question. But first, I just wanted to clarify what exactly is a gratitude journal? What does someone do when they’re filling one of these out?

Karl: What you want to do with the gratitude journal is write down your “what” and your “why.” It’s a great way to start digging into your mindset because, when you see what you enjoy and why you enjoy it, that’s really key. Why helps infuse it into you. For example, I enjoy coffee. That’s great. And if you write a gratitude journal, you can say, “I enjoy my family. I’m grateful for a roof over my head. These are great. They get a very surface level response. You get that dopamine hit or you get that serotonin. Dopamine is to get up and go. And serotonin is that chemical release in the brain that helps you feel relaxed. And what’s so cool about gratitude is it can release both. It can release the get-up-and-go or the relax depending on how you use it. So, if you say, “I am so grateful for this cup of coffee,” it’s the serotonin because you’re saying, “This thing is in front of me and I’m with this thing.” You can also be grateful for the ability to take action. A lot of times I struggle to get out of bed, especially in the winter time but I’m grateful that I can put my feet down on the ground because there are a lot of people who can’t. I’m grateful that I can put my feet on the ground and get moving. Now we’re putting that switch on—that dopamine where it’s like you almost want to feel what it feels like to put your feet down. You’re starting to plant these little seeds of positive movement. But the dig to fly incorporates gratitude into it. So when you’re ready, I’ll kind of I’ll walk you through those questions.

Tom: Okay. That first question you mentioned—and I’ll get you to repeat it in a sec, but one of the things I immediately thought of is, on a one to ten range, I’m terrible at doing that. It’s hard for me to assign a number to a feeling or something like that. If you’re someone stubborn like me, how do you convince someone that this works so that I don’t just say one, five or 10 because there’s almost too many options in a range of one to 10?

Karl: This is what I like people to practice, tapping into their gut instinct. The idea is not to overthink it. You have a range of level of emotions, zero being the mildest thing you’ve ever experienced in your life. Usually when I work with people through their struggles the idea is, a fly lands on your hand. It annoys you. What (range) do you put that at? They might say that’s a “one.” Then you say, let’s say spending a year in a Nazi concentration camp. Where do you put that? They would probably say a “10.” The idea is, where does this feeling fall? Is it so overwhelming you can barely hang on or this doesn’t matter at all. Then you say, “Yeah, it feels pretty intense. It’s about a seven.” You just go with your gut. It’s not supposed to be fixed. You’re not supposed to stay at a seven. The idea with this process is, hopefully, after you’re done with it, after you go through the questions, you go from a seven to a five or a four because now you understand what’s going on inside yourself. Now you have some actions you can take so you don’t feel so overwhelmed.

Tom: I like that because there is room to maneuver on that range. I’ve got this the sleep app. I’m loving it in general, but when I wake up, the first thing it asks me is to rate one to five stars on how my sleep was. When you talked about overthinking it, I’m way overthinking it. I can spend a minute at least (which is way too much time) to consider it. It’s like, “Was this a three star sleep or a three and a half star?” I worry when there’s ranges, but I do like the idea. By having that you can treat things that are obviously different with that range instead of whether it was good or bad.

Karl: Yeah, exactly.

Tom: Can we go through these questions? I’ll just let you take over for a sec just so you can run through what they are and what they mean.

Karl: What I’ll do is ask the audience to plan a struggle in their head, something that you’re struggling with. It could be major or minor. It could be work or a relationship that you’re having—a disagreement that you had, trouble with a kid. Whatever it is, just think of a struggle you’re having. And as I ask these questions, just try to answer them as we go. The first question is, “On a scale of zero to 10, how great is the struggle? Zero being super mild, 10 being completely overwhelming.” And so as you think through it, you start to say, “Okay, my coworker has always put me down with these little snide remarks. It’s daily or every other day so it’s a seven. This is my career. It’s important.” Then you ask yourself, why? Why is this struggle bothering you? This is where you start digging down because you have to understand what’s going on. There’s still much more about yourself and so much about your perspective on this situation than it is this person. And it’s really up to you to figure out, “What’s going on inside myself?” Because if you’ve ever been had trouble with somebody in the past, if you’re in a good mood, they barely bother you. But if you’re in a bad mood, it’s like, “Oh, my God, this is insane. I can’t believe this person.” It depends on what’s going on inside you. If you say, “This person is bothering me, why?” You feel like they’re affecting your confidence. But why are they affecting your confidence? “Well, they make me feel stupid.” Why do they make you feel stupid? “Well, I made a mistake and they pointed it out.” Now you are starting to think about how you feel about yourself. What’s happening is this situation is a mirror onto how you’re feeling about yourself. Not how this person feels, but how you feel about yourself. And as you’re digging, you might say, “Why do I feel that they think I’m stupid? And why do I feel like I’m stupid?” It’s because sometimes I make mistakes. I made a mistake last week and got in some deep (bleep) with my boss. Now, we’re starting to see this pattern of it not being just this one thing. Now he or she is adding on top of this. Then you say, “What are your expectations of this person?” This is what is really key because we shouldn’t expect anybody to behave a certain way. They’re going to behave how they behave. Nine times out of 10, if you’re struggling with it, it’s because you expect the situation to be different. When you can be more accepting of this situation for what it is, then you’re less likely to let it just push you around and it gives you the freedom to choose other options. So, if you expect that person to be nicer, they’re not. What can you do about it? This is where the fourth question comes; what can you appreciate about this situation? There’s usually something small. Sometimes it’s hard. How can you appreciate somebody that puts you down and has these snide remarks? Well, it’s showing me that I need to do more work on myself because I’m letting them get to me. It’s showing me that they are struggling in life. Most of the time when people are acting out and lashing out at other people, it’s them having trouble inside themselves as well. It’s showing a mirror of who they are. Now you can learn about them as a person and know they’re having issues too and it’s not so much about me. That’s where the gratitude, the mental shift occurs. I’m grateful that I have a job. I’m also grateful that I have other great coworkers in this situation. There are a lot of good things in this situation, except, this part of it is tough for me. And then the fifth one is, what opportunities are here? And this is when you kind of dig down. You’re looking for these thoughts and emotions. I like to call them diamonds, because I think whenever we’re holding onto stuff, whenever we allow our emotions and thoughts to kind of push us around, it takes energy. If you’ve ever meditated, even if just for one minute, you find yourself drifting, “Oh, I’ve got to do this project and this project…” It takes energy. Your brain, I think, takes up 40 percent of the calories that your body intakes. And that’s huge. It’s a lot of resources. So when you expose these little bits of diamonds—these thoughts and bring them to light, what you realize is you’re holding on to these things, taking time and energy to think about them, when you can say, “You know, this coworker, what they think about me doesn’t matter because I know I do a good job.” Now you are starting to make that shift. And the opportunity here is, “I get to understand more about myself,” and I like to say external and internal. So internally you can say, “I understand more about myself. I’m starting to see some patterns.” A lot of times I call myself stupid inside my own head because I have a “stupid” complex. I don’t want to be perceived as stupid. A lot of times I’m afraid to speak up because I’ll be thought of as stupid and it’s taken me years to overcome this. A lot of it is from past experience as a kid, as an adult. I once had a boss tell me a monkey could do a better job than I was doing, which is terrible. And as you can see, it’s still sticks with me. But then there’s also external, right? Once you understand, internally, that you can have other perspectives on a person and realize you’re building them up when you really shouldn’t be doing that. You can find more confidence in yourself in other parts of life. These are just thoughts, though. I don’t have to believe what this person says about me is true. I can believe that I’m a good person. I can believe that I do my best at work. Maybe you’re not. Maybe you are half-assed in it and you’re saying, “Wait a second. I kind of am. Maybe they are giving me that little bit of nugget of knowing I need to step it up. I need to do a better job at work. I want to keep my job. I want to get a raise. Maybe I need to work a little harder or maybe I need a little work a little smarter. And then externally you can say, “Okay, maybe I want to take on this other project because I need to challenge myself. I’m coasting right now. That’s not what I want to do with my career.” And so now you have opportunities internally and externally. And that’s the stuff that helps give you a purpose. When you say, “I’m going to take on this this bigger project. I’m going to volunteer for it because I know it’s going to push me a little bit, but it’s also going to help build me up and put me on a path I want to be on versus this coasting path that I don’t want to be on.”

Tom: In your example, you’re much more empathetic to the other person than I probably would have been. I think I’d skip quite a few of those steps and just say, screw that guy. Then I’d kind of keep doing my own thing. But I like this idea of looking at all the different factors.

Karl: Yeah, but we forget about that. That’s what I’m hoping to do with this method, to take a pause . And when we stop, don’t let our monkey brains just run wild and attack this other person and throw poo at them. We should actually think they’re probably struggling too. Look at our current political climate. People say, “Oh, it’s terrible!” but it’s been like this for decades, for hundreds of decades. If anyone’s watched Hamilton recently, people had duels over political issues and shot at each other. It’s insane. This has been in America and other countries for many years. It’s tribal quality that’s kind of built into our DNA. But when we can step back and say, “Wait a second, I’m going a little overboard here and this is why…” then we can make choices based on that. Sometimes we just need to vent. Sometimes it’s you and another coworker who vent together. But is that helping you in the long run? What I’m hoping is, if you do the dig the fly method, you realize it’s not and that you need to take more positive steps and start making changes.

Tom: So with those positive steps, there’s obviously different ways you can improve your current situation. Like you said, you can take on a new project that might make things a little more interesting. It might help you move up the corporate ladder or whatever the case is. But then there’s also the other side of it where it’s just not going to work out no matter what job you’re in. What happens then? Is it just as simple as going to find another job or would you look more into finding something that’s perfect for you? What are your thoughts on if it’s time for a change?

Karl: There is definitely always time for some improvement at your current job and in finding something else. Because, if you just say, “This job sucks. I’m giving up. I’m going to just find another job,” that might take six to nine months. It might take a while. You’re miserable and making yourself more miserable every single day. That eats away at your lifespan. It eats away your happiness. The idea here is to say, “Okay, my boss is a complete train wreck and does not care anything at all about what I’m saying so I need to get out of here.” That’s fine. But why is your boss a complete train wreck? You might be able to find some hidden bits of ideas and opportunities there if you take the time to notice them and try to connect with your boss or try to connect with other people in your organization. You might have opportunities that you didn’t realize because you just put the blinders on and decided to go find a job someplace else. But when you go to that interview, you have less energy, less confidence because you’re not trying your best at your current job. And I think that’s the key. I’ve coasted before and made my life miserable because I said, “I just can’t wait to get out of here.” But I never really put in the effort because I had this job. I kept getting a paycheck every two weeks. I ended up staying at that job for a year and a half longer than I should have. My stress levels, my health, everything was a wreck because I stopped trying. I think if I would have tried the situation would have been better and I would have been more likely to find that other job because I had that confidence to do it.

Tom: I think I see that a lot, actually, where the people who are the least happy with their job are also the people that are putting in the least effort. It’s had to tell what comes first. It seems like a downward spiral where the more you are disengaged with your job, the more you’re starting to hate it. How do you break that cycle then? Is it by just going through these steps and finding out what you can do to change something?

Karl: I always say this is just a tool. A lot of people wonder if they should go to therapy, join a group, get a coach. But to be honest, all of those things are great. It just depends on your personality. My dad always used to say, just be yourself. What does that mean? How do you take action on that? That’s kind of where these questions came from. When my dad was passing, I was just writing the surface level of gratitude which helped. But it was just this a Band-Aid over this huge, gaping wound. I was grateful that I had a family and kept listing all these things I was grateful for but I never really got underneath it. I’ve had cancer. My wife had had skin cancer. And the thing with cancer is you can’t leave any tentacles because it will metastasize and keep going into other parts of the body so you’ve got to get underneath it. Well, these thoughts that are causing you to feel upset, angry, frustrated, these are all just signposts you can learn from. But you’ve got to dig underneath them to understand what’s going on. I used to get really upset in traffic. I used to get very angry. In coming back to question number three, expectations, I expected to be a point B faster. I would just scream and rage at other people. Then I just started thanking things because I was not going to keep doing this to myself. I’m not going to live this spiral of frustration and anger. It’s what my dad did a lot of times. I learned a lot of this from my dad. I just started thinking things. I started thanking the trees. I started thanking my eyeballs. I started thanking the clouds. I started thinking my car. And what I realized that in my car I had heat, AC—climate control. I have music that I can listen to. I’ve got podcasts. I can call someone. I’m sitting. I’m relaxed if I choose to be. This is a fantastic situation if I choose to look at it in that way. And so if you’re stuck in traffic, think about how bad it is on a scale of zero to 10. Maybe you’re at like a 9.9m right? If you just have a little bit of wiggle room, then you start asking yourself, why? You start going through the questions and it just calms you down. What I realized is no one really had a simple method. I say it’s simple, but it’s hard to do. A lot of times I’ve had some clients say the struggles of rating seven end up turning into an eight because they really understood that it was about themselves and the struggles that were a lot deeper than they expected, which happens. You see all the stories you’re telling yourself and you beat yourself up thinking, “Wow, I can’t believe I’ve been this evil to myself over the past 20 years.” I’ve been evil to myself, calling myself stupid, calling myself lazy. And when I stopped doing it, my confidence built back up. I felt happier. I felt lighter. I had more energy to tackle projects. I wasn’t afraid to tackle projects. In the past I didn’t have the confidence and would say things like, “That’s stupid, I can’t do that!” I would defeat myself before I started. And what I realized is I was beating myself up, holding myself back. And when you stop doing that and live freer—stop judging yourself so much… When you stop judging yourself, you stop judging other people. And then it’s just this whole domino effect of positivity that starts to take over your mindset.

Tom: I really like this idea because, again, just thinking back to some of the people I’ve seen over time in corporate life. The people who are being more positive are the ones who are going to get the fun projects. They’re going to get raises and promotions. You mentioned the domino effect, and literally, good things just start to come when you go with it and enjoy what you’re doing. I think this has been great. It’s going to change how I look at things a little because I don’t think I spend enough time on gratitude or looking back. I’ll hear from a lot of people about how I do all these things, how I’m successful here and there but I don’t really do a gratitude thing. I don’t celebrate wins. I just move on to the next thing. So, yeah, I’m really going to think about this because I think it’s something that can help me. I think for anyone in any kind of career, it’s obviously going to make their life happier but I think it’ll actually help them career success wise as well.

Karl: You bring up a really good point. In this process, when you dig in and start to take out these cancerous thoughts that are really beating your up, you start to create a habit around what’s going well. People who are listening right now, one of the things that can work really well is to keep a “what did you do well throughout the day” journal. I like to do this at the end of my workday. I wrote this really complex email that took me an hour and a half. I take a moment and pause to feel that and appreciate it. I never used to do this. I used to just go on to the next thing on my list. And what I realized was, even if it’s an email to a client, a sales email, or an email to your boss, you’re trying to lay everything out and really want to get it right, so take a moment. I like putting in my headset. I write it in my journal first, “Great job, Karl.” I try to compliment myself, “Great job on writing that email because it was well thought out and you did the best that you could.” Now that most of us are working from home, put on your favorite song and dance for a minute. Shake your butt around because when you start moving your body and really feeling that thing—that’s the stuff that sticks with you. It starts infusing into your bones. At the end of the night before you go to bed, if you’re planting the seeds of things you’ve done well, you’re going to sleep better and you’re going to remember those things because that’s what goes into your long-term memory. That is a little, awesome hack because now, instead of all the things you worried about, all the things you possibly did wrong (which is what we’re wired to do) you can think of three things you did well. Think about how well you did those things. Turn out the light and go to bed with those thoughts. You’re going to wake up with much more confidence the next day.

Tom: Another perfect example where I’m probably doing this wrong. At the end of my workday, I write down three things that I want to do the next day, which productivity-wise is great. It’s there and ready to go but it’s probably leaving me in a situation where by the time I go to sleep, I’m actually already thinking about what I’m going to do and not looking back at all. I think this has been great to inspire people to change the situations in their career. Can you let people know where they can find you online?

Karl: Yeah, If they go there, they can download the dig to fly method, printable. It’s basically all-in-one PDF where they can print it out and fill it out. I would suggest they fill it out once a day for 30 days. I usually do this on Sunday mornings. I think of what my biggest struggle is. I do it throughout the week but just mentally. If I just got an email back saying, “No, we don’t think your idea is that good. We don’t need you on you on my podcast…” Instead of allowing my anger to rise up, I’ll just start going through the questions really quick. I might rate it as a six, then see what opportunities might be there. The point is just taking the time to practice this. Even if you don’t do the method, take time to the pause and appreciate. Just practice that. Like we said, at the end of the day, take a moment to say, “Good job. I really worked hard on this. I’m proud of this.” That’s the stuff that’s going to help infuse that into you and you’re more likely to do better work the next day.

Tom: I love it. Thanks for being on the show.

Karl: Thanks so much.

Thank you, Karl, for giving us the tools we need to dig beneath the surface when we’re struggling with something at work or in life. You can find the show notes for this episode at Let me take a moment to thank you for listening to the Maple Money Show. I appreciate your support in helping us continue to grow. If you have the Apple podcast app on your phone, can you pull up the Maple Money Show and give it a quick rating? Even better, leave a review and let everyone know what you think of the show. Thanks, as always, for listening. I look forward to seeing you back here next week.

One person goes all in at work and loves it, and another person, same exact role, hates it. Mindset is so important, and we don’t put as much emphasis and practice into it. - Karl Staib Click to Tweet