In this episode of Executive Connect, Melissa Aarskaug sits down with Gregory Russell Benedikt, a former finance professional, coach, and TEDx speaker, to talk about what happens when external success stops feeling meaningful. Greg shares the quarter-life crisis that changed everything, why he walked away from private equity, what 100 days of rejection taught him about courage, and how bold action creates the momentum most people are waiting for.

This episode is for high achievers who look successful on paper but feel stuck, burned out, or disconnected from the life they actually want. If you have been telling yourself, “I’ll be happy when,” this conversation will challenge that story in the best way.

Press play before your next promotion talks you out of your actual life.

Chapters:
(0:01) Why empty success feels hollow
(1:17) The moment everything changed
(3:23) Letting go of old identity
(5:49) Why society rewards achievement
(12:17) What rejection really teaches
(22:10) Why bold action works
(27:20) How to start chasing meaning
(39:29) Lightning round on fear and success
(41:04) Final advice and where to connect

Gregory

(0:00) I get it. (0:00) I get what it’s like to be overworked, underslept, tired, burnt out. (0:05) Like you’re really trying your best to show up and achieve all these things that you actually genuinely think will make you happy.

(0:10) And you get to go on the journey to find out whether those things will make you happy, whether that’s true or not. (0:15) But give yourself some grace, create some time to slow down and have that pause like Melissa and I are talking about. (0:20) In that pause, in that curiosity around, is this really what I want to do with my life?

(0:25) Is this what I want to do for the next 10 years, next 15 years? (0:27) That’s where a lot of the magic and your answers will come from. (0:30) So start small, get curious about this.

Melissa

(0:32) What’s scarier, failing at your biggest dream or never trying at all? (0:38) Most of us play it safe, check all the boxes and end up wondering, is this it? (0:44) Today’s guest, Gregory Russell Benedict, refuses to live that story.

(0:49) He walked away from finance, built a nonprofit with a stranger off the internet and now helps people trade their empty success for a life worth telling. (1:00) Buckle up if you’re ready to take and talk about bold moves, massive action and why the universe rewards those who dare. (1:08) Welcome Greg.

Gregory

(1:10) So happy to be here, Melissa. (1:12) Great to see you again.

Melissa

(1:13) Great to see you. (1:14) Now let’s start from the very beginning. (1:17) You had what a lot of people would call a dream job in private equity, but instead of staying in your lane, you completely pivoted.

(1:30) What was the breaking point for you?

Gregory

(1:32) Oh, I love that question. (1:33) And when you were saying you had what people would call, I thought you were going with existential life crisis, because that’s what started this entire journey I’ve been on. (1:43) So back in November of 2019, I was in Tokyo, Japan, and I had a full blown quarter life crisis rock bottom moment where I was listening to a podcast and I learned that most people at the end of their life, not only do most of us have regrets, but that we all have the same top five regrets.

(2:03) They’re called the top five regrets of the dying. (2:05) And this woman named Bronnie Ware, she was a palliative care nurse. (2:09) She sat with over 500 of her patients on their deathbed and asked them, hey, do you have any regrets in life?

(2:16) You’ve had a great life, but is there anything you would have done differently? (2:18) And she found out that the number one regret people have at the end of their life is, I wish I would have had the courage to live a life true to myself, not the life others expect of me. (2:28) And when I heard that, it slapped me in the face.

(2:32) I was working in finance at the time. (2:34) I was still party Greg. (2:36) I was still drinking because my friends wanted me to.

(2:38) And my whole life just felt unaligned. (2:42) And because of that, I didn’t feel very alive. (2:45) I felt like I was living someone else’s life, wearing a mask, hiding how I truly felt about everything.

(2:50) So it was that moment that was the rock bottom moment that made me decide to go all of 2020 sober, a very interesting year to not drink and to quit my job in finance. (3:02) So later that year in June, after saving enough money that I could live comfortably for a while, I quit my job in finance and that was the big moment for me.

Melissa

(3:11) Yeah. (3:12) I love that because huge shift in identity. (3:16) I’ve been there.

(3:17) I’ve been that ride. (3:18) I know what that feels like, but talk to me a little bit about the identity piece of that. (3:23) What identity did you have to let go to make this leap living one life and pivoting to a completely new life that you hadn’t had really a lot of experience living?

(3:34) Ready to lead smarter and invest wiser on the Executive Connect podcast. (3:40) We unpack executive strategies for wealth and influence. (3:45) Hit the subscribe button now.

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Gregory

(3:49) I had to let go of several identities at once, which is never easy. (3:53) One of them was the identity of being the young, successful man working in finance. (3:57) My parents were proud of me.

(3:59) My parents’ friends were proud of me. (4:00) I’m sure my college professors were proud that I did what I set out to do. (4:05) I had to let go of the identity of being the risk averse, calculated, analytical, logical person who also worked in finance.

(4:14) And for the first time in my life, I leaned into a new identity, which was I am now someone who takes bold action, but more than that, someone who trusts the unknown and leans into the unknown. (4:27) That has been one of the greatest lessons I’ve learned throughout my life, both personally and then working with all of my clients, is that that unknown is so scary to step into. (4:38) We love certainty as humans.

(4:40) We crave it. (4:41) But every time you’re willing to put yourself into the unknown because you know that there’s something greater for you, you know, deep down that you’re capable of more. (4:48) That’s when the magic happens, because in the unknown is everything, every potential, every possibility, every new opportunity.

(4:56) But again, it’s super scary because we are our identity. (5:00) The identity is very important. (5:01) It’s our construct.

(5:02) It’s our ego. (5:03) But to shift into what I call living a story worth telling and to go after your biggest dreams, you know, I’m big on going after dreams. (5:12) We often have to let go of our old identity, define a new identity, and then figure out how can we take small steps to actually embody and step into that identity.

Melissa

(5:21) Yeah, I love that. (5:22) It’s so true. (5:23) And tell me this, I personally feel like society awards, receives awards for those based on what they’re achieving out in the world, whether it’s a job or a raise or a title or whatever it is in the world.

(5:36) But it doesn’t really reward when we’re aligned with who we are and where we’re trying to go based on our skill set. (5:45) So why does society reward achievement more than alignment?

Gregory

(5:49) Oh, I love that question. (5:51) I think there’s a couple reasons. (5:53) One is that it’s just easy.

(5:55) It’s much easier to point at someone’s achievements and success and accomplishments and say, wow, you did all these things. (6:02) They look super sexy and shiny on the outside. (6:05) Good for you.

(6:06) So I think it’s simpler. (6:08) It’s observable. (6:09) It’s very hard to look at someone and know what are their relationships like?

(6:16) How are they living in alignment with their values? (6:18) Are they showing up in integrity with what they believe versus like, oh, they make this amount of money? (6:23) Very easily measurable.

(6:24) And then also kind of on the simplicity standpoint, society rewards people for doing what is known and expected and easily explainable. (6:34) So if you’re a doctor, super easy to answer that question when someone asks you what you do for work. (6:39) If you’re a finance, my journey of trying to shift from finance into whatever was next, which for me ended up being leadership and executive coaching.

(6:50) It was messy because for the longest time, that was the hardest question to answer. (6:54) Someone would ask me, hey, what do you do? (6:56) And I would be so scared to say that, oh, I’m a coach now.

(6:59) So for about a year and a half, I was like, well, I used to work in finance and X, Y, Z. (7:04) But now I do this. (7:06) And so back to your question of why does society reward achievements and accomplishments?

(7:11) I think it’s an easily observable metric. (7:15) And it’s. (7:17) It’s that’s the hard part is that you can get all of the praise from the outside, you can be successful on paper, as I call it, but your soul can be empty.

(7:26) And that is what I love helping people with, because I only work with people who are successful now. (7:31) That was a whole bridge I had to cross. (7:33) But I work with highly successful corporate professionals who feel trapped and are asking themselves, is this it?

(7:40) Because they’ve gotten the job title, they’ve made the money, they have the cars, they have the house. (7:45) And society is telling them, wow, you’ve made it. (7:48) But on the inside, they feel empty.

Melissa

(7:51) And I love this. (7:52) I mean, we can spend hours talking about this subject. (7:55) I just wrote a recent article mainly because of some feedback I received for taking a new job last year.

(8:04) And I called it the reinvention myth. (8:07) Why starting over is actually a leadership skill versus a personal crisis or they couldn’t cut it or they couldn’t hack it or whatever we hear that’s out there. (8:20) And so I love that you are working in that space, because I think the interesting part about that is some of the most successful people in the last year that I would I would look up to or would have in my younger years are begging to get out of their situation.

(8:38) And they would trade their current, every accolade, all their credentials, all the money. (8:43) And exactly like you said, for more happiness, for more peace, for loving friendships, for a loving relationship, for more time with their kid. (8:51) So why do people postpone meeting their meeting of their life for security?

(8:58) Why are they postponing what they want to do with their life or where they want to go for security in their current job?

Gregory

(9:05) I want to answer that. (9:06) But first, I just want to piggyback off of what you said about reinvention and making that pivot. (9:11) And I think actually I can tie these two together because pivoting is difficult.

(9:16) If you have built yourself up, you have this reputation, you’re the maverick in this industry, but you want to go do something different. (9:23) That’s scary. (9:24) And you have to set out on what might feel like a new journey, but it’s never a new journey.

(9:29) You’re never starting over, like you said, because you’ve built up who you are as a person and you’ve had all these experiences. (9:36) And it’s not like you reset your personality or your skill set as you go into something else. (9:40) So I love what you’re saying about starting over and reinvention.

(9:44) It’s not going back to square one. (9:46) It’s consciously deciding to go to the next level or the next industry on purpose. (9:51) And to make that pivot, most people want to do that without lighting their entire life on fire and without losing their ability to provide for their family.

(10:01) And that is something that I’ve had to learn the hard way is when I work with clients and especially in my marketing and talking to prospective clients, like making that abundantly clear. (10:10) We’re not saying that you’re going to go quit your job tomorrow and move to the Himalayas to meditate in a cave. (10:15) You have these real things that you need to handle, take care of.

(10:19) You have a family, you have a mortgage, all the things. (10:22) And so that ties into why people put off meaning and fulfillment, which I truly think that what people think they want is happiness. (10:31) But what we really want is meaning and fulfillment and alignment.

(10:35) And it’s funny and ironic because to get those things, you can’t obtain them directly, but they come to you as a byproduct of going after a dream, going after that meaning in your life. (10:48) People put it off because it’s hard. (10:50) It is so much easier to just keep telling yourself the lie that I’ll be happy when.

(10:55) I’ll be happy when I get promoted. (10:57) I’ll be happy when this really difficult boss I work for no longer, I have to report to them. (11:02) I’ll be happy when I get more money because then I can solve these problems.

(11:07) And people have to go through it to a certain extent on their own. (11:12) You have to get to the point where you’ve made the money, you’ve achieved all the goals that you said would make you happy and you’re still not. (11:18) That’s when you start to realize that meaning is worth pursuing.

(11:22) And often a lot of my clients are older. (11:24) Like a lot of my clients come to me either in the midlife crisis or kind of post midlife crisis as they’ve realized there’s more to life than money and achievements. (11:36) But it is really hard because the external world will reward you for doing the things that on paper make you look successful.

(11:44) But something I say all the time is that all the success in the world, if it’s not aligned, it feels hollow.

Melissa

(11:51) Yeah. (11:51) And you’re burnt out quicker, right? (11:54) You burn out doing things you hate doing faster than if when you’re doing things you love.

(11:59) It’s amazing to me. (12:01) You know, when I sleep three hours, but I’m doing what I love, I have a ton of energy. (12:07) When I’ve slept eight hours and I’m doing something I hate, I’m ready for bed.

(12:11) And the more we do what we love, the more we have boundless amounts of energy to power through the day. (12:17) I want to talk about this 100 day challenge, 100 day rejection challenge. (12:22) You took on something most people would run from, 100 day rejection challenge.

(12:31) What did you face or maybe the better question, what did facing rejection over and over actually teach you?

Gregory

(12:39) So many good things. (12:41) And I’ll just set the stage for this story a little bit, which is, there’s a brilliant book called Rejection Proof by Jia Jiang. (12:50) And he went on this journey in like 2013 and he wanted to overcome his fear of rejection because he was trying to start his own company and kept getting rejected by VCs.

(13:01) So I read this book and I read this book maybe in 2021 and I read the book and I’m so excited and I’m so fired up and inspired and on fire. (13:11) And then I did what most people do, which is I put the book back on the shelf and I moved on to the next book on my reading list because I had like some goal to read a hundred books or whatever. (13:20) And then just a couple of years ago, I reread Rejection Proof and I had all the same feelings.

(13:27) I had these feelings of motivation, inspiration, excitement. (13:30) And I was like, wait, wait a minute. (13:31) I’ve been here before.

(13:33) I have about 10 seconds to go act on this. (13:36) Otherwise, I’m just going to put the book back on the shelf and it’s going to be the same story. (13:39) And so I decided to personally embark on 100 days of rejection and I live in San Diego.

(13:46) So I made it, I wanted to make it my, a little twist. (13:49) So I said, I’m going to do 100 days of taking bold action and trying to get rejected by strangers. (13:54) And what I learned from it was that how we build confidence is putting ourselves in uncomfortable, hilariously outrageous situations over and over and over again and having everything turn out fine.

(14:09) And what I mean by that is that I learned that strangers are not as scary as the internet will make them seem. (14:15) People are awesome and kind. (14:18) And every time I asked someone for something outrageous, even if they said no, we had a laugh.

(14:23) We created this little moment together. (14:24) We created this story that I’m sure they went home and told their significant other, like, you won’t believe what this weird guy with a mustache asked me today. (14:33) And to make a very long story short, on day number four of my 100 days, I knocked on a stranger’s and asked if I could cannonball in his swimming pool.

(14:42) And he said, yes. (14:43) And we filmed a short video of me doing this. (14:46) I posted it on Instagram.

(14:48) It went viral. (14:49) And throughout the next 96 days, I had this whole cohort of people online rooting for me, cheering me on, telling me what I should do next for my outrageous asks. (14:59) And eventually, I didn’t know it at the time, but eventually that journey of taking bold action, talking to strangers, it led me to meet the love of my life.

(15:09) And I actually have given a TEDx talk about it that also went viral. (15:13) So this idea of taking bold action and that the universe actually rewards bold action, it really resonates with people.

Melissa

(15:22) Yeah, I love these stories. (15:24) And funny enough, that’s how we met. (15:26) I just happened to stumble upon you on the internet and we’ve become friends.

(15:31) So here we are filming a podcast. (15:34) Talk to me a little bit about how rejection changed your nervous system. (15:41) Money Ripples is on a mission to help professionals just like you get their money working harder for you.

(15:48) Their clients free up an average of $35,000 their very first year without having to work extra hours to show you how they’ve put together a powerful training called Cashflow Secrets. (16:00) And the listeners of the Executive Connect podcast can get it completely free. (16:05) Just visit moneyripples.com forward slash secrets and enter the promo code EXEC.

Gregory

(16:12) It is a work in progress. (16:14) I will say that. (16:15) I still get nervous.

(16:17) I still get scared. (16:18) I still get the sweaty palms and the sweaty pits. (16:22) And that has been part of my journey is to show that that’s OK.

(16:27) Like that is to be expected when you are getting out of your comfort zone. (16:31) And in this talk, the thesis is that fortune favors the bold, which is this quote I always loved growing up, that it’s not just a quote, but it’s a formula for how the universe works. (16:42) And that if you’re able to increase the boldness in your life, which we do have control over, you can inadvertently increase your fortune or what happens to you in life, which typically we don’t have that much control over.

(16:56) So by putting yourself in those uncomfortable situations that make your heart pound and make you feel alive, you can actually influence the outcome of your life. (17:08) And that’s the whole thesis and how it’s impacted my nervous system and why I recommend this to everyone is going back to the confidence piece. (17:16) If you know that you have asked a stranger for something outrageous or you’ve been in this scenario over here when you’re at work and you’re in a meeting and someone says something that bothers you a little bit, you’re not going to respond as much.

(17:28) So seeking, seeking rejection, seeking intentional rejection, voluntary discomfort, as I call it, it expands your frame and your capacity to handle things. (17:40) In therapy world, this is called your window of tolerance. (17:45) So ways to increase your window of tolerance are sleeping a lot, like sleeping well.

(17:49) If you’re in a good mood, you can handle a lot. (17:51) But I also think that seeking rejection and putting yourself on purpose in uncomfortable situations expands your ability to handle the discomfort when it’s not voluntary. (18:04) So when something bad happens that you don’t have control over or you didn’t put yourself in that situation.

Melissa

(18:09) I have so many questions to ask from that, but I’m going to, I’m going to pause because I’m going to ask you another question. (18:15) So a two part question. (18:17) So what happened to fear for you over time, the more you did this, and what did you realize about embarrassment during this hundred days?

(18:29) Because I have to imagine there was probably some really awkward conversations, like you said, alluded to. (18:37) So fear and embarrassment, how did over time, what changed for you?

Gregory

(18:42) Yeah. (18:42) Fear, I learned is probably the number one thing that keeps people stuck. (18:47) Fear of the unknown, fear of what people will think, fear of what might happen, fear of embarrassment, fear that we will look silly, that we will fail in public.

(18:56) And I learned that fear is a good thing. (18:59) I reframed my relationship with fear. (19:02) I now see fear as a compass.

(19:04) If I’m scared of something, instead of running away from it, it probably means that I should run toward it because we feel fearful. (19:11) And again, let me caveat this with this is more of the intellectual and emotional fear. (19:17) If you’re feeling physical fear for your well-being because you’re in a dangerous area like that is completely different.

(19:23) So please don’t run toward that. (19:25) This is all of the fear that comes from what I mentioned, the self-doubt, the imposter syndrome, what will people think of me? (19:33) The more we can lean into that, the more we become who we’re meant to become.

(19:38) Because the reason we are fearful is because it matters to us. (19:43) If you think back to when you went to take your driver’s license at age 16 or so, you’re probably really terrified to do that because that was so important to you at that time. (19:54) And now if I had to go take a test to get my license renewed, I wouldn’t be worried at all because that isn’t the most important thing in your life.

(20:02) When you’re 16, that’s one of the most important things. (20:05) So fear comes because the thing is important to you. (20:09) And if you’re able to push through that fear, everything you want is on the other side of it.

(20:14) So long way of saying, I see fear as an indication of what I should run toward. (20:21) Embarrassment is the best. (20:25) The more embarrassment that you can take on in the present moment, your future self will thank you for it.

(20:32) Because I have this theory that if you aren’t feeling cringe about your past, you probably weren’t growing enough. (20:41) If you think of yourself five years ago and you’re like, oh yeah, I was doing everything right. (20:46) Like I feel comfortable with what I was up to.

(20:49) That might not be great because I look at myself five years ago and I thank myself for doing all of the cringey stuff like quitting my job, saying I was a coach, starting a podcast, like trying all of these new things because it means that you’re willing to grow. (21:03) And I see embarrassment as an indicator that you’re going for it. (21:08) Embarrassment usually comes because you’re doing something that is uncomfortable.

(21:11) It’s unknown. (21:12) There’s other people watching. (21:13) There’s other people who might be thinking about what you’re doing and how crazy it might be.

(21:17) And again, it’s just building your capacity to live a life true to yourself and not let other people’s thoughts and judgments get in the way.

Melissa

(21:26) It’s so true. (21:27) As you were saying, I was thinking about like when I started my podcast, I was on with my friends and I was nervous recording with my friends. (21:35) I couldn’t even introduce them.

(21:36) I’m like, okay, let’s do that again. (21:37) Okay. (21:37) Take three, take four.

(21:39) And they’re like, we’re just talking like we normally do get out of your own way. (21:43) And you’re right. (21:44) It’s a muscle we’ve got to build and just keep trying.

(21:48) And gosh, I embarrass myself pretty much weekly. (21:52) Now that you mentioned that I’m thinking about what’s the last embarrassing thing I did today. (21:56) So I love it.

(21:58) It’s such good advice. (21:59) Now I want to talk about bold action. (22:02) One of your core beliefs is that the universe rewards bold action.

(22:08) What do you mean by that?

Gregory

(22:10) I mean that if you are willing to consistently get out of your comfort zone, consistently push the edges of what seems normal in your life, the universe is watching and the universe rewards it. (22:24) And I mean this quite literally, both through my own lived experience and through working with hundreds of clients. (22:31) I can’t explain what’s going on, but when you consistently get out of your comfort zone and take bold action, the two S’s start to show up.

(22:40) So you start to see serendipity and synchronicity. (22:43) And going back to the beginning of my story, when I quit my job in finance without a plan, without knowing what was next, that was the first bold action I think I’d ever taken in my life. (22:53) And I had the craziest moment show up, which was as soon as I put my two weeks in, I literally had a stranger on the internet reach out to me to introduce me to another stranger who became my co-founder for the non-profit.

(23:07) Two people didn’t know each other, didn’t know what the other person was saying, but we were saying the identical things. (23:15) We both had the same mission and the same vision, and we wanted to make personal development part of education. (23:21) And we were connected seemingly in this magical way because I was willing to take bold action.

(23:29) And this happens all the time. (23:32) I’ve had so many clients where they finally make the decision that, okay, it’s time. (23:36) I’m ready to leave this career.

(23:37) I’m going to pivot. (23:38) I’m going to go here. (23:39) And I kid you not, within two days up to about a week, they will get a title promotion or they will get a random increase in their compensation that seems to come out of nowhere.

(23:52) So whenever you do take bold action, the universe rewards you, but then it will also test you at the same time to see if that’s really what you want.

Melissa

(24:03) It’s so interesting because it’s so true. (24:06) Doors open when we’re moving, but if we’re not moving, I would say stagnation is blocking the synchronicities from happening because we’re just static. (24:19) We’re not moving.

(24:20) Things can’t come to us if we’re not moving. (24:23) And I love physics, so I love to talk about this kind of stuff. (24:27) So why does stagnation block these synchronicities or momentum attracting an opportunity?

Gregory

(24:36) Yeah. (24:36) I mean, I think there’s probably a metaphysical answer to this and then also a practical one. (24:40) Knowing your audience will kind of stick with the practical nature of it, which is if you are stuck and stagnant, you’re just showing up differently.

(24:49) Your energy is lower. (24:50) You aren’t meeting new people. (24:51) You aren’t getting out there.

(24:53) And I think the actual mechanism behind taking bold action is that you just show up differently. (25:01) You’re more alive. (25:02) You’re starting to tell your friends and your colleagues like, wow, I just did this thing.

(25:04) It’s crazy. (25:05) And they feel the energy. (25:07) And then you are putting yourself out there.

(25:09) So that’s when doors open. (25:11) You meet new people at new times for new opportunities. (25:15) And I think it really comes just down to that momentum piece, is that you are feeling more alive.

(25:21) You are doing things that are new. (25:23) You’re talking about it. (25:24) And people resonate with that type of energy.

(25:27) They want to connect you with someone that they just met. (25:30) Or there’s an opportunity that they think of you for it because you’re in this flow state. (25:37) So that’s kind of the mechanism behind it.

(25:40) And I think that the reason why I’m so gung ho on bold action is because not only does it lead to future opportunities, but just taking bold action to shake things up, to get out of a rut is super helpful. (25:53) It’s the number one tool I go to when working with clients who just feel like they’re stuck and they don’t know what to do next. (25:59) You don’t even have to do the right thing next.

(26:01) You just have to do something that gets you out of your comfort zone.

Melissa

(26:04) It seems so simple, right? (26:07) And as we’re talking about it, it’s just really simple to get out of your comfort zone, try a new exercise, drive a different direction, make a new friend, talk to people you wouldn’t talk to normally. (26:22) But it’s having the courage to do it and just trying it.

(26:27) And then if it doesn’t work, laugh at it. (26:30) I even think about me writing a book. (26:32) It only happened because I said, I was joking.

(26:36) And then someone said, you could write a book. (26:38) I’m like, I guess I can write a book. (26:40) I’m not really a writer, but I could probably put some things on paper.

(26:43) And so synchronicities happen all the time. (26:47) And I’ve seen it in my own life. (26:48) I’ve seen it in hearing your story.

(26:51) I’ve seen it in so many people. (26:53) And so I want to talk about, let’s go after our big dreams. (26:58) Let’s figure out what those dreams are.

(27:01) And so for somebody who’s listening right now and they’re stuck, they’re scared, they’re successful on paper, but they’re empty and unhappy and burnt out. (27:13) What’s the first step towards chasing their dreams without burning their whole life down?

Gregory

(27:20) Yeah, absolutely. (27:21) That’s a really, again, important distinction because no one wants to go on a big adventure if it means that they have to burn their life to the ground and let their family down and not be able to afford anything in their life anymore. (27:33) That’s terrible.

(27:35) So there’s so many different ways to approach it. (27:37) But the short answer is just being curious, starting to ask yourself questions or work with someone like a coach who has frameworks and questions to help you work through this. (27:46) One of my favorite places to start with clients is a Japanese concept called ihigai.

(27:52) It is a intersection between what you love, what you’re good at, what you can get paid for, and what you think the world needs. (28:00) And I love this because no one ever asks you, what do you think the world needs? (28:06) What do you think the world needs more of?

(28:07) What do you think the world needs less of? (28:09) This is a really fun place to start with people. (28:12) And it’s where I start with a lot of my clients.

(28:15) So just familiarize yourself with the ihigai concept. (28:19) I’m happy to take anyone listening through this framework. (28:21) It’s super fun.

(28:23) But then also you can ask yourself some fun questions like two that I’ve come across recently that I love using as a starting point. (28:30) One is, if your life was a movie, what would the audience be screaming at you to do right now? (28:37) What action do you need to take?

(28:39) What do you need to stop avoiding? (28:41) That’s a really good one just to kind of jar people out of the current existence or take them off autopilot. (28:47) Another question that’s really fun is asking, what would my 85-year-old self look back on and be most proud of?

(28:57) This helps because our 85-year-old self or 95, however, what age you want to go to, they’re probably wiser than we are currently. (29:05) And they probably have a more holistic view of our life and what was important. (29:09) And so simply future pacing to that, and then trying to look back at the current situation now can sometimes really help you figure out what needs to happen next.

(29:19) And I’ll also say, it’s hard. (29:22) It’s really, really hard to figure out what do I want? (29:25) What’s my purpose?

(29:26) How can I bring more meaning and fulfillment into my life? (29:29) And that’s also why I love bold action because it takes no skill whatsoever. (29:33) You literally just have to move your body through space and time into a situation that feels unfamiliar and maybe open your mouth and ask a stranger if you can give them a hug or something.

(29:42) But it’s difficult work. (29:44) And it’s also the most important work that you can be doing. (29:47) Going back to that question of why do people avoid meaning for so long, knowing that it’s the top regret of the dying, knowing that if you aren’t living a life true to yourself, you’re literally on the fast track to getting to the end of your life and saying, oh shit, I messed up.

(30:03) I don’t know if I’m allowed to say that. (30:04) That’s what really lights me up. (30:05) And it’s been a really interesting journey for me as a coach because at first I was like, I want to help everyone.

(30:12) Everyone has a dream. (30:13) And then it was like, okay, I need to niche that down. (30:16) And what I’m realizing, the people I love working with the most are those who are highly capable, highly competent, and they’re successful on paper.

(30:25) So they are at the highest risk of spending their entire life living someone else’s dream. (30:30) Just continuing to show up in their director or senior director or vice president role and just keep doing things for the company and achieving. (30:38) And they’re in their zone of excellence.

(30:40) They’re really good at what they’re doing, but they don’t necessarily feel alive. (30:43) They’re not in their zone of genius. (30:45) I love helping those people figure out what’s next.

(30:48) And that could be a lateral move within the company. (30:51) It could be moving to a different company. (30:53) It could be leaving corporate entirely and starting their own thing.

(30:56) I am obsessed with helping people figure out what is the life that feels most true to me and how can I do that? (31:03) How can I remove all the obstacles that are between where I am now and where I would be if I was fully aligned? (31:10) Because that’s how we become fully alive.

(31:13) If I had to boil down everything I do into a single sentence, it’s that I help people become alive.

Melissa

(31:21) And you know, I love that because we are all so alive no matter what’s happened and where we are, but time and fear and struggle and pressure and burnout and excuses and everything that goes, it builds and builds and we develop these layers upon layers upon layers. (31:40) And so we really have to break through with exactly what you’re talking about to redesign our identity safely. (31:50) And I know for me, my identity is, the core values of who I am are the same, but what I’m dreaming and what I’m going after and who I’m becoming and what experience I have, they’re changing every single month all the time.

(32:04) So what I wanted for 2025 is night and day different than what I want for 2026. (32:12) And I’m sure it’s going to be different in 2027. (32:14) And so for those listening, how do they, you know, back to the fear we were talking about, you know, how do I start?

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Gregory

(33:26) Yes, yes. (33:27) For anyone listening to this, reach out to me. (33:30) We’ll put my email in the show notes because I’m currently off social media, but I have a whole process.

(33:35) I call it defining your identity. (33:37) I have this thing called the better self blueprint, and it is figuring out who you want to become. (33:42) That’s the first step.

(33:43) Who do you want to become? (33:45) Create a vision. (33:46) And then what do you need to do?

(33:48) What daily habits can you start taking to become that person? (33:52) James Clear, who’s a famous personal development author says that every action you take is a vote for the identity of the person you wish to become. (34:00) And that’s why I’m so big on helping my clients shift their identity, because identity determines everything and you can shift the identity through small actions.

(34:11) So that’s really the starting point is just to really simplify it. (34:15) Start getting curious. (34:16) Start to notice, oh, wait, hey, maybe I don’t love my life right now.

(34:21) Maybe I’m not fully happy with what I’m doing. (34:23) Maybe I’m a little burnt out and overwhelmed, and I don’t particularly like being on back to back meetings for eight hours every day and then expected to still get all this work done. (34:34) And if you’re in that space, don’t beat yourself up for it.

(34:38) I love what you said around we’re all alive. (34:41) We’re all so alive. (34:43) But modern society, especially a lot of the corporate lives we live, just cake on this mud layer after layer of this mud that’s getting in the way of our aliveness.

(34:54) And over time, that can wear you down. (34:57) So starting to recognize, hey, I might not be exactly where I want to be, and that’s OK. (35:02) And then getting curious and starting to ask those questions of what do I want?

(35:07) Who do I want to become? (35:09) And what might I do to start becoming that person?

Melissa

(35:12) And, you know, for me, it was also a feeling. (35:14) So I didn’t realize there were people that I was working with every time I was around them, like my entire body would get tense even before they said a word, even before we did a thing. (35:25) My whole body was tense and I was just irritable.

(35:28) They didn’t do anything. (35:31) It’s just a feeling that started to happen. (35:33) So sometimes it may be a symptom, but sometimes it may just be like, I can’t stand being around this person.

(35:39) And you got to redesign your life to get away or, you know, manage as much as you can, how much interaction you have with a person, maybe not get on a call. (35:49) Like for me, what I chose to do was not have calls. (35:52) I chose to move the communication to email.

(35:54) And so I could send it unemotional and receive it unemotionally. (35:59) And so for me, back to what you were saying about mud, that mud of having to deal with people I didn’t want to deal with, the constant, you know, blame game that this person had or the credit they were taking that wasn’t theirs, it’s mud that we pack on. (36:15) So we get irritable, we have resentment, we have frustration and anger and all those kinds of low vibe emotions that we can’t feel high vibe when we’re in a place of fear, resentment, anger, frustration, whatever those words are.

(36:32) So for me, you know, it was, it was a feeling too. (36:36) And I had to unpack what I didn’t like, and I couldn’t put my finger on it. (36:41) It took me some time, Gregory, to figure out.

(36:45) I’m like, okay, I had to audit my own life. (36:47) And I just, I had to like, how is Melissa feeling today? (36:51) What is no longer fitting?

(36:52) Okay. (36:52) It’s that person in this situation. (36:55) And I had to name it.

(36:57) I had to talk about it’s the person it’s their energy. (37:00) It’s the way they talk to me. (37:01) It’s the way they behave.

(37:03) And then I had to move it. (37:04) And then I had to redesign forward on what I can control, not backwards.

Gregory

(37:12) And I was just going to say, I absolutely love how you’re sharing that because that is the answer. (37:19) I will add on to what I said earlier about getting curious. (37:23) You need to create space.

(37:25) And you were just mentioning there, you were creating space to unpack what you didn’t like about the situation about the person, because feelings and emotions are difficult to discern at first. (37:36) A lot of the time we have this gut feeling. (37:38) We don’t really necessarily know what it means.

(37:39) We’re getting frustrated on calls. (37:41) Like why is that happening? (37:42) So creating space to start unpacking and getting curious about what’s going on, I think is actually the answer to the question you asked earlier of where to start.

Melissa

(37:52) Yeah. (37:52) And you have to pause and we’re in a hustle culture. (37:56) It’s faster delivery, quicker things, more money.

(38:00) We have more money than we’ve had as a world and a country. (38:06) And we’re the most unhappiest we’ve ever been yet. (38:09) We have faster, better technology.

(38:10) We’re making more money in theory, but we can’t reinvent and redesign if we don’t pause, reflect, choose differently without validation from other people who in some cases don’t deserve to have input into your life. (38:30) Like for me, those people that I was giving the power to did not have the authority to give me permission to make a choice or to start a podcast or to write a book or to take a day off to hang with my kids. (38:43) It’s our internal authority that we give ourselves and knows that we love.

(38:50) So what we’re talking about today is a very different kind of leadership, a very different kind of success, one that fills your soul, gives you more energy and brings the life that you’ve always dreamed of that really didn’t think that you could have. (39:08) And so it’s really dreaming big and putting it out there. (39:12) So, so much to talk about with you.

(39:14) I have like a hundred more questions. (39:16) So I want to do this fun because I think it’d be so fun with you. (39:19) I’ve been doing these little lightning rounds with people.

(39:22) I’ve got to do it with you because I have so many quick questions and the only way to get through them is just to hammer them with you. (39:29) So one fear that holds people back.

Gregory

(39:33) Fear of what other people will think.

Melissa

(39:35) One lie society tells you about success.

Gregory

(39:39) Oh, I mean that it’ll make you happy. (39:41) That’s obvious.

Melissa

(39:43) One belief that creates courage.

Gregory

(39:47) I will be okay no matter what happens.

Melissa

(39:51) One habit that kills dreams.

Gregory

(39:56) Procrastination, putting it off.

Melissa

(39:59) One risk that’s worth taking.

Gregory

(40:02) Most all of them.

Melissa

(40:05) Yeah, it’s so true. (40:09) One regret people don’t admit.

Gregory

(40:13) That they are living someone else’s life and that they feel like an imposter.

Melissa

(40:19) One rule you live by.

Gregory

(40:23) That the universe rewards bold action.

Melissa

(40:26) I almost guessed that one. (40:28) One sentence people need to hear today.

Gregory

(40:32) The number one regret of the dying is I wish I would have had the courage to live a life true to myself, not the life others expect of me.

Melissa

(40:41) This has been such a blessing to talk to you. (40:44) Thank you so much for your time, your good work, your heart, your knowledge, and all that you’re doing out there in the world to make people live these big, bold, wonderful lives that they only imagined in their dreams. (40:56) Any final thoughts that you want to leave with our listeners and the best way to connect with you if they want to learn more about the good work you’re doing?

Gregory

(41:04) Best way to connect with me is my website. (41:06) We’ll put that in the show notes, www.GregoryRussellBenedict.com. (41:11) You can check out my TEDx talk titled, How Being Bold Will Change Your Life.

(41:16) The top comment on the talk is, I thought this said how being bald will change your life. (41:20) So you can go read the comments and have a good laugh. (41:23) What I want to leave people with is I get it.

(41:25) I get what it’s like to be overworked, underslept, tired, burnt out. (41:31) You’re really trying your best to show up and achieve all these things that you actually genuinely think will make you happy. (41:38) And you get to go on the journey to find out whether those things will make you happy, whether that’s true or not.

(41:43) But give yourself some grace, create some time to slow down and have that pause, like Melissa and I are talking about. (41:50) In that pause, in that curiosity around, is this really what I want to do with my life? (41:55) Is this what I want to do for the next 10 years, next 15 years?

(41:58) That’s where a lot of the magic and your answers will come from. (42:01) So start small, get curious, and you got this.

Melissa

(42:05) Thank you so much for being here, my friend. (42:07) That’s the Executive Connect podcast.