Success is Yours to Define – Why Are We Still Doing That?
No Vacation Required
Updated 9/2026
Have you ever felt like you're winning on every level, only to realize you're completely losing at the things that actually matter to you?
We’ve been there.
In fact, about ten years into our relationship, we were “hyper-trad" – upwardly mobile, making good money, and receiving constant accolades. But we rarely saw each other.
When we finally admitted to friends and family that the constant travel and demanding schedules were draining us, their response wasn't sympathy. It was excitement over how "important" our jobs were.
That was our first real schema break.
This week, we are diving into the "L" in our L-I-F-E philosophy: Letting go of preconceived notions of success. Whether it's your career or your relationship, it is entirely too easy to internalize the "dream of the planet" and let external metrics dictate your happiness. The good news is that you get to decide what success looks like.
Onward and Inward,
COMMON QUESTIONS ANSWERED IN THIS EPISODE
❓Why do I feel guilty for having personal career goals? Many people feel that having internal, personal measures of success is like "cheating" on their company. In reality, having your own KPIs separate from corporate objectives makes you more effective and protects your long-term fulfillment.
❓How do you know if your relationship is actually successful? A successful relationship isn't defined by external markers like wealth, status, or grand romantic gestures. True fulfillment in a relationship is found in the small, everyday moments and the ability to navigate tough times together as a team.
❓What does it mean to "let go" of success? Letting go of success doesn't mean abandoning your ambition. It means letting go of other people's definitions of success – the cultural script that tells you what a "good" career or relationship is supposed to look like – so you can write your own.
❓How can I start defining my own success? Start by asking yourself, "Who is this for?" when looking at your goals. If the answer is your boss, your parents, or your social media followers, it might be time to pause and establish what truly matters to you personally.
CHAPTERS
(00:00) Why are we still doing that?
(01:00) Letting go of the "Dream of the Planet"
(02:44) Why you need your own secret career KPIs
(06:12) Our relationship wake-up call
(12:15) Breaking the schema of traditional success
(14:39) Why the small moments matter most
(18:07) The Cabo Bridesmaids and "Marrying Up"
SUPPORT NO VACATION REQUIRED
If this episode resonated with you, please leave a review on Spotify, Apple Podcasts, or YouTube! It is the best way to help our message reach more people.
✅ Never miss an episode by hitting the follow button on Spotify, Apple Podcasts, YouTube or wherever you listen to podcasts
✅ Read The No Vacation Required Book
✅ Follow us on Instagram
✅ Talk To Us
LINKS AND RESOURCES
🔗 Our commercial for Washington State Tourism
🔗 Searching for Meaning at Work Could be Making You Miserable
🔗 Why Are We Still Doing That?
🔗 Success Is Yours To Define
TRANSCRIPT
Kent (00:02)
Welcome to the No Vacation Required Podcast where each episode we ask, why are we still doing that? Building a life you don't need a break from starts by letting go of templated ideas of success. And letting go of templated ideas of success requires each of us to ask, why are we still doing that? Why are we still doing that? To the actions we've put on autopilot in the interest of pleasing family, fitting in with friends, and aligning with the dream of the planet.
Kent (00:31)
Welcome to the No Vacation Required Podcast.
Kent (00:34)
Where we talk about why are we still doing that? And this is so fun because this is something we've been wanting to do for a long time. Because some of the things we want to talk about are things that even with each other, we're like, Yeah, why are we still doing that? Why are we as people still doing that?
Caanan (00:52)
So this is our soapbox.
Kent (00:54)
This is our soapbox. Yeah. So interestingly, last time around we talked about invoking your agency. And we heard a lot from people and clients saying, Yeah, that sounds great, but I don't even know what I stand for. So I don't know how I can invoke my agency very effectively when I just numb out and go along.
Caanan (01:17)
Yeah, it's kinda hard to stand up, stand tall, speak out when you don't know what you stand for. So the feedback was that was interesting. Not surprising, but interesting.
Kent (01:27)
Yeah,
Kent (01:28)
well well I I can't remember if we told you or we didn't tell you that we skipped a very important step because we were very much wanting to talk about invoking your agency, and that's the I in our life, L I F E philosophy. We just breezed right over the L and the feedback we got tells us how important it is to talk about that L and the L is let go of preconceived notions of success.
Kent (01:58)
let go of the dream of the planet as it applies to what a successful career looks like or what a successful relationship looks like or a successful day or meal or whatever. So yeah, in order to invoke your agency, you have to let go of these ideas of success that are so ingrained in us. So in that first or in this first post, because we have a accompanying blog post which we can link to
Kent (02:27)
Where we introduce this idea that success is yours to define. And since so much of the work we do is with individual people and their career growth and development and work groups, this first post is about better careers. And let me just say here that there are five... five areas where people really want to improve their lives.
Kent (02:54)
And of course, we say you first have to let go of others' ideas of success. So the first one, the biggest one, the one we work with the most is people want better careers. So that's what we wrote about. Caanan, I know you have a lot of thoughts based on the feedback we got and just the work we do with clients. What do think is the most interesting part of that? Or, you know, what have we what have we had the most "oh wow!
Kent (03:22)
I never thought of that!" feedback ...
Caanan (03:24)
Yeah. We give some pretty good tips in this post. So do go read it if you haven't had a chance to. But one of the tips that I think is most profound and the people are most surprised by is our tip to have your own measures of success in your career. Essentially not personalizing or internalizing or assimilating the company's goals as your own. This is a foundational
Caanan (03:54)
piece of our focus on workism, another thing you can go check out if you haven't read about it already. But this idea that you can focus on achieving the corporate goals. You need to do that. We're realistic. You're realistic. You need money. You need to stay in this job. But you don't have to make those goals your own. You don't have to completely become subservient to the corporate objective. What you do is
Caanan (04:22)
focus on achieving those goals, but internally, secretly, you have a completely different set of KPIs and they are personal to you and it really doesn't matter if you hit the corporate goals as long as you're hitting your internal KPIs.
Kent (04:40)
Two interesting things come to mind with this. It's so interesting what you're saying. I think of all the times when we're doing intake with individuals or teams and we talk about you know, what is what are your goals? What what's your goal on your team? And people are very quick to talk about their goal as defined by their company or their leader. And then when we move to the next question and say, Okay, so how about your personal goals? Their eyes get big like
Kent (05:09)
I can't say that out loud or I can't tell you what I'm really doing here for myself. I mean, oftentimes people have never thought of it and it's a big goose egg nothing, but oftentimes they're looking like, Don't ask me that question.
Caanan (05:25)
Yeah, I think there's a whether or not people can articulate it, there's a feeling like having internal goals, having your own personal measures of success is like cheating on your company. And it's just the opposite. Like you you can be more effective in your career, which is important if you have your own measures of success that are completely separate from the company's objectives.
Kent (05:53)
Yeah, we often ask that question, Who is your career for? And people are like yeah. Not for my company, ultimately for me.
Kent (06:10)
We are talking about measures of success, and there's big five things. People want better careers, better relationships, more time, better health, and more money. So this is gonna be a multi phase couple podcasts. As we mentioned, we wrote about better careers in
Kent (06:36)
our most recent post. And for the bulk of this podcast episode, we're talking about better relationships. This is something, you know, that's in our professional realm over the last few years as we've pivoted to helping people with the personal side of their life and couples with their personal life. And it's something we have a lot of experience in.
Caanan (07:01)
We don't talk about it much now because it's been a minute, but the first ten years of our relationship we were very much aligned with – Kent use the term earlier – the dream of the planet. We were hyper trad.
Kent (07:15)
yeah. Hyper trad. Never seeing each other.
Caanan (07:20)
We rarely saw each other. We were intensely upwardly mobile in our careers. Yeah. We were essentially like winning on all levels except for
Caanan (07:30)
what ultimately mattered to us, which was spending more time together. So you actually have you have a good example of what our life looked like at the time. Yeah well I
Kent (07:41)
To say too, this is something we talk about a lot because this realization 10 years in about a relationship also coincides with the launch of No Vacation Required. yeah. So reading previous blog posts, and if you pay attention to or go back to our previous podcast, Stop Hating Mondays, we talk about pieces of this story at different times, not so much the relationship side,
Kent (08:09)
which we're getting into now and how we had to define for ourselves what's a better relationship and how unbeknownst to us at the time, it starts with asking why are we still doing this? Why are we measuring the success of a relationship based on what other people think is the success of a relationship, which is barely seeing each other, complaining about each other when they're not together. That one always gets me you know yeah. So much friend group time
Kent (08:38)
Talking about all your grievances with your partner or your spouse. So we had to ask, let's start prioritizing our relationship and not making it fifth, sixth on the list. You know, if you've listened to those prior podcasts or the blog posts I referenced, we talk about the only time we would see each other is when we were doing training runs
Kent (09:04)
before a marathon we were training for. The Paris marathon. So we're getting up it in the middle of the night practically in order to do these big training runs before the Paris marathon.
Caanan (09:14)
I just wanna interject here because you're gonna get into this, but to your point about external measures of success, our rarely seeing each other for those ten years, but making good money and getting promotions and accolades from our employers, our friends and family viewed that as a good relationship. Yeah. Yeah. Even though it was actually anathema to our being connected.
Kent (09:43)
Yeah. So setting the stage. Setting the stage. I Kent had just gotten a new job that we knew Caanan and I knew was going to be very training heavy at first with lots of travel, with I think a couple three months of tons of travel to quote unquote get up to speed. Well, many months after that, and that was stressful kind of being away most every week, and sometimes for two weeks at a time.
Kent (10:13)
I had a certain degree of success. So plans changed and my need to travel also ramped up. Which wasn't a huge problem, but it became very last minute. And I'll never forget there was a particular Friday where I found out I had to be in Chicago on Monday. And this had this kind of thing had happened a few times before and it was like, my gosh, like no.
Kent (10:43)
But the telling part for us, found this out on Friday. We had plans with friends and family all through the weekend. So our droopy faces around our family and friends were a giveaway. And we started to talk with them about the hardship of this and wasn't hurting our relationship, so to speak, because we're we've always been very strong. but it was an unwelcome kind of bother and
Kent (11:14)
We noticed rather than being sympathetic to us for mentioning that this wasn't great for our relationship, all these people wanted to talk about was how exciting it is that I had such an important job that I needed to be in Chicago on Monday.
Caanan (11:33)
Yeah. Like you'd won the lottery by having this disruptive travel schedule for work
Kent (11:40)
Well, it's like you said, like our friends and family saw this as a sign of success. So yeah, we're sitting there having brunch. in this bustling place, confiding this discomfort and feeling like this is surreal. These people are more excited about the thrill of this job than they are that we've just told them.
Kent (12:02)
that this is really starting to drain us on a personal level.
Caanan (12:07)
Yeah.
Caanan (12:07)
And it's as you said earlier, it was a critical point for us, a schema breaker, if you will, because here we're sharing something that we feel is I'll just say unhealthy for our relationship. Our inability to plan, our inability to spend time together, how disruptive this job was, despite being high paying and
Kent (12:30)
All the things
Caanan (12:31)
Those things, though all those traditional measures of success. Yeah. you were very successful in this job, but it wasn't the right thing for our relationship. And recognizing that people didn't understand that. They could not connect to what we were saying. Like this job is not healthy for us was a huge schema breaker. And what started our no vacation required mindset. Go ahead.
Kent (13:00)
Yeah. So we always talk with our clients about these inflection points because those were our first signs, like, wait a minute, something's weird here. So that time where we were like, we don't have to look at relationships like everybody else did. Yeah. In fact, that everybody's so excited that we're stretched in this way for all these great reasons, these great jobs. Mm mm.
Kent (13:29)
We need to look at this. So one of the first times we asked, why are we still doing that? And we said, Huh, we're not gonna do it anymore. So yeah, tried to remedy that situation. They had a different plan for me in this upwardly mobile fashion than I had. And because Caanan and I had decided why are we still doing this? We have new measures of success regarding our relationship. We
Kent (13:59)
Turned the corner. So here we are a decade plus after that, and we are living these nuanced, individualized definitions
Caanan (14:11)
Yes.
Caanan (14:12)
It was a really important moment for us that entire period of our life, as I said, having our schema broken, recognizing that what we wanted for ourselves in our relationship was significantly different than how a successful relationship, was defined externally. And the way we now measure success and have for quite a long time now
Caanan (14:38)
in our relationship turns out to be fairly disruptive. I'm thinking about the fact, and this is exciting to bring up.
Kent (14:46)
What?
Caanan (14:48)
Our can we talk about our commercial? Yes.
Kent (14:51)
Okay. 'Cause we talk about this
Caanan (14:54)
Yeah. So we recently had the opportunity to do a commercial for the state of Washington, which if you know us, you know we're big Washington State fans and nature fans. And so this was pretty much a dream come true for us. This commercial turns out to be kind of documentary style. Yeah. Less so about the state and more about how
Caanan (15:23)
our relationship and how we move in this state, but it was pretty fun because we got to talk about our take on relationship
Kent (15:33)
our definition of success.
Caanan (15:35)
what success looks like in a relationship.
Kent (15:37)
And Canaan, what did you tell the people?
Caanan (15:42)
That the traditional ideas of romance and relationships are really backwards. That and this is coming from two guys who have a lifetime of big life changing moments.
Kent (15:58)
Yes.
Caanan (15:59)
Big once in a lifetime moments. Those are not what make for a great relationship. In fact, they are
Caanan (16:10)
secondary and sometimes in contradiction to the true measures of an effective relationship, which are the little moments. And there's a point in the commercial where Kent says something truly profound, if I don't say so myself, where he says, I think what do you say? It's in the small moments. It's here. It's here.
Kent (16:34)
Yeah,
Kent (16:34)
I'm basically saying that it's there's no grand trick to a healthy relationship, which is what everybody wants to know. That in fact our definition of a successful relationship is in all the little moments. And we say, Yeah, it's here, it's here. Meaning it's right now in this moment, it's right now in the next moment, it's in the moment right in front of you, and those are usually
Kent (17:03)
the small moments. And Caanan goes on to say that having that kind of connection and appreciating all the moments then makes it easier when the tough times come along.
Caanan (17:17)
Yes, that the tough times become romantic because you get to go through those times together. And to that point, I just want to say that that moment where we both realized ten years into our relationship that
Caanan (17:32)
the way we were focused on our careers, our upwardly mobile idea of success.
Caanan (17:41)
When we both realized that that no longer held value to us and collectively decided to do something about it to make a bold change and redefine relationship for ourselves, that is probably one of the most romantic things that's ever happened in our life, and that is the sign of a good relationship.
Kent (17:59)
For sure.
Kent (18:06)
So the bottom line here is that you get to decide what success looks like. Success in work, and as we just talked about, success in relationships. Funnily we the regarding the relationship thing, we talk about the Cabo girls. Cabo
Caanan (18:28)
The Cabo girls!
Kent (18:28)
girls. Yeah, we were in Cabo on vacation.
Kent (18:35)
and there's a big wedding happening and all the bridesmaids were hanging around by us at the pool one day and like woke us up to ask us what this one should do regarding this, you know, guy she was dating who they defined as a loser. And we were saying, like, well, why were you s why would you say this guy's a loser? It was completely based on a job. He doesn't
Kent (19:02)
have a job that's good enough for Molly or whatever her name was.
Caanan (19:08)
Yeah. It was extraordinarily basic in terms of measuring somebody's worth.
Kent (19:15)
So we gave these margarita fueled
Kent (19:19)
these girls were drunk
Kent (19:20)
flight attendants from Atlanta the lesson of a lifetime and they really appreciated it. And they said like, We have never heard this before because our parents are insistent that we only marry up. We only marry successful and that is
Kent (19:43)
defined by a job. So we're here to tell you you better ask, why are we still doing that? Because you get to decide what your measures of success are.
Kent (19:56)
Thanks for joining us for this episode of the No Vacation Required Podcast. If you want a life you don't need a break from, a life where you live from a place of commitment and not comfort, join us for regular new episodes where you can always count on us to find a tired tradition and to ask, why are we still doing that?