Always Searching For The Next Thing – Why Are We Still Doing That?
No Vacation Required
Updated 9/2026
If you’ve ever found yourself sitting on a metaphorical (or literal) beach, wondering why you're already stressing about your next move instead of enjoying the view, this episode is for you.
Today we’re diving into a trap we all fall into: the endless pursuit of "what's next." Inspired by a hilarious offhand comment Neil Patrick Harris made about trying to get into Madonna's exclusive post-award show party (only to find out there was another secret party inside), we’re breaking down why external milestones never quite deliver the peace they promise.
Why are we still chasing the next level, the next trip, or the next promotion, only to feel exactly the same once we get there?
Onward and Inward,
COMMON QUESTIONS ANSWERED IN THIS EPISODE
❓Why does achieving a goal rarely bring lasting happiness? Chasing external milestones often leads to the "next level" trap, where reaching a goal only immediately sparks the desire for the next one. True fulfillment cannot be found in external validation because it is fleeting and doesn't provide a grounded sense of peace.
❓How does social media fuel the "what's next" mentality? Social media serves up the highlight reels, curated moments, and big adventures of others. This conditions us to always crave something different from our actual life – no matter how good – making it difficult to appreciate the current moment.
❓Why is it so hard to be present in the moment? Our culture places a high social currency on future plans and past achievements, often ignoring the present. This constant conditioning makes simply "being" feel unproductive or boring, driving us to constantly seek out the next distraction.
❓How can knowing yourself help you overcome FOMO? When you truly understand your core values, strengths, and personality, you can evaluate your cravings objectively. Instead of blindly chasing what society tells you to want, you can confidently ask, "Does this actually matter to me?"
❓Why do the smallest moments often bring the most fulfillment? When you strip away the noise of external expectations, you often find that simple, intimate moments – like lingering over coffee or sitting in the sun – bring the deepest joy. These moments are entirely within your control and don't require external validation.
CHAPTERS
(00:00:00) The Illusion of External Fulfillment
(00:00:53) There’s Always Another Level
(00:02:11) Why We Stay on the "What's Next" Cycle
(00:05:18) The Social Currency of Future Plans
(00:08:05) The Cinque Terre Boat Tour
(00:18:46) Tips for Breaking the "What's Next" Cycle
(00:24:51) The Paradox of Fulfillment
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TRANSCRIPTS
Caanan (00:00)
I love the topic of this episode
Kent (00:03)
I do too.
Caanan (00:04)
because it's something that we experience ourselves and we see so much in the people we work with and of course friends and family. Yeah. And it's something that I know you out there have experienced in your own life and would probably like to not experience it anymore because it's so silly. And that is this idea that fulfillment is external –
Caanan (00:29)
that can be found externally. And that fulfillment is something that can be found essentially as we say in the post, over there instead of right here where you are right now. Yeah. And I love that we open that post. If you haven't read it, go check it out
Kent (00:48)
It's called There's Always Another Level.
Caanan (00:51)
There's always another level. Yes. I love the story we opened with, which is this thing that Neail Patrick Harris said in a movie we just watched called Group Therapy. Sort of an off-handed comment he made about trying to get into these exclusive post-award show Hollywood parties.
Kent (01:10)
Yeah, actually trying to get invited to a party first. And how each year this becomes more and more of a challenge.
Caanan (01:17)
Yes.
Caanan (01:17)
And it was laughable because as you just said, every year there's a new party, there's a new level, there's something more exclusive to get into until he ultimately gets invited to Madonna's party. Only to find out that once you get into Madonna's party, there's still another level, which is a sub party where Madonna actually is. Yeah. So I just thought that was such a clever way of getting to this point of searching for
Caanan (01:47)
fulfillment in the next thing because as we're all so aware, the next thing never brings the fulfillment you anticipate it's going to deliver.
Kent (01:57)
Yeah, just in the way that the current thing didn't bring that level of fulfillment, which is the whole reason you were striving for this thing. Exactly. And it then just becomes the next thing. This is such a meaty topic for us, almost too overwhelming because it's at the heart of so much of the work we do and so much of the life we live in terms of the work we do with individuals and
Kent (02:26)
Companies and work groups – so often the perceived problem, you know, because we're always kind of solving for a problem, helping somebody grow or help a team grow. And the problem is like, I don't want to talk ourselves out of a job, but there's not a problem. In this post that Caanan was just referencing, we talk about a client who just got a promotion and then is already wondering if it's too early to be angling for another promotion. And
Kent (02:56)
This is the problem, the why are we still doing that? And I can tell you why we're still doing it. It's because institutions, companies, the institution of late stage capitalism, the institution of social media, the institution of FOMO keeps you in that mindset. So, you know, people will sit down for our introductory meeting
Kent (03:25)
And we're ready to hear something completely devastating. And it's sort of like, okay, Kent and Caanan even though we changed this yesterday, now we want to change this by tomorrow. What do you think? How are we gonna get there? How are you gonna help? And we're like, the honest answer is you can't stay on this cycle. You know, you you in some ways you have to to meet corporate shareholder demands. And
Kent (03:54)
boss demands and you know, we we're not suggesting you live outside of reality, but as we say in so many episodes of this podcast, you can have your internal reality, which we call the truth, and still contend with the external reality, which are all these factors that you can't change. You know, you we understand you can't change what your boss is saying you need to do to get to the next level.
Kent (04:24)
But you can change how you view these things, and therefore you can begin to change the narrative.
Caanan (04:32)
Yes, you can stop believing the lie, and we all know it's a lie because it never pans out the way we think it's going to. The lie that the next thing will be the thing that is fulfilling. Even though, as I just said, you that's what you thought the last time. Yeah. And then you get to the present moment and you're already longing for the next thing. Yeah. But we don't stop and say, wait, I thought the jacket I just bought
Caanan (05:02)
was going to be the thing that made me happy. I thought the trip I just took was going to be the actually not the trip I just took, the trip I'm on be the thing that makes me happy. And yet I'm sitting here in a pool chair longing for something else.
Kent (05:17)
Yeah. We just had this kind of bizarre moment to flip over to the personal resonance of this, just talking about how we were with another group of friends recently and we're always blown away by how we can all be living these kind of rich lives. And we I mean, while we're arriving is the only time spent acknowledging what's just gone on.
Kent (05:47)
And everybody's got these rich layered stories to share about the now or the this just happened. But somehow the conversation swirls to so where next or what next? Or what's your next move? And we kind of look around and and and see that so much of this conditioning, of course, comes from social media because that's you're just scrolling through social media and seeing these kind of dream scenarios and people
Kent (06:14)
Talking about the what next or the contract or the whatever. And we find it gets comical. Like, wait a minute, are we really not gonna talk about the fact that you know, so and so right here was just on a a 30-day trip to wherever, or so and so just served on this amazing speaking panel. We're gonna just act like that didn't happen and it doesn't matter.
Kent (06:44)
And now we're gonna talk about what's next. We're excited about this episode and we had a really funny, not funny, kinda sad, travel experience pertaining to this topic that we're eager to get into.
Caanan (06:59)
Yes, and I just wanna point out that what you were saying about our our personal social situations is so true, but it it also isn't just what happened versus what's coming next. We're together with friends in a moment and you know what it is never about? The moment. We're never just there. Yeah. Rarely. We are
Kent (07:25)
Or rarely. That's
Kent (07:28)
my yeah that's my carve out in case somebody's listening, like the losers. I'm so we've we have to have a carve out.
Caanan (07:35)
I'm being a little hyperbolic, but yeah, you know, it so often is a catch up of what happened and then as you pointed out, quickly moving on to but what's next? What's next? What's next? And it's it's never or so rarely like what's right now us together.
Kent (08:04)
So whenever we start getting these people wanting to go to the next level in a bad way, vibes on a work project or in a personal life, we have a core memory that we invoke so that we can get on the same page. Yeah. And that core memory is literally it's so hilarious that if it wasn't so hilarious, I would be crying. It actually reminds me of an episode of The White Lotus.
Kent (08:32)
it's so like White Lotus-y it is. Yeah. So a few years ago we're at a dream destination of ours, a place we'd been before. We're huge, huge hiking fans, we're huge, huge Italian food fans, we're huge cute village fans. So you know we love a place like Cinque Terre. So we had returned to the Cinque Terre – Was this our second or third time there?
Kent (09:00)
Yeah, in a jaunt around Italy, we we decided to go back. And this time we did something we're rarely gonna do because tap back to what I just said, we are big hikers, we like to be on our feet. We're like, we're gonna experience Cinque Terre like every which way we can, and we're actually gonna do the boat tour. We're gonna do the boat tour that starts on one end and does a sail around the
Kent (09:29)
the bay or whatever so that you can see all the villages and you're having like little snacks and we're like, we're gonna do it. We're gonna it's so not us, but we are so enamored with the Chinquatera that we're gonna do that.
Caanan (09:44)
Yes.
Caanan (09:45)
That's how you know we're enamored with a place. If we're doing the bow tour this is an insight into our personality.
Kent (09:49)
Yeah.
Caanan (09:55)
I get sick on boats and we just don't do these kinds of tours, but we're so charmed that we're we're gonna do the boat tour. Yes.
Kent (10:03)
We're on the sewer, it's relatively small, doing the obligatory meeting and greeting everybody. And a woman, part of a couple, is fascinated that we have this life centered in travel and giving back and trying to help people in work groups be more fulfilled. That's good news. Extreme interest in other people. The bad news is she cannot.
Kent (10:32)
Shut. It. off. So we're on the store, just getting away from the pier, whatever. And I'm having those feelings like, no, this woman's not gonna stop. And a lot of times with us, because we've been a lot of places, people love to tell us every place they've been. Have you been here? Have you been here? Have you been here? Have you been here? Like it's a competition that we don't want to participate in. I
Caanan (10:59)
I just wanna jump in here and say that unfortunately most of the time these conversations are not about interest in us. It's about setting up a an opportunity for somebody to tell us all of the places they've been and start that weird competition thing which we are just we're not into at all.
Kent (11:19)
Yeah. But yes, and now we're well into this. Well, it's just a couple hour little special thing. We're fifteen, twenty minutes in and this woman is literally not being quiet. And Caanan and I are having a we want to enjoy this right now. Phones down, eyes open, deep gulps of sea air taken in.
Kent (11:49)
A moment. And we're pulling away like take the hint. And of course, as so many people are today, because we're just conditioned to be that way. Back to the first segment. She finds a place we haven't been and then starts the hard sell. you've got I can't even remember where it was. It doesn't even matter. But it's not that we weren't.
Kent (12:16)
Interested, we were just trying to be appropriate. Like, look at the Cinque Terre! We're now by the second village. Let's enjoy that. We're giving those vibes. No way. She is not taking that as an answer. She thinks we're unconvinced about this place she thinks we need to get to. So she whips out the phone and the photos and starts going through the photos of this extraordinary place. And I honestly can't remember what it was.
Kent (12:45)
To convince us that we need to get to this extraordinary place.
Caanan (12:49)
doing the full timeshare.
Kent (12:52)
Yes.
Caanan (12:54)
Yeah. Presentation. You need to experience this. Yes, because yes, she's so enamored with this place that is not where we are right now, which is the Cinque Terre – a dream destination – that she wants to occupy all of our time to sell us on this destination.
Kent (13:17)
Yeah. And I I think finally, you know, we never want to be be rude. And this woman was really sweet to us and we appreciated that she was, you know, kind of trying to come off like she was interested. And one or the other of us said, Hey, let's go to the back of the boat for a a better view. So we were able to break it up. But it was an incredibly frustrating experience. And we always take these moments – whether it's one of us as an individual or as a couple –
Kent (13:46)
Where we look inward before we start pointing the finger at everybody else. And it just made us realize we never want to be these people who who don't want to honor the now or the something that somebody just did that they want to talk about. And in this case, with this Cinque Terre boat tour, it was the now. And honoring the past, honoring what somebody wants to bring to the table and talk about is so important and a great way to
Kent (14:14)
be more mindful of honoring that is to honor the now, whatever the now is that you're in. Because whatever it is, you got yourself into it. This is kind of one of the big things we talk about. Thinking of our client who got to us so quickly, got back to us so quickly and was already interested in help getting another job. Yes.
Caanan (14:37)
Going to the next level
Kent (14:38)
It's like, okay, you've got to honor, you've got to figure out how you feel about the now.
Kent (14:44)
Yeah. And yeah, we this is this is one of our biggest why are we still doing that?
Caanan (14:50)
Yeah, and take time to be present for the thing that going back to what we were talking about in the first segment, you believed at the time you booked for this story, the Cinque Terre that this was going to be a fulfilling moment for you. Otherwise you wouldn't have done it. And then you get to the Cinque Terre in the case of this woman, and you're not even there, which I find so
Caanan (15:19)
Tragic. But to another thing you said, I think one of the big problems here is this is a lot of social conditioning. Yes. And there's a great deal of social currency in what's next. There's not a lot of social currency in what is right now. Yeah. And you brought up the stock market or, you know, investor returns and this is very much coded into our everyday lives with the stock market with
Caanan (15:48)
Consumerism would late stage capitalism. With
Kent (15:50)
yeah.
Caanan (15:51)
social media, we're steeped in what's next.
Kent (15:55)
Yeah, we don't blame you. We blame the culture and society, but we expect you, and this is what we work with people on, we expect you to start to see that in order to build a more fulfilled life for you, the people you love, and to hopefully keep working towards a no-vocation required existence.
Caanan (16:16)
Yes, 'cause I said there was social currency in what's next, but you know what there's a lot of social currency in, like the new social currency being present, yeah, being deeply fulfilled, not being part of this insane game we've all been playing and many of us are continuing to play, despite knowing that it never returns. It never gets fulfilling.
Caanan (16:45)
If you're always looking for fulfillment in what's next, if you're always looking for fulfillment in something outside of yourself. So, you know, the new hot thing is being fulfilled by focusing on knowing yourself and being in the present moment.
Kent (17:05)
Yeah. And Caanan and you said something just before we started recording. You were talking about so many of the posts and the podcasts we've done lately about the fraught world in which we all find ourselves. Yeah. And we need more people with this energy. Yeah. Calm, invested, present. Yes.
Caanan (17:29)
Present.
Caanan (17:31)
Happy in the moment. Yes. You want to be the person that people want to be around. Be that person. It's good for you. It's good for all the people you're around. And there's some real social currency because people are struggling to achieve this level of fulfillment. And we're all craving it, all longing for it. It's why we're all so focused on what's next.
Kent (17:53)
Reminds me of a post in an episode we did a while back. It's like, be the person that you want to be around. Like, who are you surrounding yourself with? Number one. And how am I contributing to that vibe? And I think when you start to unpack, like, wow, maybe I should be the person that other people actually want to be around. And I can determine what that is by asking myself the kind of people I want to be around. And those people are people that
Kent (18:23)
are engaged in whatever version of you shows up and the now and the thing you just did, even though it's not the hot new thing you're gonna do next.
Caanan (18:45)
I wanna kick this segment off by reading this quote or quoting the post that we wrote because I think this is a great kickoff for some tips on how to get out of this what's next cycle. Yes. So yeah, in the post we said that's why chasing the next level rarely brings real satisfaction. You reach the summit, snap a quick selfie, and immediately start looking around for a better view.
Caanan (19:15)
That's because you weren't climbing for the experience, you were climbing for the validation. Validation is external and fleeting. It doesn't settle in, it doesn't ground you, and it certainly doesn't last.
Kent (19:29)
Yeah. So this brings us right back to our core toolkit, our number one, which is know yourself. People who tend to be distracted in this kind of noise and chaos have a high overlap rate with people who don't really know themselves. This has nothing to do with education or job or wealth.
Kent (19:58)
It's just this hum of distraction that lives in your brain. I think of a good friend we were talking with recently and she said, I I can't even get on social media anymore because my FOMO brain is buzzing constantly. And she said, The minute I open social media and see the this and the that and the trip and the perfect outfit and the dream relationship, it does not
Kent (20:27)
make her want to get over it. It she said literally sends her spiraling. Yeah. And she's working on some really great techniques to get grounded in who she is and what she wants. And that is our number one advice. When you know who you are and what matters to you, that dissonance, that fakery becomes more apparent.
Kent (20:55)
Because there's part of your brain that's asking, wait, why are you acting like you care about this? Or why are you pursuing this? Why are you participating in this? Yeah. It does not align. So you're going to be more likely to say something, to bring back the interaction, or to bring back your own mind or your own ambitions to a more grounded, authentic place with what you're made of
Kent (21:24)
and what you truly want as the framework from which you work. So in order to remove this clutter, we say do work to figure out
Caanan (21:36)
You. I want to lean into that because it's incredibly important advice. And it's the only way out of this situation, this FOMO, longing, exhausting, what's next, seeking external fulfillment is knowing yourself. Because what you just said, if you know yourself, then you can explore the cravings that come up. And you can't...
Caanan (22:04)
For the most part, you can't not have these cravings. We live in a society that is built to make you crave things. So there's no shame in having the cravings or having the thought, I want to do that, or I want that outfit, or I want to go to that place, whatever. Our entire society is built to make you do that. But if you know yourself, you can do the important step of saying, Why am I thinking that? Yeah.
Caanan (22:34)
Do I want that? Is that important to me? Does that matter to me? Yeah. Would that feel fulfilling?
Kent (22:40)
And let me jump in here and say, because you know yourself, our tip number one, when you ask that question, you have a foundation for an answer. If you don't know yourself, you avoid that question because that question then just sounds like part of the noise and part of that distraction that our friend speaks of wanting to avoid because you don't have a way to calm that voice down.
Kent (23:07)
But if you know what you're grounded in, and when we say know yourself, we speak predominantly of your strengths, your values, your personality type, what you're meant to be doing, so to speak, then this question Caanan is speaking of becomes something that you can actually address from a place of confidence and move toward then behaving and speaking in a way that aligns with that.
Caanan (23:35)
Perfectly said. Yeah. And then once you've done that and you're actually able to answer the question, do I really want this? Does this really matter to me? You can answer that confidently because you know yourself. Then you can start doing the next thing, which is creating fulfilling moments in your life where you are based on who you are. And we're not talking big moments. Yeah. We hope you go to the Cinque Terre if you've not been, it's
Caanan (24:04)
Lovely. Lovely, lovely, lovely. You should go. But
Kent (24:07)
And you should go to Madonna's party if you're ever invited.
Caanan (24:10)
You're ever invited to Madonna's party, do go. But as we say in the post, don't go expecting that that's going to be fulfilling, because very likely once you get into Madonna's party as Neil Patrick Harris experienced, there'll be another level that is built to make you feel like you haven't reached the end yet. Yeah. what I'm saying is be once you know yourself, you can ask the question, will something be fulfilling? Does something matter to me?
Caanan (24:39)
And after you answer that, you can start creating moments in your life right where you are. I'm gonna say it again, right where you are. Yeah. That bring the fulfillment you're longing for.
Kent (24:50)
Yeah, and I wanna I wanna this is like a big spoiler alert. I wanna talk about what is this, the paradox of fulfillment or the paradox of craving. Once you practice this, and we've seen it in ourselves, our closest friends, our clients, once you've practiced this enough, you're not then ordering your thinking about where you wanna travel to next or your next bucket list item or the next grand
Kent (25:19)
Meal you want to make or whatever, you're realizing like, wow, my deepest fulfillment comes from mostly the smallest, most intimate, focused things in my life. The fifteen extra minutes spent lingering over coffee
Kent (25:50)
and rounding out your journaling moment or your brainstorming moment, the ten extra minutes spent sitting in the sun in the park, the beach. It leads you right to those tiny things. And then all of this noise that you thought you were separating out, you realize is oftentimes
Kent (26:19)
Centered in fun and exciting and bucket list things, but that that whole realm is not where you're finding your true what resonance, yes, pace and and cadence. That in fact, when you say, Why are we still doing that? Why am I still grasping at external things and participating in FOMO, when you ask that
Kent (26:49)
you're gonna find that it's the tiniest things that light you up the most.
Caanan (26:58)
That's exactly right. And I think I know what you'll find is as you get to know yourself, you will, like us, find that what you really crave in life are very simple things. Yes. And they're things that you're probably quite rich in right now. Yeah. If you just allow yourself to notice them and lean into them and let
Caanan (27:27)
let them be the things that fulfill you.