The B2B Podcast Index
Wantrepreneur to Entrepreneur

1499: NO ONE tells us what to do in this in between period...

Wantrepreneur to Entrepreneur · 2026-06-26 · 17 min

Substance score

14 / 100

Five dimensions, 20 points each

Insight Density4 / 20
Originality3 / 20
Guest Caliber2 / 20
Specificity & Evidence2 / 20
Conversational Craft3 / 20

Brian Lo Fomento explores the often-overlooked transition periods between entrepreneurial seasons, arguing that the uncertainty between seasons is harder than the seasons themselves and requires a fundamentally different mindset. He uses the metaphor of caterpillar-to-butterfly transformation to explain why entrepreneurs struggle during these "in between" phases where old identities no longer fit but new ones haven't yet formed. The episode frames transition uncertainty not as a warning sign but as evidence of growth and transformation.

Key takeaways

  • Transitions between seasons are harder than the seasons themselves because they remove the clarity and certainty that each season provides, requiring trust and faith instead of confidence.
  • Most entrepreneurial problems are identity problems rather than operational ones - you must reinvent yourself across different seasons, but your self-image typically lags behind your actual circumstances.
  • Uncertainty during transitions is often a growth signal, not a failure signal; the discomfort of transformation is the point, not a sign you're doing something wrong.
  • Transitions only make sense in reverse - you cannot connect the dots or understand their purpose while in them, only when looking back at them.
  • The purpose of transition periods is transformation itself, not clarity; rushing through them to find answers defeats the actual work that happens between seasons.

Topics in this episode

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

4 / 20

The episode is a 17-minute motivational monologue that generates almost no actionable insight for a B2B operator. The bulk of the runtime is filler, repetition, and generic encouragement dressed in seasonal metaphor. The one semi-interesting claim - that most entrepreneurial problems are identity rather than operational - is stated but never unpacked with evidence or mechanism.

I'm increasingly convinced that let's call it 90%. I'm comfortable going there. Uh, I want to say 80, because the 8020 rule is generally true in entrepreneurship. I'm gonna say 90% of the problems that we face are identity problems.
transitions offer precisely zero of those things. They require trust, they require faith.

Originality

3 / 20

Every idea here - seasonal metaphors, the chrysalis transformation, imposter syndrome during transitions, connecting dots only in reverse - is well-worn self-help content that circulates constantly in entrepreneurship podcasting. There are no contrarian or first-principles arguments, and the 'dots connect in reverse' framing is a well-known Steve Jobs-adjacent idea recycled without attribution or fresh angle.

Uncertainty is often the evidence that something is changing.
The finish line that we so often imagine becomes the starting line for something else.

Guest Caliber

2 / 20

This is a solo host monologue with no guest whatsoever. The host's only stated practitioner credential is ten months of corporate employment after college before becoming a podcast host. There is no operator, founder, or executive with demonstrated scale sharing hard-won knowledge.

I did work a corporate job for 10 months right when I graduated from college. And I'll never forget the day, the last day that I walked out of that office.
almost 20 years of being an entrepreneur and almost 1500 episodes behind the microphone

Specificity & Evidence

2 / 20

The episode contains virtually zero specific data, named companies, real metrics, or concrete timelines relevant to B2B operators. The only numbers present are the host's ten months in a corporate job and the episode count milestone. Everything else is abstract metaphor and assertion.

I did work a corporate job for 10 months right when I graduated from college
episode 1500 is, yes, a little bit of a milestone

Conversational Craft

3 / 20

As a solo monologue there is no interviewing craft, no follow-up questions, and no productive disagreement. The rhetorical questions posed are entirely self-answering and function as transitions rather than genuine inquiry. The host's self-interruptions and filler phrases ('uh', 'I mean', 'excuse me') further undercut the craft.

What if this isn't a clarity season? What if this is a transition season? What if uncertainty isn't the problem? What if uncertainty is the assignment?
Make sure you pound that subscribe button because we'll see you, as always, every single day right here on the wantrepreneur to Entrepreneur podcast.

Conversation analysis

Computed from the transcript - who did the talking, and the verbal tics along the way.

Filler words

so24uh11you know10like9actually4right4um1kind of1anyway1

Episode notes

After a full week exploring the four entrepreneurial seasons - Planting, Growth, Pruning, and Harvest - Brian is pulling back the curtain on the most challenging, misunderstood, and crucial phase of them all: the transition. It's the messy, uncertain space between the seasons where the old rules no longer work, but the new ones haven't revealed themselves yet. In this reflective solo episode, Brian argues that this "in-between" period, which often feels like failure or imposter syndrome, is actually where your most profound transformation occurs. Get ready to reframe uncertainty not as a problem to be solved, but as the assignment you’ve been given to prepare you for what’s next. Why This Matters for You Understanding the transition phase is critical for your sanity and success: It reframes uncertainty from a warning sign into a growth sign, helping you navigate those moments when you feel lost. It normalizes the feeling of being "in-between" - no longer who you were, but not yet who you're becoming. It helps you embrace the necessary identity shifts that entrepreneurship demands at every level.

Full transcript

17 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Hey, what is up? Welcome to this episode of the Wantrepreneur to Entrepreneur podcast. As always, I'm, um, your host, Brian Lo Fomento. And with episode 1500 right around the corner, this has been a very special week here on the show because this week I am feeling a little bit nostalgic and certainly a lot. Bit reflective. And that's why we are talking all about entrepreneurial seasons. And these seasons don't just come and go like the weather. These seasons sometimes last a long time. Sometimes we cycle through seasons all in the span of the same week or sometimes even the same day. But my big argument here in this week about entrepreneurial seasons is that every season demands something differently from us, and every season looks to reward us with different gifts that we can take into future seasons with us. Uh, so these seasons are important. I'm excited about this one. Let's dive in. So if you've been following along with this week's content in this miniseries about entrepreneurial seasons seasons, then you already know all four seasons that we talked about this week. We started the week off by talking about planting season and why sometimes it doesn't feel like things are happening, but the very important ask questions that we need to ask during that season and importantly, the very actions that we need to take during planting season. Then once you plant a seed, what do you hope happens to that seed? You hope that it grows. And we all think that growth is the goal. But in growth season, in that episode, we talked about how growth doesn't necessarily feel good all the time, and it can be a little bit counterintuitive. And that's why we have that phrase in English of growing pains, because there are pains that come along the way. So it's important for all of us to be able to recognize those, to lean into them, to understand what is coming our way. And then in the third episode this week, we talked all about pruning season, which is not the season that everybody wants to be in. Uh, addition by subtraction isn't always our favorite thing to talk about, but pruning season plays a very important role in our growth. So if you missed that episode, definitely check out the pruning season episode. And then yesterday's episode was the one that most people enjoy, but it definitely came with some big cautions, which is harvest season. This is the season that we think is the goal, when the truth is, is that if you think that you just get to enjoy your harvest, then nothing's ever going to grow again. Which is why all of These season are cyclical. They are all essential. They are all the goal because one builds upon another, one feeds from the last. They are such important seasons to understand because our behavior needs to be different in each of them. Our decisions need to be different in each season. Our questions need to be different in each season. And so today's episode, now that we've covered all four seasons, which I definitely invite, you go back, make sure you are able to identify those seasons, and you know how to handle each of those seasons. But today I'm going to talk about something that almost nobody understands about seasons. Because seasons are very easy to see when they're already here. Most people think that the hard part is the season itself, because each season does have challenges. Planting is hard, Growth is hard. Pruning is maybe harder for a lot of people, Harvesting, believe it or not, is also hard. I've come to believe that the hardest part of all of these seasons, uh, though, is actually not the season itself. It's the transition between them. Because seasons at least give you clarity. And hopefully after this week's episodes, they give you even more clarity when you have this awareness, when you know what to expect, when you know how to get through each of these seasons. But transitions between seasons give you uncertainty. And take this from a native New Englander having grown up in the Boston area, I know full well that nature does not announce the change of seasons or one day it is winter, one day it's spring. It doesn't mean that you've gone from one season to the next. There is not a giant sign that appears saying, congratulations, you are now entering spring. Not only does the transition happen gradually, but sometimes the transition feels completely murky where you are convinced, hey, we're out of winter. And then the next day you are convinced, oh, my gosh, wait. We're actually definitely still in winter. This stuff happens almost invisibly. Life works the exact same way. We've all experienced this in our lives and entrepreneurship. Of course, it's a microcosm for life. It also works the same way, the major transitions that we get in our business. You hear us talk a lot on this show about inflection points. They don't announce themselves. We only recognize them in hindsight. And it's something I'm very cognizant of as a podcast host when I have these conversations with amazing founders, that this stuff sounds linear. It sounds like it makes sense in the moment. It sounds like we always knew what to do. Only in hindsight. So much easier for myself and for guests on this show to talk about our journeys in hindsight, when all the dots are connected. But we've got to talk about the uncomfortable place to be. And that place is the transition point where you're no longer who you were, but you're also not yet who you're becoming. That's the transition. And entrepreneurs, we spend way more time there than we probably realize. Think about it. The day that, uh, I don't know what your work situation is, but I did work a corporate job for 10 months right when I graduated from college. And I'll never forget the day, the last day that I walked out of that office. When I left that office, I was no longer an employee, but I wasn't exactly yet, uh, a business owner. It was that really weird in between phase, or when you hire your first employee, you're no longer doing everything yourself, but you're also not a true leader just yet. There's that in between period where you don't exactly know what you're doing with that new hire. When you launch a podcast, you're no longer just a listener. Like, that's it. Uh, everybody who I talk to who listens to podcasts, they always say, oh, yeah, I love podcasts. I love being a podcast listener. Well, when you launch your podcast, you're no longer just a listener, but you're also not yet a podcaster with an audience. There's that in between phase where you feel like a fraud. We all experience that. That's where imposter syndrome is definitely at its roughest. And that's why those in between periods, they can often feel like failure, but they're not. They're the transition. And that's why I wanted to close this week by talking so much about this transition, because that's where a lot of our time in this journey goes towards. And transitions don't always feel great. In fact, most often they feel bad because transitions remove certainty. During planting season, you know exactly what to do. Plant those seeds, start those conversations. Say yes to everything. During growth season, you know what's happening. You can focus on that growth. Those things start appearing in front of you because of the seeds that you've already planted. During pruning season, at least you know what you should be doing. Removing, starting to say no a little bit. During harvest season, you know what you're seeing. You're finally seeing that evidence. You're fine. Excuse me, you're finally seeing those results. But between seasons, nothing is obvious. The old rules don't work anymore because you're no longer in that Season of business or in life or in that journey. But the new rules haven't revealed themselves just yet. And that's unsettling. And when I think about how many things in life and in nature, this transition kind of doesn't make as much sense. I think so frequently about caterpillars. Uh, if you know me personally, you know that the number one least favorite thing that I have in life is pests. If there's a single pest in my house, it drives me up the wall. I am certainly not a bug person. And so I just. I shake my head when I see how many people, they love caterpillars and everybody loves butterflies. I do not join in that camp. To me, again, just a pest. I don't want bugs anywhere near me. But we're so familiar with those two. But nobody talks about that. In between phase, the messy middle, the transformation. We don't necessarily see that societally. We see caterpillars, we see butterflies. We don't see that in between. Actually, I had to Google, what is the name for the in between being a caterpillar and becoming a butterfly? There's a scientific name for it, the chrysalis. I have no idea how to pronounce that word, but I did look it up. I've never even heard that word. And that's the entire point, is that that messy middle, the transformation, the stage where neither identity fully exists, that's where the change is happening. But we don't even talk about that. We don't even see it. I didn't even know what it was called. Maybe you did. If you're screaming chrysalis at your headphones right now, then huge kudos to you for paying way more attention in science class than I did. Entrepreneurs, we often want those butterfly results without embracing or stepping into or desiring the chrysalis season. And so the identity gap is real in entrepreneurship of being a caterpillar, becoming a butterfly, but being in that in between phase. And that's where. How frequently do we talk about. Most entrepreneurial problems are not operational, they're identity problems. It's why from the very first day of this show launching, we've always had mindset and motivation episodes. I'm increasingly convinced that let's call it 90%. I'm comfortable going there. Uh, I want to say 80, because the 8020 rule is generally true in entrepreneurship. I'm gonna say 90% of the problems that we face are identity problems. Think about how often along this journey we have to reinvent ourselves. We don't have to reinvent our businesses all the time. But we do need to reinvent ourselves because we start as a beginner. Maybe we're a builder at times, maybe we're a creator, maybe we're a salesperson, maybe we're a leader, maybe we're an operator. And that's what we talk about in pretty much every conversation. It comes up all the different hats that we all have to wear. And the reason is, is because there's not a single hat that once we find that hat, we go, wow, this fits. This is exactly what I need to wear. Different seasons require different versions of you. And the challenge is that identity often lags behind reality. Your circumstances actually end up changing before your self image does. And so it's this never ending game of leapfrog where we have to catch up to where we are. Which is why of course, I feel like self reflection and awareness and knowing these stages is so important in these seasons. And that's why we have dedicated this entire week to it. Because as episode 1500 comes up, I feel that own transition as well. Behind the scenes at this show and this show, if you've been following us for a long time, you also know how much this show has evolved over times. And so episode 1500 I'm very excited about. We're going to have some amazing content resources. We are up leveling in some very meaningful ways here in the second half of 2026 and beyond. Because milestones always give us an opportunity to ask a very important and interesting question, which is now what? Now what? The reflection or, uh, the milestone is never the finish line. The finish line that we think, you know, reaching. Oh, episode 1500, I don't know where this ends. I have no idea where this podcast ends. Are we gonna hit episode 10,000 one day? I have no idea how crazy would that be. But the finish line that we so often imagine becomes the starting line for something else. And when that happens, guess what? We're not in a season again. We're in between seasons. We are in that transition. And most people, it's very easy to interpret transition as failure because those are the moments. These are the creepy moments that sneak up on us where we feel that uncertainty and we think, naturally, I must be doing something wrong. Something needs to change. I need to overhaul things, I need to pivot, I need to quit. I need to do this instead. No. Uncertainty is often the evidence that something is changing. Think about that caterpillar. They probably have no idea what on earth they are going through. I cannot imagine what that must be. Like, for them. And it's probably very uncertain, it's probably very uncomfortable. Little do they realize that they're about to become a butterfly. So the discomfort isn't necessarily a warning sign. Sometimes it's a growth sign, a transition sign, a transformation sign. And in a world where we, as humans and as entrepreneurs, we love clarity, we crave clarity, we hope for clarity, we want the roadmap, we want the blueprint, we want the certainty and the guarantees. Transitions offer precisely zero of those things. They require trust, they require faith. No confidence at that stage. I think we can all relate to the fact that there is no feeling of confidence or certainty there. Confidence, if we could have it, says, I know what's going to happen. Whereas trust and faith invite us to step into this very powerful and once you can accept it, peaceful notion of, I have no idea what's gonna happen, but I'm gonna keep moving forward anyway. And those are very different things. And I think the thing that I'm most cognizant of as a podcast host is that notion of the strange thing about transitions is they only make sense in reverse. You can only connect the dots when you look backwards, never, ever forwards. Gosh, if I look back at my journey, the one thing that I do hold near and dear to me is the memories of, what was I feeling in that moment? What was I thinking? What was I optimistic about? What was I hoping for? What did I convince myself of? And most of the defining transitions in my life probably felt confusing in those moments. Only now, when I talk about them in reverse, do they feel obvious. Well, of course that was gonna lead to that. And so every episode this week, uh, I've led us to a question, a question that I think we should be asking in these periods and in these seasons. And so when it comes to the in between seasons, there's also a question we don't ask. Why don't I have clarity? We ask, what if this isn't a clarity season? What if this is a transition season? What if uncertainty isn't the problem? What if uncertainty is the assignment? Because that uncertainty invites us, forces us to ask questions every season that you've heard from this week. If you're thinking, oh, uh, man, I love planting season, I love growth season, or maybe, hey, pruning season. I've never done that. That's fun to step into. It's a really fun challenge, or, hey, I really want to get to harvest season. You always have to remember, this is the key thing about seasons, is that every season eventually ends. Planting ends Growth ends, pruning ends, harvesting ends. And when they do, we're invited into a place that most of us resist. The in between, the transition, which is what today's episode about the uncomfortable space where the old version of our life no longer fits and the new version has not yet fully arrived. It's tempting to wanna rush through that space to demand answers, to demand certainty, to demand clarity. But maybe the purpose of transition is not clarity. Maybe the purpose of transition is that transformation. And if there's one thing I've Learned over almost 20 years of being an entrepreneur and almost 1500 episodes behind the microphone, it's that you do not become someone new when the next season arrives. You become someone new in the space between them. So here's to a really fun week here on the show. I hope that its moments have hit you where you needed them, when you needed them, how you needed them. Because these are the real seasons that we all go through that we all can relate to each other on. And of course, in today's episode, it's all about those in betweens which we all spend a lot of time in. So hopefully this has been helpful. I'm so grateful for you being here for however many episodes you tune into, for however long you have been tuning into this show. Episode 1500 is, yes, a little bit of a milestone, but it's also a little bit of a transition because milestones invite us to dream bigger, to think bigger, to ask new questions. So I'm so excited about all the stuff that we've got coming your way in the second half of this year and beyond. So make sure you pound that subscribe button because we'll see you, as always, every single day right here on the wantrepreneur to Entrepreneur podcast.

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