Vault: Bert Needs Time Management Advice

Summary

---

The Bert Show: Vault – Bert Needs Time Management Advice

January 29, 2026 | Pionaire Podcasting

Episode Overview

In this candid and relatable episode, Bert opens up to the Bert Show cast and their listeners about his struggles with time management. He invites advice from both his co-hosts and callers, discussing the broader challenges of balancing work, family, and personal fulfillment. The conversation dives deep into feelings of inadequacy, societal pressures, and practical strategies for reclaiming control over one’s time.

---

Key Discussion Points & Insights

1. Bert’s Struggle with Time Management

• Bert confides in the team about his perpetual difficulty in managing time, expressing that despite trying many routines, he still feels overwhelmed and like he's failing in all areas of his life.
  • “I just can't. I can't figure out time management to save my ass, okay?...I feel across the board right now, I am failing at everything in my life.” (Bert, 00:15)
• He describes his days as a series of rushed appointments (00:47), with nothing receiving quality attention.
• This impacts his work, his relationships—both familial and romantic—and his personal sense of effectiveness and purpose.

2. The Impact of Societal Expectations

• Katie observes that society undervalues free time and equates busyness with success, leading to exhaustion and feelings of inadequacy.
  • “Our society looks down upon any free time. If you're having free time or too much time on your hands, then you're obviously not doing enough.” (Katie, 02:16)

3. The Cycle of Stress and Not Feeling "Good Enough"

• Bert shares how this cycle erodes his self-confidence as a professional, father, and husband. He feels unable to maintain meaningful relationships with his family due to time constraints and constant demands (02:54 - 03:46).

4. Metaphor of the Undertow

• Jen likens Bert's experience to being stuck in an undertow: “It is just pulls you under and... you can't seem to get yourself back up. You just got to sort of halt everything, get your head out of the water and then reprioritize.” (Jen, 03:57)
• The undertow metaphor encapsulates that sense of being repeatedly pulled under by obligations, unable to break free without a reset.

5. Prioritization & Delegation Challenges

• Jen suggests delegating and learning to say no—prioritizing himself, though Bert feels “there’s no such thing as prioritizing,” since everyone else believes their requests are most important (04:24).
• Bert’s reluctance to let others down exacerbates the pileup of tasks and feelings of guilt.

6. Unrealistic Time Estimation

• Jeff points out Bert’s chronic underestimation of how long tasks actually take, which affects both Bert and those around him:
  • “You have an unreasonable expectation of time... You think ‘that's 15 minutes.’ In reality, it's 90.” (Jeff, 04:50)
• This creates a backlog of unfinished work and a persistent, discouraging sense of failure.

7. The Guilt of Modern Family Life

• Bert mentions a study about couples only connecting for “15 minutes before bedtime,” highlighting the challenge of meaningful family relationships amidst busy schedules:
  • “That’s the only connection time parents have... and it’s at the end of the day when it’s the crumbs of the day, you got nothing left.” (Bert, 07:32)

8. Practical Advice: Structuring the Day

• Jeff recommends writing out a schedule, blocking out time for each activity (including email), and sticking to it—even if not everything gets done. (08:00)
  • “You write that down ahead of time...and you get to what you can get to.”
• If emails or tasks remain unfinished, it’s okay to leave them for later and communicate, “I’m sorry, I didn’t have time.” (08:42)

9. Mindfully Focusing on One Thing at a Time

• Caller Anna (09:17) and others highlight the importance of setting clear expectations for meetings and focusing wholly on the present task:
  • “You say, okay, I have this half an hour for the meeting, and you set the expectation at the beginning... and you let everything else go for that next half hour.” (Anna, 09:19)
• If more time is needed, explicitly schedule a follow-up rather than running over.

10. The Power of Saying No

• Another caller, Anna (11:24), emphasizes learning to say no and “internalizing it.”
  • “My best advice to you is to learn how to say no. Yeah, you have got to be able to do that and internalize it and be in the moment.”
• Jen and Katie reinforce that managing others’ expectations and not attending every meeting frees up time for deeper work and personal well-being. (11:35)

11. Scheduling Personal Time

• Katie and Jeff advocate for blocking out personal time as diligently as professional commitments:
  • “You should also get into the habit of filling in those meetings with yourself... there's no reason why you can't schedule something for yourself in that time and say, 'yeah, you know what? I've already got something. I've got an appointment at that time.’” (Katie, 13:23)
  • “For my schedule from 11am to usually 8pm is personal time. I block it out. So if somebody asks for me during that time, I'm like, no, I'm in a meeting, but it's a meeting with myself.” (Jeff, 13:58)

---

Notable Quotes & Memorable Moments

• Bert, on the weight of unmet demands:
  “Everybody has to be number one. And if they're not, they're coming down on you.” (Bert, 04:45)

• Jeff, on time misperception:
  “You stack up six 15 minute projects... By the time you get done with your email that you thought was going to take two hours, the sun's setting.” (Jeff, 05:18)

• Jen, on the ocean wave of stress:
  “It's like sort of gets that ball rolling, you know, like that ocean wave that—” (Jen, 07:16)

• Callers’ advice on boundaries:
  “If business isn't done at 11:30, then what? Then it's an email.” (Bert & Anna, 09:44)

• Katie on family time in the past:
  “People who called our house after 6 o'clock...that was when they were home relaxing with their family.” (Katie, 10:21)

• Jeff, on blocking off personal time:
  “From 11am to usually 8pm is personal time. I block it out... I'm in a meeting, but it's a meeting with myself.” (Jeff, 13:58)

---

Important Timestamps

• 00:01–01:49: Bert opens up about his struggles with time management and feelings of inadequacy.
• 03:46–04:24: The undertow metaphor and Jen’s advice about stopping and reprioritizing.
• 04:50–05:49: Jeff discusses time estimation and project stacking.
• 07:32–08:00: The “15 minutes before bedtime” stat and discussion of intimate family time.
• 08:00–09:17: Jeff and Anna provide strategies for scheduling and sticking to boundaries.
• 11:24–13:09: Emphasis on the necessity and challenge of saying no and focusing on what matters most.
• 13:23–14:09: The concept of blocking out personal time as non-negotiable.

---

Conclusion

The Bert Show vividly details the universal struggle of modern time management. Through honest self-reflection, supportive co-host banter, and practical advice from listeners, the episode provides a toolkit for listeners seeking better control over their time and a reminder that the struggle is shared by many. The strategies offered range from strict scheduling to setting boundaries and learning to prioritize oneself without guilt, all delivered with The Bert Show's trademark warmth and humor.

Transcript

[Jeff Probst]

The bird show.

[Bert]

I want to keep it real with you guys here for a couple of minutes, and I'm actually asking for advice for you guys, okay? And I'm not even sure that anybody has figured it out, but if you have, please help me, because I can't.

[Katie]

Okay?

[Bert]

404.741Q100, y'.

[Jeff Probst]

All.

[Bert]

I just can't. I can't figure out time management to save my ass, okay? And this has been like, a reoccurring theme going on for me for who knows how long. And I think I feel like I have manipulated my schedule so many different ways that I should have been able to figure it out by now. And I just can't. I just can't. Like, I feel across the board right now, I am failing at everything in my life.

[Jen]

Just spread too thin. Or your just mind is always jumping from one task to the other, but not really ever accomplishing a whole project or.

[Bert]

Yeah. My day, it feels like, to me, is a series of appointments being rushed to. From one to the other, and never really giving too much attention to one thing. So everything's getting done, but it's just not getting done in a quality way. And it's so stressful throughout the entire day. Like, I don't really feel like I'm enjoying life. You know, like, we got meetings at 10:30. I kind of feel like I rush through those because I have a meeting with a salesperson at 11:15 or. And then at 11:15, getting to the gym at 2 is always on my mind. So I know that I only have a half an hour for that meeting. And then coming back home and doing show prep on the show, then to the gym, and then after the gym, there's more meetings or phone calls or whatever. It just always seems like I can't get caught up in anything. And it feels like I'm not good at anything anymore. Like, I don't feel like I'm good at this job anymore. I don't feel like I'm a good father. I. I don't feel like I'm a good husband right now. And I have zero idea, no idea how to break out of it.

[Katie]

I think that.

[Jen]

Contain it.

[Bert]

Yeah, I have no idea, y'. All. And usually when there's a problem, you know. Cause I'm a. I'm a pretty big proponent of just switch the routine a little bit. You gotta try different things if what you're currently trying isn't working. And I feel like it has been a lifelong mission to figure out different ways to manipulate my life in order for me to get some happiness out of it and for me to be able to work some time to where I'm enjoying the things that are going on around me. And I can't figure it out.

[Katie]

I do think that you probably get plenty of advice because I think most people feel that way because I do believe our society looks down upon any free time. If you're having free time or too much time on your hands, then you're obviously not doing enough. And I think that it's common when you feel, like Jen said, you're stretched then for you to feel like I'm not good at anything because you're not getting fulfillment out of things because you're just trying to check something off your to do list. And so, you know, it's not that it is true that you're not good at this job and that you're not a good father and not a good husband, but it's just if you're so worn down, then how else are you going to feel?

[Bert]

You know, it's not even. See to me it's not even a matter of time for myself. I mean, I just took a week where I was with myself. You know, as far as vacation goes, I got that covered. And when I'm on vacation, I am with the family or I am with myself. So I don't think that's the problem. The problem is the day to day. Like, I don't understand where is everybody finding the time? Like where are you guys finding time to have friendships? Where are you having? I can't think of the last time that somebody was happy with the relationship that I'm in. Like my mom is complaining now because I'm not in touch with her. My wife is demanding more time. My kids don't ask for the time. But I can certainly see when they're checking out and they're not as close to pop. You know, as I said with work, I just feel like I'm not completing everything that I'm not on top of, everything that I should be on top of. And I just feel like a failure across the board.

[Jen]

It's one of those things where it's like the waves are crashing over you now and you can't stop them. You know how like you can get caught in an undertow? Like the analogy of that. Have you ever been caught in an undertow?

[Bert]

I don't know.

[Jen]

I grew up in Florida, so I'm like a beach kid and that's like, you know, it is just pulls you under and Pulls you under and pulls you under and you can't seem to get yourself back up. You just got to sort of halt everything, get your head out of the water and then reprioritize, you know, because it sounds like to me, like maybe with the work stuff, there's like things that you could delegate and maybe things that you could just say, you start saying no to, you know, because there are some things you can, some things you can't, but you can't do it all, you know, you have to.

[Bert]

There's, I don't know, there's no such thing as prioritizing. It doesn't feel like to me, because everybody feels like the thing that they've asked you to do is the most important thing.

[Jen]

Of course.

[Bert]

So if, if they're ninth on your to do list and you don't get to it, the first thing you get the next morning is a complaint from somebody that you didn't get back to, an email from them from 24 hours before then.

[Jeff Probst]

Right.

[Bert]

Everybody has to be number one. And if they're not, they're coming down on you.

[Jen]

But you have to decide who's number one.

[Jeff Probst]

You have an unreasonable expectation of time. Like, you don't have. You have an unreasonable awareness of time. Like, I don't think you ever properly think of how long it takes to accomplish something. And I know you do it with like Tracy and I and interns and other people at the radio station. And I almost guarantee you do it to yourself.

[Bert]

You mean. So I'm looking at projects thinking it won't take nearly as much time as it does.

[Jeff Probst]

That's 15 minutes. In reality, it's 90.

[Bert]

Yeah.

[Jeff Probst]

So you stack up six 15 minute projects and you do it like, you do it to everybody around you. Like, Tracy's aware of it, I'm aware of it. Everyone in this building's aware of it. And I guarantee you do it to yourself. Where you think, you think, you know what? I'm going to answer my email. It's going to take me 30 minutes. Well, you know what? It takes two and a half hours because you got to respond back to people. So you think, all right, so I'm going to answer my email. It's going to take me 30 minutes. And I'm going to do this. Then I'm going to do this. Then I'm going to hang out with Hollis and Hayden and we're going to go sit in the backyard and have a picnic. Well, by the time you get done with your email that you thought was going to take Two hours, the sun setting.

[Bert]

Yeah.

[Jeff Probst]

And then you start to feel like you're a failure. Like you have to readjust, like your awareness of time.

[Bert]

So it's almost like.

[Jen]

Or how much you want to accomplish within certain amounts of time.

[Bert]

So if it's almost like, if it's realistically going to take an hour to answer emails.

[Jeff Probst]

Yes.

[Bert]

Should I just say after 20 minutes I'm done?

[Jeff Probst]

No, I think what you should do is you should decide if you're going to answer email. I don't know how to fix it because it's a weird thing. Like, I can better relate it to something that you would ask Tracy or I to do or you would ask somebody in the building to do. And I could go back through my email, but where you're like, hey, we should do this and this. And then because your classic response is, if we come back, know that that's. There's just no time. Like, what are you talking about? That's shooting off three emails and it takes 15 minutes. Well, it takes 15 minutes to find the contact person. It takes 10 minutes to write the email, then you have to shoot it off. Then they're gonna respond with 10 questions. Then you have to respond to that, which takes 30 minutes. Now, this might be spread out over two weeks, but in your mind it's a 10 minute project. Sure. Just shoot three emails off to Jeff Probst and have him come down and co host the show for a week. That's how it processes it, just an email. But the reality is the work that goes into finding the email address, tracking it down, and I guarantee you, you do that to yourself.

[Jen]

Oh, yeah. And then you're disappointed in yourself when it doesn't take you just 30 minutes to get through email. And you're 30 minutes in and you're like, I've only answered five of them. And so then you're disappointed in yourself. And then it's like, sort of like gets that ball rolling, you know, like that ocean wave that.

[Jeff Probst]

You know what, I think there's probably.

[Bert]

More to it than that. Also, like, I was just reading and I blogged about this, that the average parent spends 15 minutes with each other before bedtime. Fifteen minutes. That's the only connection time parents have with each other. And that's at the end of the day. And I'm really sensitive to this right now with Stacey. And it's at the end of the day when it's the crumbs of the day, you got nothing left.

[Jeff Probst]

Right.

[Bert]

And most people are getting 15 minutes a day. In their marriage to connect with their spouses.

[Jeff Probst]

You know what they tell people who work for themselves to do is. Which is kind of what you do. You know what I mean? This is a very independent job. We all work independently of an immediate supervisor, so we're all kind of working for ourselves. And they tell people who work for themselves to write out a schedule, and that's what you do. So you do the show until 10, and then you hang out till 10:30. You have your lunch till 10:30. Lunch break. Sounds weird to say lunch break at 10, but keep in mind our schedule. So we have a lunch break till 10:30. So our meeting is today, 10:30 to 11. And you, you write that down ahead of time. And then you say, okay, I've got 45 minutes to answer emails. And you get to what you can get to.

[Bert]

But then if you don't get to.

[Jeff Probst]

All of them, you don't have to. I'm sorry. You say, I'm sorry, I didn't have. I didn't have time. And you also, you're notorious for this too. You answer the emails. That can be answered quickly.

[Bert]

Yes, because my mind is already on the other project.

[Jeff Probst]

Right. But, like, you go through your emails, and if it takes.

[Bert]

You're guilty of that too, by the way.

[Jeff Probst]

Totally. And if that's how I know you are, because you go through your emails and you're like, I only have 45 minutes. And then you.

[Anna]

You.

[Jeff Probst]

You're like, hey, can you send me the ratings for spring of last year? I'm like, tomorrow I can click next and everything. And then it's like, what's your middle name? No problem.

[Bert]

Hey, Jada, you're on Q100. Good morning.

[Anna]

Hey. For me, it's a matter of mindset. It has a lot to do with what Jeff was just saying. You say, okay, I have this half an hour for the meeting, and you set the expectation at the beginning. I have to leave at 11:30. And then you are there for the next half hour, and you let everything else go for that next half hour because you know that's where you are and you know what you have next.

[Jen]

That's a good idea. It's like really focus in that half hour.

[Bert]

So you got a schedule. So you. And you let the people know, like right in the front end of your meeting. Look, we have till 11:30, and then that's it. Then you take off. So if business isn't done at 11:30, then what? Then it's an email.

[Anna]

Then you say. Then you say, at 11:25. You're like, we know this is going to take longer. Let's set up a time to follow up. Or we can follow up with email. I still have to be gone by 11:30. What are our next steps? I have.

[Jeff Probst]

Yeah, it's good.

[Jen]

Okay, that's really good.

[Jeff Probst]

It's really good.

[Jen]

That's really good. And it's really.

[Bert]

Sorry, Anna, you're gonna be the first one. I use that on there and it's.

[Jeff Probst]

Gonna be a practical call. It's gonna be a seven minute meeting. Two minutes into it. All right, guys, five minutes. I gotta go. Jeff told me to schedule emails from 11:15 to 12.

[Katie]

You know what, it's a different society now because I remember with my parents, like people who called our house after 6 o' clock in the evening, like it was weird for people to call us after dinner because it was known that that was when they were home relaxing with their family. So, you know, and I mentioned that to Katie not too long ago when people keep calling us at 8, 9, even 10. And it's like, you know what, it is odd for me because the way I grew up, it was after 6 o'.

[Jeff Probst]

Clock.

[Katie]

I mean, there had to be a special reason for somebody to call any of us because we were hanging out together.

[Jeff Probst]

If the phone rang in the evening, like while we were watching our show, somebody is dead, we would all look at each other like, who's calling?

[Bert]

Yeah.

[Katie]

And that's just not the case nowadays.

[Jeff Probst]

Obviously, until I became like a teenager and had friends and girls calling and stuff like that. But like before then, I remember sitting around at like 10 years old and the phone would ring and be like, everybody's panicking. What is that?

[Jen]

Somebody's dying.

[Jeff Probst]

Oh my God.

[Bert]

If somebody.

[Jeff Probst]

And if somebody knocked on the door after dark.

[Katie]

Oh, that was weird.

[Jeff Probst]

Like dad was loading a shotgun.

[Bert]

Hey, Fatty, you're on Q100. Good morning.

[Anna]

Good morning.

[Bert]

Good morning.

[Anna]

My best advice to you is to learn how to say no. Yeah, you have got to be able to do that and internalize it and be in the moment, just like they said.

[Jen]

It's so hard to do. And I think, Bert, you especially get pulled in a lot of different directions. But at the same time, I think it's managing other people's expectations of your time. You know, if someone says, I need you to come to, like, for example, like, I know what you're talking about going on, like behind the scenes, like, I want you to come to a brainstorming meeting about blah project. You can just say, listen, I can't be there. I'm sorry. No, I don't have time in the schedule. Let me know what you come up with. And so the other people have the. The responsibility for brainstorming and presenting you with, hey, we need two ideas. Here's eight. You want to pick two that work for you?

[Bert]

Okay, now that. That part would work for me. The only part I don't like about that is you got all these people coming up with ideas, and if they present them to me and I don't like them, then if I was on there, and I'd be like, we just spent three hours in a meeting coming up with these ideas.

[Jen]

And.

[Bert]

And he. It took him 60 seconds to shoot it down. Screw him.

[Katie]

But you're not a mind reader. You can't read their mind. You just do what's best for you.

[Jeff Probst]

But I don't think. I do think you have an obligation. If it affects you, that's a priority. Like, you go to that meeting. Like, the meeting that we're talking, the brainstorming meeting today. Like, you go to it, and you go to it for 45 minutes. And, you know, 30 minutes into it, you say, okay, we got to walk out of here with a couple ideas, because I'm leaving a fifth. I got to leave in 15 minutes. And I want to. I want to make sure we wrap this up for everybody who's in the room. You know what I mean? And you do it, and you just.

[Jen]

But I. I don't know. I do think that people have to be better prepared for, like, coming to the table to Burt with a blank slate and say, let's come up with some things I think is unrealistic. Like, I think people need to be, like, more prepared before coming into it.

[Bert]

And this is not just a me thing here. I think we're just talking about a time crunch with everybody. Like, everybody is stressed out about one thing or the other. You don't have to be the supervisor. You could be the employee. Everybody just seems like nobody has enough time to do the things that they really want to do.

[Jeff Probst]

Go ahead.

[Katie]

I think that you also. Everybody schedules meetings, and everybody schedules this, and they look at their calendars blank. They fill it in. Well, you should also get into the habit of filling in those meetings with yourself. Like, there's no reason why you can't schedule. You may tell somebody, look, I got a meeting, or, look, I don't have time on my schedule. Well, why can't that portion of your schedule be for you, be about you? Whether it be, you know, whatever it is that fulfills you at the moment, whether it be for 30 minutes or an hour. There's no reason you can't schedule something for yourself in that time and say, yeah, you know what? I've already got something. I've got an appointment at that time. But, you know, maybe we can reschedule for and make that appointment about you. Don't sell stuff out.

[Jeff Probst]

For my schedule from 11am to usually 8pm is personal time. I block it out. So if somebody asks for me during that time, I'm like, no, I'm in a meeting, but it's a meeting with myself.

[Bert]

I think I just might have got to the root of my problem.

[Jeff Probst]

The Burt Show.