Aleksandar Blazhev

Are you a planner or do you go with the flow?

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There are two types of people (more or less):

1/ The ultra-planners. Тhey schedule everything down to the minute, know who they’re meeting three months from now, and already have their 2027 summer vacation mapped out.

2/ And then there are the freestylers. Тhey don’t know what they’re doing two hours from now, let alone next week.

Which one are you?

Personally, I’m somewhere in between.

I like planning ahead for some things. It gives me routine and mental space. But for others, I leave it completely open.

Case in point: I have no clue where or when I’ll take a vacation this summer. I know it’ll be in September and I want it to be by the sea, but that’s about it. I’ll figure it out later.

Curious where you land on the spectrum: planner, improviser, or a mix of both?👇

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Holden Lewis
I’m definitely more of a freestyler. I like the idea of planning, but honestly, I rarely have the time or mental bandwidth to map things out like an “ultra-planner.” That’s actually why I’ve been really interested in the potential of tools like Aster, which we’re building specifically for people who see the value in planning but don’t want to spend hours doing it. It’s more about light structure than rigid scheduling: quick, digestible plans that help you feel organized without overhauling how you naturally operate. Feels like there’s a big middle ground between hyper-planners and complete improvisers, and I’m firmly in that space.
Adi Singh

@cholden_lewis I agree, what are you launching?

Holden Lewis
@adi_singh5 Asterapp.ai ! It’s a multi-LLM AI planning agent and assistant. Focused more on helping people plan around daily life, meals and events/trips as opposed to work. Check out our site and if you want to try the beta let me know or fill out the form on our site! Would love feedback from people on PH.
Adi Singh

@cholden_lewis Did it! Looks sick man! excited for your launch

Aleksandar Blazhev

@cholden_lewis why you prefer freestyle?

Holden Lewis
@byalexai it’s less of a preference and more just who I am. Good to have a plan, but also good to be ready for when things don’t go to plan! Gotta play it fast and loose sometimes.
Zagita

Haha, I feel this! I’m 80% freestyler—terrible at detailed plans (even though I’m weirdly meticulous at work). When I do make plans, they’re rough sketches because if I commit? Oh, I’ll obsessively stick to them. Zero flexibility mode activated—can’t handle disappointing myself or others! 😅

Btw, for your September seaside vacay: Bali or Lombok would be perfect! Gorgeous beaches, great food, and (aside from flights) surprisingly budget-friendly. Just avoid the ultra-touristy spots if you want peace.

Adi Singh

@rani_zagita Great tips!!

Nika

Honestly, I would rather strategically plan with some schedule (but it is sometimes limiting) so I am trying to be less anxious when things need to be fixed along the way :D

Aleksandar Blazhev

@busmark_w_nika How far in advance do you plan your schedule?

Nika

@byalexai It depends on what activity to plan. But generally, plan quarterly. 3 months.

Kerem Can

I go in with a plan. I map out every section, estimate the time, try to be organized. Then I start working... everything falls apart, and I freestyle the rest.

Aleksandar Blazhev

@keremcan01 what's your plan for the next week?

Kerem Can

@byalexai testing out yt shorts to find users for our product, and working on a new newsletter we are launching. All this asides usual networking on x, reddit, linkedin, etc. Busy lol.

Betsy

I do a bit of both. I usually plan only the previous day instead of the whole week, which gives me better visibility into what I actually got done and what needs to be carried over (if any). That way, I can plan the next day more realistically.

Planning every single day of the week in advance (except repetitive everyday tasks) used to overwhelm me, especially if something unexpected came up or a task took longer than expected.

When it comes to regular tasks, I don’t assign rigid time blocks for each one. Instead, I set an overall time estimate for the group, just enough to give me a clear sense of how much time I should spend if I want to get through everything I’ve planned, but without stressing myself out with overly strict scheduling.

I also block out mandatory buffer time each day. If there’s extra work, I use it, and if not, I don’t treat it as relaxation time. Instead, I treat it as extra time (apart from allotted time) to read more about industry trends or tune into current conversations.

And of course, I set aside time for personal life and proper “me time” that’s honestly helped me stay way more productive than an always-on work mode.

And as for your Vacay, Andaman is serene, nature-heavy, and it's basically sea all around. Perfect to unplug, if that’s what you’re aiming for.

Aleksandar Blazhev

@betsykittu You're being really smart about it. I always get frustrated when I can’t finish my entire to-do list, but the truth is . It’s impossible to get it all done, especially considering I put 1,000 tasks on it.

Betsy

@byalexai "especially considering I put 1,000 tasks on it." haha I feel that in my bones. I was like that, then kinda experimented with routines till I found this.

Aleksandar Blazhev

@betsykittu maybe you cracked the code

Tom Ideaxton

It depends on the situation. But I try to plan ahead. Think through every action. Sometimes improvisation can backfire.

It's probably much easier to follow a plan.

Adi Singh

I like that Tom!

Robert Nelson

Freestyle unless my partner is involved and then it’s plan the hell out of everything! 😂

Aleksandar Blazhev

@robert_nelson8 why? he loves to make a plan?

Dheeraj

It's weird, I live somewhere in between. I know who I’m meeting three months from now. I’ve got the broad strokes of my quarter mapped out, and I tend to make long-term decisions pretty early - travel, projects, major commitments. Those things give me structure and vague narrative.

But when it comes to the day-to-day, I don’t use time blocks. I don’t tell myself I have to do Task A at 10:00am sharp. It's too stifling. Instead, I break my work down into pieces and assign them to days. I know what needs to be done, and I make sure each day has its role. But I don’t let time control the process. I try to work fluidly.

Some of my best work has happened outside “productive” hours: late at night, on a walk, or in those strange in-between pockets of time that schedules usually overlook. So I plan the big picture, but I leave room. This balance works best for me.

Aleksandar Blazhev

@dheerajdotexe tell me your plan for the next 3 weeks

Randeep Wilkhu

Definitely a planner. My calendar’s stacked, my to-do lists have to-do lists, and I get weirdly excited about scheduling things in advance. I do leave a bit of room for last-minute stuff, but honestly, I’m way more relaxed when things are mapped out.

Mirabelle Morah

I'm both. Can't plan too much and won't freestyle beyond a certain threshold. I like the wiggle room and structure and I'm balanced.

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