How To Estimate Your Time When Starting Something New

Alexis Haselberger
4 min readJun 3, 2024


Image created using ChatGPT

I want to tell you about a time that something took WAY longer than I anticipated, and how I handled it. Why? Because this type of thing happens all the time. To all of us.

Humans? Most of us just aren’t that great at estimating time.

And, even though I know this, and I have lots of practices in place to help me better estimate time, sometimes, things still go wildly awry.

So let me tell you the story of getting my podcast launched into the world.

Because this is a story of doing something I’d never done before.

And when you do something you’ve never done before, you’re typically even worse at estimating how long it’ll take. (Or, at least, I am.) Here’s what happened:

First, I laid out the phases because it’s MUCH easier to estimate time in smaller chunks than for an entire project, all at once.:

Then, I started executing the phases.

And I did a pretty good job (if I don’t say so myself!) of estimating how much time I’d need for most of the steps.

When I do something big I’ve never done before, I always take my best estimate, using the knowledge I do have, and knowledge of myself, and I multiply it by 3 to factor in the unknowns.

But then something happened that could’ve led to disaster.

During the “distribute” step, when I was SO CLOSE to the end, I ran into a snafu with Apple podcasts.

I’d already set up the distribution connections to a number of platforms, and it took about 10 minutes each, and then came the big one, Apple.

I was following the steps, but I just kept getting stuck in a hell loop. All roads led to “You haven’t fully activated your Apple ID”. But this was strange, as I’ve been using my Apple ID for years. What did it mean to activate it? How could it not be activated?

After about 30 minutes of this, when it was clear I wasn’t solving this on my own, I reached out to Apple for support.

I spent 2 hours (yes, 2 full hours!) on the phone with Apple support, I spoke to 4 people, while they “escalated” me.

No one could help.

These people were all kind, they all seemed knowledgeable. But, yet, none of them could figure out what was going on.

When the last one told me the only thing left was for me to submit a “complaint”, I was so frustrated I almost cried.

I had basically resigned myself to the idea that I was just going to have to launch without Apple Podcasts when, miraculously, one of the methods I’d already tried a million times finally worked.

And then I almost cried with joy.

So, in the end, something I’d expected to take 10 minutes, took, 3 hours.

And while there were a couple of small things I’d intended to do that day that didn’t get done, they all fell into the “nice to do” category, so I could reschedule them without much consequence.

AND, I’d built in buffer into my day specifically for this reason: to anticipate the unanticipated.

You don’t know what will come up, but something always does, and that’s why you’ll feel a whole lot better when you plan for it (even if you don’t know what “it” is yet).

Now, you might be thinking, “well, what would you have done if that thing had only taken 10 minutes, and you didn’t need all that buffer?”

Well, what a wonderful position to have been in that would have been!

Here’s what I would have done:

I would likely have done a few things that were scheduled for the next day on that day instead, ensuring that my week would go even more smoothly after that. (Or, if I was feeling tired maybe I would have even knocked off early.)

This is buffer.

This is Task Realism.

Things go wrong. Things take longer than you want them to.

And sometimes, it has nothing to do with you; the technology gods just aren’t on your side.

But it’s ok. You can pivot.

You don’t have to let it ruin the day, or the week.

You can plan for the inevitability of things not going your way.

As they say, “Hope for the best, but expect the worst.”

Happiness, and productivity, it seems, is all about expectations.

So, what’s the TL/DR for how to more accurately plan for something you’ve never done before?

  1. Break it down into phases/steps
  2. Estimate time for each phase/step
  3. Multiply your estimate by a multiplier that works for you (for me, 3x feels safe)
  4. Block the time you think you’ll need.
  5. Don’t beat yourself up for not being accurate; pivot as needed! You’re doing the best you can.

What can you do, right now, to set yourself up for success by building time into your schedule to account for the unexpected?

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Originally published at on June 3, 2024.