I had just had a good run of projects, doing good work I was proud of in the right amount of time… and then, a couple weeks ago, disaster struck.
Here, let me tell you about it in this little video I made:
I had a string of projects to do. So, I did my best estimate on how long each project was going to take. For example:
- The Shareable Images Course will take about 3 weeks,
- Then planning the Small Business Roadmap podcasts will take about 2 weeks,
- And then this other project will take about 4 weeks…
I did a good amount of project planning, breaking up the steps, etc., to determine how long each would take.
Regardless, I messed up (pretty big) on how long the first project was going to take me, and it messed up our schedule, messed up my attitude, messed up our team plans, messed up my email inbox (because I wasn’t taking any time to maintain that while rushing on the late project), and ultimately spun me down into anxiety and depression.
All because I slipped up on how long I thought it would take me to finish a project.
The Planning Fallacy
So I looked into project time estimation, and, as it happens, I’m not the only one who has a hard time with it.
There’s actually a bunch of studies out there about, what researchers call, the Planning Fallacy. The gist is this: we are all over-optimistic about our time estimates.
“We chronically underestimate the time things take: that’s why Sydney Opera House opened 10 years later than scheduled, and why the new Wembley stadium opened last year, not in 2003, 2005 or 2006, each of which had been, at various points, the predicted completion date. It’s also why the list-makers among us get up each day and make to-do lists that by the same evening will seem laughable, even insane.” ∞
The Planning Fallacy, this over-optimism we have about plans, seems to effect all of us, regardless of culture or age. So, if you’ve ever been late on a project, you’re not alone.
But I don’t want to spend the rest of my life late on some deadline. If we can make more accurate estimates about how long something’s going to take, we’re going to spend more time doing GOOD work and less time doing stressed out crappy, rushed work.
So here are 5 tips to help you estimate how much time a project will take:
5 Time Estimation Tips
1. Double Your Estimation.
Now, this is kind of a band aid. A lot of the researchers poo poo this option, but it’s easy and quick and may help you a bunch right off the bat.
Simply make your best estimation for how long this project will take, and then double it.
If you estimate it’ll take you 3 hours to write a blog post, double that to 6.
You see, when we estimate we’re not foreseeing the unforeseen complications — that’s why they’re called unforeseen — and when we double our estimation we’re hoping account for some of those invisibles.
It’s a brute force option and won’t fix everything, but, if you only have time for a band aid you can give this one a try.
2. Plan With an Accountability Partner.
Talking through your project with someone else pulls out assumptions you didn’t know you were making.
One of the trends in the research here is the difference between an INNER view on project planning and an OUTER view on project planning.
We get stuck on the inner view, where we’re very optimistic and where we don’t tend to interact with REALITY very often.
When you talk with someone, communicating what you’re working on, how you’re going to do it, etc. — even if the person you’re talking to doesn’t know anything about your project — you will start seeing what was invisible before. The OUTER view starts infiltrating the INNER view.
But this one’s hard to start. If you’re anything like me you’ll resist it. However, if you can schedule a weekly call with a friend and get’r done you’re going to save yourself so much pain in the end.
3. Reverse Engineer a Truly Minimum Viable Product.
I wrote about this on an article here before but the gist is this: do you really know what it is you’re trying to do? Are you concrete about this project? Do you know what it will look like when it’s finished?
Maybe what you’re working on is ACTUALLY version 2.0 or 3.0 and you need to get back to a ruthlessly focused version 1.0 where you can be 100% clear on what the project is and how to do it.
I lay out steps for how to do that in this article: How to Deconstruct A Truly Minimum Viable Product
4. Keep a Daily Productivity Journal.
On episode 99 of our podcast, I interviewed two writers about how they do their daily productivity journals. What they do is so simple, getting started with it is so easy, but the results are massive.
For myself, this has made the biggest impact on my time estimates — bar none — because it helps my inner planner see the reality every single day. With all the interruptions and unforeseen circumstances, the blog I wrote actually DID take me 7 hours to write, instead of the 3 hours I thought it would take.
You can learn exactly how to do this here: 2 Experts Share Exactly How to Use a Productivity Journal (& Increase Productivity by 23%) FS099
5. Rediscover Why You’re Doing This Project
When you forget the point of the project you’re working on, it can flatline, stagnate, and feel really heavy.
I’ve had projects stall out for months and months, growing dust and weeds as I distract myself from it.
Often times it’s interacting with my audience — the people I’m making that project for — that helps me rediscover the purpose for my projects.
At Fizzle we have these forums where we’re always talking with one another, and when I read Fizzlers’ stories about building their company, how hard it is, how sweet the victories, how fragile the balance of staying motivated, it reconnects me to the mission, the purpose for my work, reminding me that there are people out there struggling with something I CAN HELP THEM WITH, and that’s when I discover if this project is important or not.
Who do you serve? What mission are they on that you can help them with? How can you reconnect with them?
And if you don’t know the answers to those questions you need to go through the Defining Your Audience course inside Fizzle.
Better Work
Use these 5 methods to plan your projects more realistically. My hope is that we can all stave off anxiety and set better expectations for ourselves.
From what I’ve seen working with loads of indie entrepreneurs, and from being an indie entrepreneur myself, if we set better expectations for ourselves, we’ll create more space to do better work.
Learn how to set goals that actually stick!
The Top 10 Mistakes in Online Business
Every week we talk with entrepreneurs. We talk about what’s working and what isn’t. We talk about successes and failures. We spend time with complete newbies, seasoned veterans, and everything in between.
One topic that comes up over and over again with both groups is mistakes made in starting businesses. Newbies love to learn about mistakes so they can avoid them. Veterans love to talk about what they wish they had known when starting out.
These conversations have been fascinating, so we compiled a list of the 10 mistakes we hear most often into a nifty lil' guide. Get the 10 Most Common Mistakes in Starting an Online Business here »




I have taken number 4 and RUN with it. I’ve been doing it for about a month or so. I haven’t actually done more, but I FEEL so much better at the end of each day. I don’t have a weekly check in/out ritual like you guys do. It’s very interesting how different these two very similar tactics can be. xoxo
I struggle with this all the time even when doubling estimated time. Love these tips, particularly number 5 and I’m now going to treble estimated time ;-)
This is so good Chase! Estimating how long things are going to take me is a HUGE issue for me, and causes a lot of lateness. Which as you mentioned, sends me into some really unpleasant anxiety if I’m not careful.
I guess I feel that when we give ourselves a long period of time to complete a project, the work will expand into that timeframe. So I always want to aim for faster completion dates to avoid that. Yet I almost never meet them. Hmm….
I loved the productivity journaling episode, and I definitely want to make that a habit. I think the safest thing for now is going to be also doubling my estimations for now, especially when it comes to client work! Thanks for the video!
Excellent video (although I should admit Chase, very entertaining ;- ) I’ve been doing project management most of my life and it is unbelievable how complicated thing could get. But again you debug, debunk, and deconstruct what good planning is all about.
I totally suffer from excessive optimism. I’m dealing with the aftereffects of it right now. Too many projects in a suddenly crammed schedule. The blocks on my calendar just aren’t big enough. Time to double up!
Raise your prices.
Oh I’ve been at this for so long and I still don’t have the inner view nailed down, but I’ve been required to estimate billable hours since, like, there was, like Tears for Fears. (fine, go look it up)… I’m still only about 50% on time with stuff unless I pad it. But that’s good for me. I started this comment 5 minutes ago and this is my third revision. Anyway–I have a TIP: I once was the marketing manager at a home remodeling company where owners were great salesmen. I learned this saying: “It usually takes twice as long and costs more than you think.” See, there is a Home Improvement Fallacy too. One more: my VP of Creative at a past agency understood. “Creative work takes as long as it takes. If they ask you how long, ask them what their budget is.”
Those are great tips.
Especially for those of us (everybody) who want to rule the world.
Yes. Yes and yes again! I’ve found the only way I can best manage this is the schedule less in my calendar. And even then, something I did on Monday took 2.5 hours when I had budgeted only 1 hour. But that task was the most important one of the day and I still managed to accomplish 2 out of 3 planned projects that day.
The daily review helps because you will more quickly see if you are over booking yourself and over estimating.
Thanks for a great article, Chase!
Darren it was you that sent me to that planner tool from someone (sorry I think it was Dinsmore maybe?) in which Tony Robbins was quoted as advising most of us can not complete more than 3 meaningful to do list items in a day. LIGHTBULB. Then as Chase says here, if I say okay I’ll write 3 pages, 2 hours each and STOP I’m so much better. I will usually work 6 – 5 so 6 hours of supposed work in 11 hours lets me probably get done, plus pee, eat lunch, do some planks, take a call and scoop the cat poop. Yep it’s that fascinating.
Faith, yes I’m quite sure it was the 2014 weekly planning tool that is updated every year on the live your legend website.
I took a course earlier this year with one of the guys in my mastermind called, holistic productivity. One of the many things I started to do was to make use of technology to enhance as opposed to slow down my creativity and production.
Just before I started the course I make sure I finally read David Allen’s book, getting things done. One of the most important things that is stressed in the GTD method is that your brain is meant for thinking, not storing ideas. So you need to have a well-managed inbox, filing system, or digital means to capture and brain dump all your ideas. You do NOT want to keep them in your head, but you also don’t want to forget.
This can take some getting used to but five proving to myself that it works. I use a combination of my calendar, Evernote, OmniFocus, One Note, and my phone. Every day or at least once per week I collect all of my random thoughts and organize them.
I also learned about two months ago that I was putting too much in my calendar and just looking out it cost me to freeze up. So now I book fewer projects, and if I complete them and want to keep working I can review my projects and tasks in OmniFocus or just take a break!
Thanks Chase. The Minimum viable product struck a nerve with me. I, like many others are trying to get to that 3.0. We are better off taking action and getting a decent working version out there. The 2.0 and 3.0 will come! Thanks again!!
Of course, if I feel a project will take (2) hours, and I plan (4) hours, aren’t I setting myself up for it to take (8) hours?? :) My tip: I’ve found it useful to stick with the time frame I set, and simply keep reminding myself that my goal is “completion, not perfection”. That has helped me stay on track like no other strategy. Love the video Chase! Thank you!!
Planning is important…but so is execution. I work much better when I time myself using something like Toggl…there’s something about hitting a switch and seeing the numbers start to increase that really gets me moving…may help for others as well :)
(oh, and great post btw!)
Shoot me NOW!
That book I promised my audience would be out over the weekend… Still not done. And, the next two days are 10 hour days for another project.
Big problem.
Oh yeah, email is up to 500 unread because last month I was trying to put every free moment into the book.
Thanks for the new tips to try with planning my next phase of my product. Another thing I am trying is to “time box” milestones and have buffer times between every 90 minutes. Not sure what the results will be, but it sounds like something worth testing.
I should mention, I do check my emails for important ones coming in. If I don’t see anything that looks urgent, I get back to work.
CHAAAASE! Where do you find the little drum beats you mixed in your video? I’ve been looking for that kind of audio tracks for a loooong time!
These are all little loops from Apple’s loop library, the one that ships with Logic, Final Cut Pro, etc.
Geniusss!
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I think I’m going to have to be one of the people who poo poo point 1!
Don’t add time or money, add confidence. Stick your estimates into something like this – http://www.juicysatsuma.com/costings/ – and push the confidence slider right until you’re happy.