Dead Lined
The fastest cure for overthinking, over-polishing, and over-engineering.
“I can have that to you by Friday.”
I INSTANTLY regretted saying that the moment it left my mouth.
During a client meeting for a new project requiring a full change plan, I did the Gantt chart planning in my head. I knew this work would take serious Leanne brain bandwidth.
My final book manuscript was also due the following Monday morning - so aiming to submit a client deliverable after that made a lot of sense.
Instead, I declared, “I’ll have that to you this Friday!”
Whyyyyy?
If you've ever said something similar and immediately regretted it, you're not alone.
For me, it comes down to a toxic combination of people-pleasing tendencies and a genuine addiction to pressure. Nothing mobilises me more than the stress of a looming task. If there was no pressure, I’d literally just bed-rot all day with my sausage dog.
Btw, the etymology of the word ‘deadline’ is pretty horrific. It originated in American Civil War prisons, where the “deadline” was a physical boundary. If a prisoner crossed it, the guards were ordered to shoot.
If you crossed the line, you died.
(On an aside, have you noticed how aggressive business language is? We have bullet points, target markets, headhunting, we ‘tackle’ tasks, ‘trigger’ workflows, have ‘frontline’ leaders, and we’re all just ‘killing it’?)
My Friday commitment isn’t life-or-death, but I act as if it is, because what do you have to lose?
Oh, you know, just trust, the single-most important commodity in a service-based business.
Anyway, I’d like to think one day I’ll change my behaviour and not set ambitious timeframes. But I don’t think I’ll ever change.
I got the change plan done, went on a boat + 6-hour champagne blitz for my friend’s b’day, and also submitted my book manuscript on time (here’s my post-celebratory LinkedIn post).
Yup, it sucked a little, but even after going through all that, have I learnt anything?
Nope! And it’s because - I adamantly believe there’s upside to setting a tough time-frame for yourself.
Example:
I recently looked up a guy I follow on LinkedIn to see if he had a regular Substack newsletter.
He does, but his bio reads: “I only share posts on Substack when they’re worth posting.”
His last post was back in January.
This can be a bit of a trap and there are two ways of looking at it:
Be like this bloke and wait for a “great idea” before sharing it. If I lived this way, you’d never get an email from me, because what does a ‘great idea’ actually look like? Who decides? Then, let’s say you wait 3 months before sharing something with your audience… It better be an absolute belter of an idea - they’ve been waiting MONTHS to read it. I find this approach creates more pressure.
Set a hard, specific deadline, like 5:50 am every Friday (the deadline for this weekly letter to you), and share what’s top of mind. This reminds me of my favourite Seth Godin quote: “Saturday Night Live doesn’t go on at 11:30 p.m. because it’s ready. It goes on because it’s 11:30 p.m.”
The other week, I almost skipped writing to you.
What was most top of mind was my Achilles injury ( boring). However, this Achilles post became one of my most “hearted” articles (thank you!). I got phone calls from lovely people checking in, very kind emails, and even an invite to speak at a national podiatry conference.
The magic of a deadline is that it helps to mobilise you.
Disclaimer: I’m not endorsing burnout hustle culture type commitment, where you lose sleep over what’s ahead of you and are frazzled 24/7…But just giving you a different perspective to consider when planning out your time, and asking a new question: Do you REALLY need an extra few days, or weeks… What would it look like to produce and ship something right now? And using that feedback to improve whwat you do?
Here are three ideas on how you can use deadlines to your advantage
Use pressure to say goodbye to perfectionism: A tight timeframe is the ultimate antidote to tinkering. When you only have until Friday, you are forced out of “perfect” mode and into “good enough” mode - which, most of the time, is exactly where you need to be. The next time you’re tempted to push a deadline back, ask yourself honestly, How much better will this actually be if I take an extra two days? The answer is usually “not dramatically better.” An aggressive deadline forces you to deliver the 80% that matters, drop the 20% that doesn’t, and move on to the next thing.
Own your calendar before you commit (ha! This lesson is written for me) Before you agree to any deadline, open your calendar, and make sure it’s one calendar that holds both work and life. I throw everything into a single Google Calendar: car servicing, appointments, dog walks, social events, all of it. Once you’ve committed, work backwards. Block out the actual time to do the thing. If I’m speaking at a conference on 21 July, I’ll add at a minimum two hours on 21 June to map the idea, two hours on 7 July to develop it, and two hours the day before to pack, practise, and rehearse. I share more on that in this episode 🌴55. Leanne’s (boring) way to manage overwhelm
Manufacture the pressure. If you don’t have a deadline, make one up. I mean, aren’t all deadlines simply made up anyway? I think this is why there are so many meetings - a meeting is usually a manufactured deadline to force us to produce something before we walk into the room. It’s the same principle that mobilises you to clean your house before the cleaners arrive. If you’re procrastinating on something, make it public. Book a meeting to review the work, or send an email saying, “I’ll have this to you by Thursday at 3 pm.” Always share a specific time.
What’s a ‘fake’ deadline you’ve set for yourself that actually worked? Let me know in the comments.
Which brings me to my own manufactured deadline.
It’s my 7-year biz-aversary, and I’ve been meaning to consolidate everything I’ve learned about workshop design, marketing, and solo business systems into one place. If I didn’t set a deadline, I’d be tinkering with this idea until 2028.
So, I did what I always do: I over-committed, made it public, and put it on the calendar.
I’m calling it The Best Of (7 Years Distilled) - three live virtual sessions across three consecutive Fridays (April 24, May 1, and May 8), starting at 9am AEST.
I’m going to share the exact frameworks that built my business, saved my sanity, and generated real ROI.
Grab the full bundle of 3 sessions for US$180 + tax, or individual sessions for US$100 + tax.
Or pick the single session that excites you most right now:
→ Session 1: 90 Minutes to Design High-Ticket Workshops - April 24
→ Session 3: 7 Years of Profitable Solo Business System - May 8
What’s a fake deadline you’ve set for yourself that actually worked? Let me know in the comments.
And do you also over-commit in the moment, or is it just me…?
🌴
Leanne “Chronic over-committer” Hughes
P.S. If this lands for you today, tap the heart 💙. That little click helps my ideas reach the next person who needs it.
I feel this in my bones, I’m exactly the same! And I also will never change. I’m often asked how I do so much and it’s because I cram it all in to insufficient time, and scramble to deliver it all
I love this Leanne! In a year 11 classroom the other day I got asked why they have to write an essay under pressure and to a deadline. I told them almost exactly what you’ve written here - with extra time their work wouldn’t be any better, they’d just start later and ultimately do the same work in the same time. But without all the “extra” (which is usually unnecessary).