Written by: July 20, 2024
5 steps to manage yourself (and follow through on your goals):
Principle-First
Deadlines are effective for getting things done.
Consider your remarkable ability to turn in an academic assignment just minutes before it’s due, regardless of what the night before required.
This is Parkinson’s Law in action, which states that work expands (or contracts) to fill the time allotted for completion.
Meeting deadlines set by teachers or bosses is one thing. Meeting deadlines set by yourself is a whole different challenge.
These could be self-imposed targets, such as launching a side hustle, choosing a therapist, or having a difficult conversation (to name a few).
Today, I’ll share simple strategies to help you conquer these ever-important, ever-elusive, self-imposed deadlines.
SUPERHUMAN SCORING
In every edition of System Sunday, I assess the featured system across three superhuman dimensions: impact, setup, and maintenance.
Unlike your typical review, I focus on factors that influence personal growth. Get to know the evaluation system.
Impact (9.5/10)
Back in 2021, I was working full-time as a management consultant. During my journaling one morning, I had a vision for the newsletter you’re reading today.
I’d always been good at meeting deadlines set by others—whether parents, friends, teachers, or bosses. (This likely stems from my people-pleasing tendencies.)
My identity was someone who could ”get stuff done.” So, I figured the launch of this newsletter would be no different! I set a deadline for launching my website and newsletter in 3 months.
Then, entire months went by without working on the project. It took me a full year to finally launch my website and newsletter.
The lesson I learned: I could thrive in structured environments, but managing myself was a whole different ballgame.
After 9 months of setting (and not meeting) that deadline, I realized I needed to create my own structure. Without it, my dream of launching this newsletter would never come true.
The lessons I’ll share today are especially helpful for freelancers and entrepreneurs to manage themselves.
But know this: setting deadlines is valuable in all areas of life—whether preparing for an athletic competition, becoming debt-free, or even removing yourself from a toxic relationship.
So here are 5 tips to follow through on your deadlines…
Setup (7.0/10)
1. Have a Strong, Self-Generated “Why” for Your Goal
Purpose is a powerful fuel source.
Get clear about what you are moving towards and what you are moving away from.
Consider the following 2 questions to clarify your “why”:
- Towards: What positive benefits will achieving this outcome bring into your life?
- Away from: What challenges, frustrations, or negative situations will this help you avoid or eliminate in the future?
In the case of launching my newsletter, I was moving towards contribution, control over my time, and meeting other creatives who inspired me. I was moving away from corporate politics, long workdays, and unnecessary Zoom meetings.
2. Set a SMART Goal and Track It
Let’s say you want to get into the best shape of your life.
A SMART goal could be: “I want to lose 10 pounds in 7 weeks by Sept. 7th.”
- Specific: Lose lb
- Measurable: 10 lb
- Achievable: 1-2 lb/wk
- Realistic: Y
- Timely: Sept. 7th
As Peter Drucker once said, “What gets measured gets managed.”
3. Pay for Things in Advance
The sunk-cost fallacy says we tend to overvalue things we’ve already invested time or money in.
You can use this bias (in your favor) to improve the odds of follow-through.
By paying for things in advance—like a gym membership, restorative vacation, or software to power your new startup—you’ll be more likely to take (and continue) the desired action.
I love this strategy because it flips the script on behavioral psychology—taking a bias that usually works against us into one that works for us.
4. Chunk Down the Task and Schedule It on Your Calendar
Break your big projects down into smaller components.
For example, if you want to start a small business, the first steps involve: opening a bank account, forming an LLC or getting incorporated, and signing up for a service to take payments.
Instead of using a to-do list, schedule everything in your calendar. I use Google Calendar (it’s free).
An HBR-backed study ranked time-blocking the #1 most effective productivity “hack” of 100 tested.
5. Use an Accountability System
StickK allows users to set a public or private commitment and add monetary stakes to increase accountability. One notable feature is setting negative stakes: if you fail to follow through with your commitment, you can tell StickK to donate money to a cause you dislike.
Most people will take extreme measures to avoid the “cognitive dissonance” of donating money to a cause against their identity.
For example, perhaps someone is an avid fan of Arsenal Football Club AND wants to exercise four times per week. They might create stakes to donate money to Chelsea Fan Club (an intense rival) if they fail to hit their goal.
What stakes would motivate you to follow through?
Maintenance (8.0/10)
The #1 dream killer is Goal Erosion. It occurs when you either lower your target or move your target further into the future. Sadly, some individuals let their dreams erode for an entire lifetime.
If you’re not on track to hit your deadline, you don’t necessarily need a new deadline. You need a better system to meet it.
That might mean allocating more time in your calendar (see step 4). Or it might mean designing your environment to avoid distraction (such as hiding triggers for bad habits).
BRINGING IT HOME
Summary of conquering self-imposed deadlines:
- Have a strong, self-generated “why” for your goal.
- Set a SMART goal and track it.
- Pay for things in advance.
- Chunk down the task and schedule it on your calendar.
- Use an accountability system.
A systematic approach (like this) requires more upfront work.
However, it’s a worthwhile investment. I’m so grateful I stuck to that second self-imposed deadline and launched this newsletter.
Today, you’re reading edition #125.
In the words of David Foster Wallace, I wish you way more than luck…
I wish to give you the tools to engineer your own luck, to follow through on your self-imposed deadlines, and to turn your dreams into reality.
All systems go,
2 MORE WAYS I CAN HELP YOU
Creator Method [Digital Course]: This is the system I used to grow an audience of 1M+ in under one year. Join 1,450+ students in this 5-star rated course.
1:1 Coaching:
