Sabotaging Future-Brian

I’m never kind to the future version of myself, Future-Brian. I give enthusiastic Yes! answers to any request that comes my way and when the due-date gets close, I ask myself, “Why did I take this on?”. Why didn't I push for a smaller version and iterate? If I need help with this and I know the right person to help me, I find it hard to ask. Asking for help in two weeks time is much easier than asking for help before Friday.

My to-do list has been steadily growing since my first day at the company. I constantly underestimate my workload. “You want me to do this in a month's time? Sure! I’m bound to have more time by then.” My initial reaction is to say yes, and to get back to whatever I was working on. It’s not a conscious thought or deliberate choice, just an ambitious gut feeling.

George H. Alexander, Decorated Cast Iron Clock

Don't blame Present-Brian

Luckily, I don’t need to beat myself up. This is a real phenomenon, there’s even a name for it: hyperbolic discounting:

Individuals using hyperbolic discounting reveal a strong tendency to make choices that are inconsistent over time – they make choices today that their future self would prefer not to have made, despite using the same reasoning.

Hearing other people also trying to sabotage their future-selves makes me feel much better. Being aware of the problem makes it something I can fix.

Rands perfectly describes the situations I create for Future-Brian as the 4am panic:

It’s a definitive characteristic of the people I work with that they sign up for too much. They’re optimists. They believe they can do anything. They’re eternally growing. That’s the poetry, here’s the reality.

He gives great advice on dealing with the reality, but how do you avoid it in the first place?

A happier Future-Brian

I've made life easier for my future-self by better understanding what I need to do and what my priorities are. Trying to add something new to my list forces me to figure out where it fits, though I still don't get this completely right.

It's not too different from how a good team build product. There's a roadmap, and it's flexible, but adding something new has to push something else out. Raising the priority of one item will delay everything after it. If it's important to do multiple things at the same time then they need to be made smaller.

Taking time to curate a personal roadmap means I ask the important questions up front:
- Is a smaller first version ok?
- Does this trump another task I've got?
- Who will I need to help me and when do I let them know?

Having more time allows me to ask the critical question: Is this important? Does it solve the right problem? I find it hard to ask that question when I'm a few days from my deadline. If I start questioning its value, I worry I'm making excuses for myself.

Focusing on what’s important means my personal roadmap has to be lightweight. I've tried more to-do lists than I’d care to mention, but they've all had some friction with how I work. Trello fits my needs well.

Here’re the lists I use right now:

  • This week. All the concrete tasks I need to do. There's usually more than one week of work in here (I'm an optimist), but it feeds my Today list.
  • Today. What I need to get done before I go home today, in order of priority. At any time I know exactly what I should be working on, making procrastination harder. I try to decide this list first thing in the morning before I've got stuck in to my day. Something about my walk to work sets me thinking clearly.
  • Scheduled. I'm a manager. I go to meetings. Some tasks can't be progressed until I've talked with someone else. Having tasks in my list that I can't make progress with doesn't help my procrastination habit. If I was an engineer again I'd probably call this list Blocked.
  • Done. It's a good feeling to look back on a week of completed work. I struggled as a new manager to know what exactly I'd achieved all week. Achievement as a manager feels different than achievement as an engineer. The done pile is good reassurance I’m doing what matters.
  • Inbox. I work with a lot of smart people; they have good ideas and suggestions worth implementing. Prioritising these takes time, so they go into an unsorted holding pen. That way I can focus on capturing the idea, without deciding on a firm plan.

A happier Future-You

There’s no one-size-fits-all approach to managing your future self. What works best for me won’t be best for you. Research, experiment and iterate to figure out how you manage your attention. I learned it’s important I have multiple lists I can update from anywhere. A notepad that’s always in your pocket, post-its on your laptop, a single sheet of paper per day - any of these might suit you better.

What tips do you have to share?