Starting New Habits

Some practical tips for starting new positive habits, and designing your environment and daily actions to support you in them:

Life wants you reactive. Defy its expectations.

World-upending events sure have a way of scuttling our best-laid plans. They can disrupt, test, and potentially demolish the systems we’ve labored to put in place, leaving us reeling and unsure of both our former goals and the tools and processes that we’ve long relied on to achieve them. In the strange and unfamiliar new world we find ourselves in, a way forward that may once have been at least somewhat clear can be suddenly hard to see.

Yet while 2020 has been extraordinary in the cascade of hurdles it has sent our way, on reflection I think it’s the concentration and intensity of the challenges that’s been unique, more so than their intrinsic nature. Old problems can easily reassert themselves in new ways that require us to adapt our tactics, without necessarily changing their fundamentals. All of this has brought to mind one of the most important lessons I’ve learned — one that I’ve come to appreciate now more than ever: the profound value of maintaining an active rather than reactive stance, of taking the reins of life rather than falling into the default habit of merely responding to outside forces.

Even before this year threw its worst at us, keeping one’s bearings and navigating life actively was a challenge. The never-ending stream of emails, texts, and social media posts that inundate us, the mobile devices that keep us connected and receiving them at all times, and the expectation that we keep up with all of it, have made it easier than ever to fall into reflexive reactivity. Life will hand you an unrelenting “To Do” list if you let it, cobbled together from others’ priorities, and it’s perilously easy to fall into the trap of continually responding to those external demands without giving due thought and precedence to your own most important values and goals. Even in normal circumstances, your carefully and intentionally curated “To Do” list can become cluttered with minutiae that make it hard to see through to your main objectives and keep them in the forefront of your thinking and daily actions.

Enter a world where existing plans are out the window, new plans have become extraordinarily hard to make with any degree of confidence, and we look to daily briefings and decrees to tell us what’s next, and you have a situation where seemingly every process you’ve put in place, no matter how carefully focused or finely tuned, starts to break down. In an environment of fearful uncertainty that’s cultivated by a relentless, 24/7 news cycle and the social media streams that amplify it, it’s far too easy to become overwhelmed and immersed in a toxic, bogged-down morass of uncontrolled reactivity. You may well sense that the intensity of the howling wind you walk into, and the drag that you must overcome to move forward, has increased.

Amid this intensified sound and fury, it’s become more vitally important than ever to live with intention — to remind yourself of your purpose, to maintain and trust in your bearings, and advance toward your objectives in whatever ways you can manage to, with steady, unrelenting determination. In the face of a louder-than-ever storm of demands that you respond, react, panic, submit, and divert from your chosen course, you will need to resolve, with some serious commitment, that you are going to keep going.

To be sure, these are not “normal” times. They require us to flex, adapt, and re-assess processes and short-term plans that, for the moment at least, may no longer apply or seem relevant. But in so doing, we’re also challenged to take stock of what is most important to us in the long run, and work to actively maintain our focus on it — to tune out the world’s relentless, panic-inducing sound and fury when necessary, and find and cultivate the resilient and immutable within ourselves.

I’ve written this as a reminder to myself as much as to others. Now is the time to find and tend to that indomitable spark within yourself, to keep your inner fire lit and press on toward your most important goals with calm, steady determination. When life knocks you down, it’s time to stand up and get moving again.

My goals for this site remain very much the same — to share useful knowledge. And while these challenging times may warrant re-examining tools, ideas, and practices to adapt or discard what is not currently practicable, the vast majority of what I’ve had in mind to write about here (38 more post ideas in the queue and counting) remains as relevant as ever. I very much look forward to developing and sharing that material here, and I hope you’ll enjoy the journey with me.

#MindsetReset Take-Home

Two enduring takeaways from the #MindsetReset program I completed earlier this year:

1. The practice of sitting somewhere away from a computer to fill out a “5-Second Journal” page has earned a lasting place at the top of my morning routine. The high bar the 5-Second Journal template sets of having to choose just one top project for the day has been particularly helpful in forcing me to focus judiciously. I’ve found that I need that, as I otherwise tend to get bogged down in the details of my beautifully organized but often overly abundant “To Do” list — which, while indispensable, is in some part just an overwhelming inventory of “I should”s that can make me miss the big picture of my most important goals if I let it.

As time goes on, I’ve started to experiment with small additions to the template Mel provided and my routine of using it. For example, I’ve found value in the 3-item “mental inventory” practice I saw recommended somewhere (unfortunately, I’ve lost track of the source), which consists of writing down:

  • what I’m working on
  • what I need to be working on
  • what I want to be working on

This bit of reflection seems very effective at helping me get perspective and orient my priorities, both for the immediate moment and with my long-term goals in mind.

2. I’ve developed much stronger discipline with my phone at night, and constant awareness of it as a tempting potential detriment to getting the good night’s sleep that I need to be able to be my best. I don’t go so far as to keep it out of reach, but I restrict my use of it to listening to relaxing music, a meditation app, or a podcast (usually self-improvement stuff, such as the last #MindsetReset video, keeping the screen face down), to help me either get back to sleep or make productive use of the time. I’ve found I need to be open to flexible approaches in my lifelong battle with insomnia. Good sleep is always my first goal, but if I’m too alert for that, I try to at least make good use of the hour or two until I can get there. Overall, I am sleeping better thanks to the improvement in my phone discipline; it’s been an observable win.

A Foundation for Capture and Review

Establishing a centralized place to consistently gather and review my intentions has been a key part of my recipe for achieving my goals and getting where I want to go. “To Do” lists aren’t a particularly glamorous thing, and — as I’ll get into in a future post — my end objective is emphatically not the mundane, mechanical fulfillment of endless lists of “To Dos”. But designating and maintaining a single place to collect and organize the next steps and perceived obligations in my head has provided a truly indispensable foundation for my higher-level pursuits.

I’ve used various methods and media over the years — from handwritten checklists in the annual planners where I kept track of assignments in college, to a Palm III and the Windows-based Palm Desktop app that aided my late-90s stint in the videogame industry, to my system of the past 15+ years: becoming an enthusiastic user of Things on all my devices. Whatever tools and process you use, having a consistent system for capture and review seems essential to focusing effort effectively and thereby reaching the life and work goals that matter most to you.

Having clearly thought-out objectives is essential to choosing a successful approach for any endeavor. My purposes for maintaining a “To Do” system are:

  • to fulfill the commitments I make
  • fo fulfill my own intentions
  • to be reminded of and achieve my most important long-term goals
  • to ensure I prioritize well and put each day’s time to good use
  • to unload my mind and thereby reduce needless worry, while clearing the deck for more useful applications of mental power

This last is a key feature of the process, whose benefits I’ve really come to reap and appreciate over the years. Having a place to unburden my restless mind has greatly reduced my levels of counterproductive worry. To some, this constant activity might look like stress-inducing obsession, but when I write things down as they come into my head, in a place where I know I’ll review them later, I enable myself to let go in a very beneficial way. Once I’ve entered a thought into my system, I no longer need to stress about whether I’ll remember whatever responsibility or action it entails later. I can relax, exhale, and direct my thinking to more immediately useful pursuits.

This process of “ubiquitous capture”, which I’ve been practicing for as long as I’ve used Things, has been a great boon to my work and personal organization, and Things nimbly facilitates it. Its “Quick Entry” panel on my Macs, and Siri integration and sharing extension on iOS, enable me to very quickly capture stray thoughts without interrupting my flow. One quick global hotkey combination on my Mac, from wherever I happen to be, makes entering a new thought easy and instantaneous, without disrupting my thought process or flow state. I can take the time to tag and file the item then, or simply let it fall into Things’ “Inbox” for later review in favor of maintaining my enclosing train of thought. Speech recognition on my Watch, iPhone, and iPad offers “Hey, Siri: Remind me to …” as another quick and easy way to capture thoughts in the middle of whatever I happen to be doing. The results of this approach end up in a designated list in the Reminders app, from which Things can quickly and easily import, and I’ve just learned in the course of writing this that there are even more direct avenues into Things that I can start taking advantage of.

The usefulness of all this capture would be greatly diminished if it just resulted in a huge, unorganized pile accumulated in my “Inbox”. Thankfully, Things makes tagging and filing so quick and easy that my Inbox is completely empty most of the time, and very rarely contains more than a few items. On the Mac and iPad in particular, Things’ ample keyboard shortcuts make very quick work of applying tags, assigning the item to a “project”, adding any desired notes or sub-items, scheduling the item for a particular day or some unspecified time in the future, and adding an optional deadline. This all sounds like a lot of activity, but once you’ve mastered the keyboard shortcuts it can all be done extremely quickly.

Tagging items has become a particularly key and worthwhile part of the process for me, due to Things’ spectacularly useful and globally accessible support for tag-filtered searches. I make sure that every item that leaves my inbox has at least one appropriate tag applied — a consistent practice that has made Things the single most organized place in my life. With a simple keystroke, autocompleted search, or click of a tag token (on macOS), I can instantly slice through my tasks to filter down to a particular focus area — be it work at large, a particular project, phone calls to make, errands to do while I’m out, tasks related to my children and their school work, bills to pay, etc. The lasting rewards I reap from this instant filtering and recall capability make the small amount of work I put into tagging things eminently worthwhile.

Accumulating this info would be less useful, of course, if I didn’t have access to it everywhere I go. Things‘ fast and reliable cloud sync and presence on my iPhone, Apple Watch, iPad, and Macs has done a superb job of ensuring that I have my latest info accessible and editable always.

Things’ elegantly focused simplicity is a key feature for me. Some may yearn for attachments, geotagging, or the ability to style text. To me, what is absent is as much a part of its judiciously elegant design as what is there. What I specifically don’t want are features that tempt me into unproductive fiddling with my content when I have other things to do. I find just the right balance in the ability to add plain-text notes and URLs to items. Being able to link to stuff is made particularly handy by the way Quick Entry can instantly capture links — to a Web page I want to revisit, to an email message I know I’ll need to refer to later, etc. Any app that supports “deep linking”, such as the bug tracking system I use daily, can have its content linked to from a Things item, making recall of the needed info instantaneous when I go to tackle that item later.

The ability to schedule recurring items with appropriate deadlines has been another key feature for me. It’s a money-saver (eliminates missed bill payments) and is handy for reminding me to keep in touch (I make sure to call my 92-year-old Dad daily), keep to my exercise/training goals, and take care of more mundane stuff (like weekly meal planning and grocery shopping, remembering to start the dishwasher before bed, and getting garbage and recycling to the curb on the right days).

To its credit, Things doesn’t enforce a rigid or dogmatic view of how you have to organize your stuff. It offers a variety of useful tools (tags, projects, and “areas”) that support you in being as organized as you choose to be, on your own terms. I’ve tried a variety of approaches over the years — making greater or less use of projects and areas, for example — and found Things to be readily adaptable to the ways I choose to work.

Whatever tools or process you embrace, instituting a practice for capture and review is, in my experience, an essential cornerstone for pursuing serious goals. If your mind works anything like mine, the creative flotsam that drifts about it can benefit from some basic de-cluttering. Once unburdened from having to track life’s distracting, shiny minutiae, your brain will be free to navigate with higher purpose and get you where you want to go.

In future posts, I’ll get into the details of my own usage and review process, and look at the upper layers of goal-setting and pursuit that a “To Do list” process exists to support. Along the way, I’ll share some advice that I’ve encountered and successfully employed to keep my focus on what matters most.


Mel Robbins, who I first became aware of while surfing YouTube, has launched a program called “Mindset Reset” that is worth checking out. I’ve had good success folding some of the recommended techniques into my daily process, including the “5 Second Journal” morning practice (a worthy peer/alternative to the Tim-Ferriss-recommended5 Minute Journal”, which I’ve also used to good effect).

I found the ten-page guide’s 2018-in-review and 2019 planning prompts helped me put things in perspective and did a good job helping me focus down on a solid set of worthy goals for the new year.

One nice thing about Mel is that she pretty candidly relates her own daily struggles, as well as some fairly massive problems she’s had to overcome in her own past (such as bankruptcy and despair a decade ago), which tends to reassure one that this isn’t all pie-in-the-sky coaching with no grounding in reality and its myriad challenges. Mel’s recommendations are practical, relatable, and can be applied in incremental steps.

The daily installments of this 35-day program are being archived (see Mel’s YouTube channel for the videos), so you can try it out and benefit regardless of whether you started at the cusp of the new year. The entire thing is free. See for Mel’s intro video and to sign up for the emails that will get you started.

Blake Leeper: A Runner Without Legs

I can think of no better way to kick things off than with one of the most inspiring interviews I have yet seen.

My sons and I have watched this several times. It is worth every minute. There are many deep and universal life lessons in here, as well as a chance to see what it’s like for someone to face and overwhelmingly conquer an extraordinary physical hurdle – with relentless determination, and the greatest attitude I have ever seen in anyone.

Blake Leeper:


Welcome to a new experiment.

I’ve long taken an interest in the mindsets, practices, insights, and cultivated character traits that enable people to take command of their lives, overcome obstacles, expand their capabilities, achieve ambitious goals, and fulfill their highest potentials.

A lifetime of observation has persuaded me that the techniques and ways of thinking that produce success can be acquired — that they are learnable, and teachable — and it has long interested me to learn as much as I can from the methods and successes of others. Discovering kindred thinking in places like Tim Ferriss’ podcast over the past couple of years has added fuel to my lifelong interest in the subject, and prompted me to start this site, where I aim to share what I’ve absorbed and promote the great work of others that I’ve found useful.

Working to gain capabilities is one of the most valuable things you can do for yourself and those around you. It builds versatility, resilience, independence, and autonomy, fosters a culture of competence, and paves the way for you to build the life you want.

I’ve combed through a lot of material, in late nights on YouTube, bouts of podcast-ameliorated insomnia, and reading online and off-, taking notes and searching for ideas, approaches, and techniques that have the most usefulness and applicability. My aim here is to distill the best elements of what I’ve learned into concise and useful gems that I can pass along.

I won’t hold myself up as an example of optimal productivity by any means, nor can I promise some overnight recipe for instant success. I find myself regularly humbled by my own shortcomings. But I am on the journey, continually striving to learn, and I make it my goal to improve a bit each day, week, month, and year — to learn from success and failure alike, and incrementally refine and augment my methods. I find regular contact with reality to be the most salutary thing in the world for productivity fads and abstract theories about how to accomplish things. I mean to keep my practice and recommendations firmly grounded in the invaluable feedback that such trials-by-fire provide.

If these things interest you, then I invite you to keep an eye on these pages, where we may strive and learn together. With a determined perspective, every challenge becomes a valuable opportunity to able up.