Tag: Derek Sivers

  • The Realized and the Wistful

    “If more information was the answer, then we’d all be billionaires with perfect abs.” ― Derek Sivers

    We know we’ve got to work the plan to meet our objectives. Plans without work are simply dreams that will eventually be wistful regrets. I write a lot about productivity to remind myself that becoming is an act of deliberate action. Everything else is talk.

    As Jim Collins demonstrated to us with his analogy in Good to Great, pushing the flywheel establishes momentum. In theory it becomes easier and easier as we push and the flywheel’s momentum takes over. The opposite is true as well: stop pushing for awhile and all momentum is lost and the work becomes harder to get back on track. The lesson is to keep pushing. The underlying lesson is to make sure we’re pushing on the right flywheel in the first place.

    It’s essential to assess things as we go so we don’t arrive at the place we’ve been pushing towards only to find it wasn’t where we wanted to be in the first place. I had a few people question me when I stated I was assessing whether to keep writing this blog. I think it’s fair to ask that question of ourselves, but maybe not fair to put it out there in writing for all to see. Perhaps I overshared. Still, I keep pushing.

    The root of the Sivers quote above, and the conclusion I’m finally getting to, is that we’re all figuring it out as we go. We can’t stop pushing ahead to establish and sustain momentum, but we must pause long enough now and then to assess where we are and where we’re going. There are no do-overs in this game, and nothing is ever perfect. But when we get it right, we might maximize our realized dreams while minimizing those wistful regrets. Maybe that’s enough success for one lifetime.

  • The Immediate Concern

    “A bad goal makes you say, ‘I want to do that some day.’ A great goal makes you take action immediately.” ― Derek Sivers

    I type this a little sore. All over sore, the kind that makes you move a little slower and assess your choices in life. Still, it’s a good sore of layered exercise expressing change in the body. We all ought to embrace such positive change in our lives. At least that’s what I’m telling myself, knowing I have work to do today to keep that momentum going in the right direction. And so I appreciate what Sivers is talking about when he assesses a good goal.

    The immediate concern is sustaining positive momentum towards the goal of completing a lot of mileage in a relatively short amount of time. To average 6.5 miles a day is a reckless goal at this stage of my professional life, but calculated to force me to row more often. I’m already feeling the effects of this, and I’m energized by the goal despite the fatigue it brings to me. We are made to move, not just sit staring at a variety of screens all day.

    When the summer is over, I’ll have kept my commitment to myself by keeping the goal alive to completion. Plenty of other things will keep me busy in that timeframe, but some things will be sacrificed for the greater good of finishing the goal. Life is full of tradeoffs, isn’t it? Why trade a good fitness level for comfortable distraction?

    At this very moment there’s a creeping urgency to stop writing about it and get back to stacking miles on top of what’s already been done. What doesn’t get done in July will have to be done in August, and frankly, I’ve got enough on my plate already in August. Great goals make you question your sanity while you’re making them come true. And yet, it makes you feel more alive than a less worthy goal ever would. It’s literally putting bold words into action. What’s more transformative than that?

  • Adding Surprise

    “If you keep experiencing the same things, your mind keeps its same patterns. Same inputs, same responses. Your brain, which was once curious and growing, gets fixed into
    deep habits. Your values and opinions harden and resist change.
    You really learn only when you’re surprised. If you’re not surprised, then everything is fitting into your existing thought patterns. So to get smarter, you need to get surprised, think in new ways, and deeply understand different perspectives.” ― Derek Sivers, Hell Yeah or No: What’s Worth Doing

    We know this, don’t we? To learn is to grow. To experience new and diverse things in our lives offers this learning experience for each of us. So it follows that we ought to get outside of our own small box and leap into the new and surprising. It’s here where we may just find delightful insight.

    Ah, but can’t we find delight in our everyday routines? Isn’t that why we’ve landed here? I may walk out into the garden and delight in new blooms, the smell of fresh basil, the song of a cardinal overhead. I can sit in a familiar chair practically molded to my form and read a favorite book again and again, drawing out something new from it every time. Indeed, there are advocates for immersing ourselves ever deeper into the familiar that we may one day master it. We can’t reach mastery if we’re always frittering from one thing to the next.

    There is of course a happy medium. We may go out and seek new perspectives and return to the familiar with them as a more experience-rich person. we collect memories and insights into the ways of the world and bring them back to build a bigger, more expansive and more open box. And like a bird nest we may fly away and return in the proper season. Life is about balancing the familiar with the surprisingly new. The trick is what to prioritize when in our lives.

  • An Expression of Yes

    “The price of greatness is responsibility over each of your thoughts.” ― Winston Churchill

    Yesterday, in a clear break from discipline, I took the dog to the beach for a long walk. I collected smooth stones until my coat pocket was full and stuffed a few more into my pants pockets. The pup—her tail wagging furiously—greeted other dog walkers and sniffed the salty foam. I might have been more productive pushing through some report or calling a few customers, but the pup and I agreed this was the most productive lunch meeting I’ve had in a long time.

    We know, deep down, when we’ve done our best. So many people go through the motions nowadays, not really finding the magic in the moment in their work. Not really feeling the power of contribution to something bigger than themselves. As if our days are infinite. As if staying within ourselves isn’t a betrayal of our potential.

    Betrayal of potential is doing work that doesn’t matter to us for a beat longer than absolutely necessary. I post this blog every day because it speaks to me, and I speak through it. Like flossing, when you diligently do it every day you get a positive outcome. Shouldn’t our primary work be the same?

    What does it matter to you?
    When you got a job to do
    You got to do it well
    You got to give the other fellow hell
    — Paul McCartney, Live and Let Die

    We have no time for trivial pursuits. We have no time for work that doesn’t resonate, that doesn’t make us feel something essential within ourselves. If today were our last day on earth, would the work we are doing mean a thing? To borrow from Derek Sivers, if the answer isn’t a hell yes, it’s a no. How many no’s do we want to stack in a row? Make today a yes and start a new kind of streak.

    Walking on the beach yesterday was an expression of yes. It was walking away from a no and making the most of a fragile moment. The work was still there when I got back, but it felt different than it did earlier in the day. It turned out the work wasn’t the problem, it was the worker all along.

  • Revisiting the 20/10 “Stop Doing” Exercise

    “Suppose you woke up tomorrow and received two phone calls. The first phone call tells you that you have inherited $20 million, no strings attached. The second tells you that you have an incurable and terminal disease, and you have no more than 10 years to live. What would you do differently, and, in particular, what would you stop doing?” — Jim Collins

    “If it’s not a hell yes, then it’s a no!” — Derek Sivers

    This idea of contemplating our expiration date (memento mori) combined with the possibility of having the financial freedom to do whatever we want with the time is an essential filtering mechanism for designing our future. It’s almost never about the big ticket money activities, it’s about carving out time for the simple things in life, like being there for the kids or having the lifestyle commitment and personal responsibility to get a puppy. Sure, money helps, but it’s freedom people seek in their lives. The fastest way to freedom is saying no to more things.

    We ought to remember we all have a terminal disease, whatever our timeline, and get busy prioritizing the essential over all the rest. Life is a short game, best fully-optimized. We’ll never fully reach that level of excellence, but we can aspire to close the gap. Instead of resolutions, we may choose instead to define what our “no’s” will be, that we may have the space for those “hell yes’s”

  • What You Put Out


    “Calling yourself creative doesn’t make it true. All that matters is what you’ve launched. Make finishing your top priority… When you’re gone, your work shows who you were. Not your intentions. Not what you took in. Only what you put out.” — Derek Sivers, How to Live

    “When you ship, you silence the lizard brain. You beat the resistance and your ideas get out in the world. It’s not easy, but it’s very important. I am shipping because I don’t want to create art for art’s sake; I want to do work that matters, that makes a difference in people’s lives. Not tomorrow, today.” — Seth Godin, The Practice: Shipping Creative Work

    Anyone who does anything creative knows the scorecard. What you intend to do has no place at the table: The only thing that matters is what you produce. If you don’t put it out there you aren’t a part of the Great Conversation.

    I focus a lot on productivity in this blog. More than some think I ought to. For me, productivity is the natural outcome of habits and routines and the gumption to click “Publish” every damned day. The lizard brain is a very real struggle, so is imposter syndrome, and so is the relative comfort of low agency. To overcome each of these hurdles, you must learn to be audacious. For most of us this doesn’t come in a spark of magnificent insight, it comes through incremental daily actions: teaching the brain that this is what is expected of it today and every waking day from here to the very last.

    This daily routine of writing profoundly changes you. I’d read that for years in Seth Godin blogs before I finally started posting regularly. I don’t look at my early posts often, for they’re full of typos and grammatical errors and run-on sentences (some things don’t change). But each brought me here. And here brings me to whatever comes next.

    What you consistently put out builds boldness and audacity and a blatant disregard for keeping up appearances. What I’ve learned during this dance with daily productivity is to avoid telling the world what you’re going to do. All that matters is what you have done. So by all means: ship it. Lizard brain be damned.

  • Getting to Deeper Work

    “In an age of network tools… knowledge workers increasingly replace deep work with the shallow alternative—constantly sending and receiving e-mail messages like human network routers, with frequent breaks for quick hits of distraction. Larger efforts that would be well served by deep thinking, such as forming a new business strategy or writing an important grant application, get fragmented into distracted dashes that produce muted quality…. Spend enough time in a state of frenetic shallowness and you permanently reduce your capacity to perform deep work.” – Cal Newport, Deep Work: Rules for Focused Success in a Distracted World

    I think the reason I get up early is to think, uninterrupted. And when I am interrupted, by other early risers or by something as simple as the cat meowing for food my own deep thinking is disrupted, often to a point where I have to put away the work and find a way to reset myself. The beautiful thing about posting a blog every day is I’m forced to find a way through the shallow pool I find myself swimming in back to deeper waters, distractions be damned. But the work never feels the same.

    Noise-cancelling headphones help a lot. When I go deep I’ll play the same song on repeat until I’m done with whatever project I’m committed to finishing. For me, two songs work particularly well for this, Mark Knopfler’s Wild Theme (no surprise if you know what my favorite movie is) and Claude Debussy’s Clair de lune because they both quietly soar and have no lyrics to draw me out of my focused state. After years of this trick, playing one of these songs becomes Pavlovian in snapping my mind to attention.

    Long walks in nature help reset the mind when you find yourself in frenetic shallowness, and I have my go-to spots for this too. Walking helps you sort out the puzzle pieces in your subconscious mind, putting all the pieces on the table and shuffling them one step at a time. If the walk goes well you sort things out just enough. But sometimes I find myself dwelling on another puzzle altogether, and realize the distraction wasn’t swimming shallow at all but this elephant in the room that you’ve got to remove before you can properly focus on the original project. Long walks help sift the pieces enough for you to see what you’ve been staring at all along.

    Another trick of the trade that countless brilliant minds subscribe to is strict daily application of Julia Cameron’s Morning Pages. Write whatever comes out of your mind onto the page for three pages in a gushing stream of consciousness until you’ve gotten all the noise out of yourself, and then shift to creative output. I’ve tried this a few times but find myself frustrated by the time spent on Morning Pages that I could be spending on the work itself. The fault isn’t in the process but in my commitment to it. Enough people swear by it that it must work, and to go deeper I might have to recommit to this process myself.

    “The way to live is to create.
    Die Empty.
    Get every idea out of your head and into reality.”
    – Derek Sivers,
    How to Live

    Whatever gets you there, deeper work is where we mine the very best of ourselves. Eliminate as many distractions as possible, retreat to your proverbial cabin in the woods and do the work. While there’s still time.

  • Give a Lift

    “You can’t actually pull yourself up by your bootstraps. Ultimately you are lifted by those around you.” – Derek Sivers

    It’s that time of the year when people are more open in expressing gratitude and displaying generosity. It’s a great time to take stock of who helps you the most and to express appreciation for that lift of the bootstraps they give you. And to look around and see who needs our help the most in lifting themselves up. The last couple of years haven’t been a cake walk, and there’s more people who need help than ever before.

    Give a lift to those in need. Lend an ear, or your time, or sure, sometimes a few bucks to help someone when so many are on the edge. You never know who needs you the most until you step in at just the right moment. As crazy as the concept might seem sometimes, we’re all in this together.

  • Killing Our Previous Self

    Sacrifice the things you used to believe, and the ways you used to be.
    Learning leaves a trail of little deaths.
    – Derek Sivers, How To Live

    The highest reward for a person’s toil is not what they get for it, but what they become by it. – John Ruskin

    We all transform into something different. This is the only way, for no matter how much we might embrace the comfort of our current self, it must ultimately die and be cast aside for the person we become by our actions. The question isn’t whether who we once were dies, but rather, who does the killing. Do we move ourselves towards that which we aspire to be, or does the world leave us behind, a shell of our previous self? Don’t let this happen to you friend!

    The pandemic killed more than the people who succumbed to COVID-19. It killed what was comfortable and routine for the masses, changing us in profound ways that we might not fully understand. But that death of our former self was going to happen anyway, it only accelerated in the pandemic. Mourn what has passed if you will, but then dust yourself off and ask yourself, what comes next for me?

    I mourn the passing of old friendships. People I was once close with who have disappeared down the path of their own lives. But then again, I’ve changed too. Learned new things, built new habits, formed new alliances. Our paths were once parallel and then diverged. Old friends might still gather and celebrate what once was, or look towards a place where we cross paths once again, but ultimately we must keep walking our own path, just as they do. Whatever will be will be. Should we meet again, wouldn’t it be better if we built a great story of how our lives grew in the time we were apart?

    Success is not to be pursued; it is to be attracted by the person you become. – Jim Rohn

    I celebrate the journey others are on, even as I continue on my own path. We’ll have so much to talk about, should we meet again. Stories about those long-dead former selves transformed into something different. Don’t we owe it to ourselves to make that story greater than what it once was? To learn and grow and follow the path that brings us the most meaning in our lives, and share this greater self with others? That, it seems to me, is what success really is.

  • Add a Question Mark

    Don’t accept the false stories people tell.
    Things are neither good nor bad — they’re as neutral as a rock.
    When people give opinions, add a question mark.
    If they say, “Immigration is bad,” change it to, “Immigration is bad?”
    Let the questions drift away, unanswered.
    – Derek Sivers, How To Live

    There’s a hidden message in this Sivers book that comes to you as you read it. Don’t take it all at face value. Question everything. Especially the very things you’re reading in his book. The advice feels both right on point and at other times the completely opposite of what you believe in your core. And that’s the point of it all. There’s no set way to live your life, question all advice and find what works for you.

    I wish more people would add a question mark instead of just blindly believing what they hear from people with accumulated connections, titles and degrees. They may be absolutely correct about a position they take, but it’s just a story until we validate it ourselves. The old expression, “Trust, but verify” comes to mind. Add the question mark to those statements and watch them transform:

    Vaccinations are meant to control people?

    Government serves people?

    There is only one true god?

    You must stick with one company to grow your career?

    You aren’t “qualified”?

    Tom Brady is the greatest quarterback of all time?

    See? Most people throw their beliefs at us to try to make it stick in our own mind. Adding the question mark is like spraying teflon on our skull, making us immune to questionable stories, and making us assess the validity of the feasible. Every statement above could be true, or complete bullshit, but we don’t really know which at face value. We must add the question mark, and in doing so, pause and assess the original statement. Or, for the truly outlandish, let it drift away.

    But Brady is definitely the GOAT. Right?