Ten Lessons from A Decade of Work and Play

I used to be embarrassed that my career path required a three-dimensional maze to connect the dots between jobs. Nanny, software developer, waitress, yoga & meditation teacher, organizational consultant?! Can’t you just pick something and settle down already?! But looking back, something more like pride sneaks in. The one thing I’ve done well, if nothing else, was to follow the thread of my curiosity. It has led me through twelve jobs, four states, two degrees, and one monastery, to say nothing of the incredible and inspiring people I’ve met along the way. 

Save one of the last ten years, I’ve set my own schedule and structured my own time. That’s taught me a lot about productivity and time management. I’ve learned a number of hard lessons that boil down to a set of key principles. Maybe they’ll be helpful to you on this wild and precious ride. Here goes!

1. Say Yes To What Brings You Alive
2. Learn From Doing (but don’t count paperclips)
3. Clean Up Your Mind (master your emotions and learn to choose)
4. Get Inspired (find what lights you up, and feast)
5. Keep It Simple (maintain a vision and don’t multitask)
6. Build in Structure (that anchors but doesn’t strangle)
7. Find Your Believers (stay close to people who believe in you)
8. Be Fearless & Kind (but not stupid)
9. Let Go (and let stay)
10. Decide What Kind of World You Want to Live In

Let’s dive into each of these in more detail. Read in full, or scroll to the number that get you most excited! I’ve included many of the tools and practices I use to stay sane and live a full life, as well as examples from my own life to drive these each home.

1. Say Yes To What Brings You Alive

Even if you don’t know why, how, or what if, be willing to say yes to opportunities that excite you. Say yes out of joy, challenge, curiosity, or any other value that floats your boat. Be true to the level of yes that you’re at. Are you at a hell yes? If not, find your way there. Maybe you don’t want to go on a date with that guy/girl, but you want to hold their hand and go for a short walk. Maybe you don’t want to commit to a full year, but you’re definitely down for 6 months. Be willing to offer and counteroffer, and home in on what it is that you want. The world needs people who are taking up their role in this life, doing whatever it is they are here to do, and doing it fully.

DON’T say yes out of fear, pity, or people pleasing. I’ve interviewed over one hundred candidates for a highly selective program with a very specific culture. One of the basic premises is that we are gatekeepers for the community. If we let someone in out of pity or obligation, we are both polluting the culture and doing a disservice to that individual who will inevitably be a poor fit. It’s either win-win or no deal. 

Be a gatekeeper for your own life. Who and what do you want inside of it? Who and what do you out? Make lists with two columns: “More of…” and “Less of…”. Keep them updated. Make your relationships and engagements win-win or no deal. That means that they’re a win for you, but it also means that they’re a win for whoever else is involved. Are you looking out for them? Do you know what they want and need so you can help them get it? Win-win or no deal. That said, you’re probably not going to get everything you want. Know what’s most important to you, and what you can let slide.

Whatever you’re doing, do it fully or get out. Which leads to the next principle…

2. Learn From Doing

The sage Clarissa Pinkola-Estés of Women Who Run with the Wind fame talks about a dangerous phenomenon called “counting paper clips”, whereby we sit around busying ourselves with useless tasks to distract ourselves from our real work. Let’s not do that.

I often get caught in indecision, and putter around avoiding my next step. I’ll find myself opening and closing random kitchen cabinets, pulling books off the shelf, or realizing I should do the laundry right now. I do these things to distract myself from the feeling of uncertainty, which is pretty uncomfortable for me. When I notice I’m feeling uncertain (or more commonly, I notice I’m opening and closing a bunch of cabinets or browser tabs), I pause and check in with myself. I find the root of the issue, and decide on an action plan, or at least a next step.

I have a habit of putting off completing applications, reaching out to someone, or finishing pieces of writing if I have even an iota of uncertainty. This has been immobilizing. Now, I keep moving forward. I send the email. I complete the application, I take the next step. Usually, these aren’t final decisions. I let myself get to the point where something has become a real option (like, once my application gets accepted and I’m offered a position) before saying no. And I’ll do things I’m uncertain about, because I often learn a lot in the process about what I do and don’t want.

You’ll learn a lot more from doing than from thinking about doing. Make time for reflection to learn from your experiences, and crack down on doubt. There’s helpful doubt, which shows you what we haven’t considered and strengthens your decisions. There’s unhelpful doubt, which stalls you out and keeps you from making a decision. Know which is which, and keep going!

3. Clean Up Your Mind
It’s critical to learn your mind. Our minds tend to be wild and crazy-making roller coaster rides. Becoming aware of mental and emotional experiences without acting on them is what frees us. Try a form of mindfulness practice: take a few minutes to notice the thoughts in your head and the emotions in your body, without trying to change them or letting them dictate your behavior. You might find this boring or difficult. I promise you it is worth it. You are looking at what is running your life. There is nothing more important than cleaning up what runs your life. It will change the way you interact with yourself, everyone you love and don’t love, and the entire world. It can free you from the tyranny of your own mind.

We tend to have deeply held stories like “Everyone else is better than me” or “I’m better than everyone else”, “I’m inadequate” or “I shouldn’t ask too much from life”. Look at how you act, and guess what beliefs would drive that behavior. I have a habit of wanting people to like me. I’ve looked at that one real hard and found a belief: “I must be adorable to everyone in the world in order to be safe”. Approaches like Immunity to Change are powerful ways to get below the surface; so are practices like Circling, where you get immediate group and interpersonal feedback on how you show up. Try choosing a better story and see how it goes. “I can choose love” and “I can do hard things” are two that have rocked my world. I am happier and a better person when I live by these two stories as inner guides (as opposed to inner autocrats).

Don’t be your own worst enemy, but if you can’t avoid it, learn from it. There’s a neutralizing voice in my head that counters every desire, motivation, or urge that arises, effectively halting any action. I have a very strong inner critic that loves to condemn almost anything. If I believe these voices, I’m done for. I’m miserable. I’m in analysis paralysis, and feel terrible about myself, the word, and everything I do. Through learning the many flavors of my self-handicapping tendencies (basically, listening to the voices in my head without believing them), I can choose something different when they start to get loud: I can choose to validate and support myself, and I can make choices apart from what they say. I can make choices that create a fuller life.

Learn to work with your emotions skillfully. If you aren’t one of the golden children born or raised with this skill, find a modality that suits you and get to work. I use Bio-Emotive, IFS, and a conglomerate of my own self-devised systems along with wisdom from a hundred books and articles to work with my emotions in a healthy way. Basically, learn to feel your emotions without getting overwhelmed by them. It can help to become more aware of the body sensations associated with various emotions. It can help to simply name the emotion you’re feeling. It can help to simply start saying “pain pain pain pain pain” out loud when you’re feeling hurt, to take a page out of Brené Brown’s book (Daring Greatly). If your emotions were a big dog, imagine a future in which you were walking the dog, instead of the dog walking you. This is the goal. Most of us spend our lives avoiding discomfort, reacting to discomfort, and doing anything we can to keep discomfort at bay, including forsaking our deepest dreams and most profound relationships. Be willing to face the beast and free yourself from the chokehold of your thoughts and emotions.

4. Stay Inspired

Listen to people’s stories and learn from them. Find your way towards what inspires you, and then keep it easily accessible. I post notes all over my walls with quotes that lift me up. I keep a notebook where nearly everyday I write down quotes from people who inspire me. Do what works from you. When I’m inspired, I act more like the person I want to be; I’m happier, more loving, and more free. Books change my life on a regular basis, so I keep reading. I subsisted on Peter Senge’s The Fifth Discipline and Dave Graeber’s Debt: The First 5,000 Years (wiki full pdf) for at least a year each. I watch this clip of Jennifer Nettles and pray that I will do something, anything, in my life with the level of mastery and dedication evident in every note she sings.

Keep track of your small wins. It helps to see clearly what progress you are making each day. Make a big, non-virtual calendar and cross off each day that you accomplish something you’re working on.  Check out Adam Grant’s WorkLife podcast episode on Burnout for more on this (NY Times article, podcast episode).

Despair is also powerful. It shows you what you’re yearning for. It shows you what you love. It shows you what is important to you. We only feel despair and sadness because we have experienced something wonderful and significant, which now feels lost. But that feeling itself can be our way home. I was in a relationship with someone whom I love and care for dearly, and we decided to break up because our values were out of sync. When we parted, my reservoir of love for him popped and filled the whole world. I walked through this world of profound love and sadness for weeks. Right within the sadness in his absence was the incredible love from which it emerged.

Feel the sadness and despair fully, and it will break you open to the joy you think you’ve lost. When we become more able to feel sadness and grief, we also become more able to feel joy and love. Practice feeling the full range of emotions, and the energy behind them will become the sea that keeps you afloat, regardless which emotional wave you happen to be surfing in a given moment.

Let disappointment and suffering be the keys to your salvation. Let them breathe your world alive. Feel them fully in your body. Pain can be a different form of inspiration that feels nothing like the classic American happy-go-lucky version, but is nonetheless powerful. It helps you understand every other person in this world who also suffers, who also feels pain and struggles.

5. Keep It Simple

Know where you’re headed. If you don’t know where you’re headed, know what you’re doing right now. Do one thing at once. Thinking about all the other things you have to do just makes you feel busy. Get it all down on paper so you’re not juggling everything in your head, and proceed down your list. Do the next right thing (sometimes Disney gets it right). Doing the next thing is often what reveals the step after it; for some magical, mysterious reason, we generally don’t get to see the whole plan at once, but we can walk it step by step.

Particularly when you have a big task that may feel like too much, break it up into doable chunks or you’ll probably end up putting off the whole thing. Do things bird by bird, as Ann Lamott would say. Make a list of what you need to do, and then go down it, as David Flores Wilson one wisely reminded me when I was feeling particularly overwhelmed. Friends are good for this. Often bigger tasks feel looming until they’re broken down. Rome was built one brick at a time, &c, &c.

Go for quality over quantity. Let one small thing change your whole life. I took four tai chi classes above a wonderful tea shop in Burlington, VT one summer. We learned a practice called “shifting sand”. It is very simple. You stand with your feet a foot apart and shift your weight slowly from one foot to the other. I did that practice on my own for months. It changed the way I relate to my entire body, and helped me relax fundamental patterns of tension in my hips. This one takeaway was immensely impactful, even though I’ve forgotten everything else we “learned”.

6. Build in Structure

It’s insanely helpful to have strong morning and evening routines. Once you have a steady container, you can swap in and out anything that you want to do more of on a daily basis. It will take time to find routines that work for you. Let it. It is worth it. 

My morning routine is something like this: wake up, brush teeth, meditate, exercise, eat breakfast, work. My evening routine is something like this: quick work checkout to reflect on the day, organize desk and books, turn down lights, make tea, brush teeth, get cozy on the couch. Sometimes I’ll read. Recently, my knees have been bothering me, and I’ve started doing PT exercises again. I tack them onto my morning exercise block and my evening routine. Having the structure there already makes it way easier to add things in. I take weekends off from my schedule so it doesn’t start to feel too oppressive. I’ll take random days off when it seems better to do that. However, consistency really does make a difference. If you can’t do the full hour of exercise you planned, at least do 10 minutes. It will help cement the routine even if you just do 5-10 minutes of a practice. If you’re curious about the process of learning from a routine, check out Josh Waitzkin’s The Art of Learning, it’s fantastically inspiring and deliberate.

It’s important to notice what works for you, and what doesn’t. Let the things that work for you guide how you shape your life. For me, having a very clear (and extensive…) ritual for starting work in the morning was very helpful and made me love starting work. I would do a written check-in, read an inspirational note I wrote to myself, and watch a few kickass youtube videos. Planning out what topics I would focus on each day of the week was overboard and made me hate everything and rebel. Forcing myself into a tight schedule that doesn’t align with my natural ebbs and flows is a great way to make myself miserable. Encouraging myself to follow my schedule when I don’t want to helps me stay sane, focused, and grounded. And please–take breaks! If you don’t do it on purpose, you will do it badly and burn out (unless you are totally in touch with your natural rhythms).

Prepare things in advance so it is as easy as possible to make the right choice in the moment (and in moments of weakness). Tape up the snack cabinet, close all your non-essential browser tabs, hide your phone across the room in a drawer, give yourself a pep talk, and begin. Be kind to yourself.

7. Find Your Believers

Let people support you and believe in you, and pick you up when you’re struggling. Find people who are willing to believe your vision is possible, and work with them to make it come true. 

Phone a friend when you’re struggling, or when you’re on the verge of making a bad decision. Let other people hold you accountable. Share yourself with others, make it known what you aspire to, so others can see your beacon and come forth.

8. Be Fearless & Kind

My meditation teacher Soryu Forall tells of a teacher who would sleep with one leg out of the mosquito net to give the bugs something to eat. Two of his students were before him one day, and one of them asked, “Wouldn’t it be kinder to sleep with no net at all?” and the other monk burst out, “He’s compassionate, not stupid!”. Be fearless and kind, but don’t be stupid. Use your discernment, and have courage. It’s okay to get hurt and learn from it, but if you keep getting hurt in the same way, you might have something to do with it. 

Another teacher of mine, Dr. Ellie Drago-Severson, knows this principle well. She is one of the most absurdly welcoming humans I have ever met, and it makes a world of difference. She’s no pushover, either. Often we are afraid to be kind and welcoming because we feel insecure and we are afraid others will take advantage of us. Default to kind, but don’t be a doormat. Remember, win-win or no deal.

Fearlessness comes in many forms. I like to keep in mind that I may die at the end of any day. Really, I could die with any breath, but considering it that way doesn’t tend to support the fullness of my life; it just brings up anxiety. Memento mori, “remember you must die”, is a powerful tool for shattering complacency. Be willing to make use of it. If you were to die at the end of this year, how would you want to live it? What would be most meaningful and significant to you?

9. Let Go

I used to think that “letting go” meant “watching leave”, as if letting go of something meant it would surely cease to exist in my life. It’s more like “letting go of the outcome”, and opening myself to the infinite possibilities that may emerge. I have let go of relationships that I didn’t understand or didn’t like, and they have come back alive and flourishing in a way I couldn’t have planned. I have let go of relationships, and they have transformed in beautiful ways. I have let go of relationships, and they have died out. Letting go is accepting that I don’t know what the outcome will be, but knowing I will do my part (no more and no less) to move towards my dreams. The universe does the rest.

The scary part is that when I let go of something, I have no idea what will happen next.

Many spiritual traditions talk about attachment and renunciation, which is also part of this. We’re generally crazy attached to what we think will make us happy, and we’re often very wrong. We think eating that cake will make us happy, and we’re right for a few minutes, and then wrong for the rest of our lives about that cake. We think this relationship or that relationship will make us happy, and then we find out that they’re imperfect too. Part of letting go is finding a wave to surf that includes the entire ocean, finding a kind of joy that is underneath all of our fixing and doing and becoming. We can practice this with our breath, letting the breath go freely with each exhale, long and comfortably. We can practice this with our minds, noticing when we tense up, and breathing calmly to relax our bodies. Letting go means finding ease, even in dis-ease, and being totally willing to face whatever is happening in this moment.

10. Decide What Kind of World You Want to Live In

David Foster Wallace describes this best in his 2005 Kenyon commencement speech (transcript here). He says, “learning how to think really means learning how to exercise some control over how and what you think. Because if you cannot exercise this kind of choice in adult life, you will be totally hosed.” We have many freedoms in our modern age, but “the really important kind of freedom involves attention and awareness and discipline, and being able truly to care about other people and to sacrifice for them over and over in myriad petty, unsexy ways every day.”

What we choose to focus on becomes our reality. If I focus on food, that becomes my reality. If I focus on my appearance, that becomes my reality. If I focus on what other people think, that becomes my reality. What we focus on balloons to fill our lives. I want to live in the kind of world where people flourish and grow, where people are inspired to pursue their wildest dreams, and where people are wise and loving towards all of life. So every day I ask myself, how will I flourish and grow? How will I pursue my wildest dreams? How will I be wise and loving towards all of life? And then from there, I anchor my attention in my body, and I go forward into the day.

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