The Obstacle is the Way

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Peter and I listen to The Tim Ferriss Show every week. As a result, we are richer intellectually, physically and spiritually. The only way we aren’t richer is financially, since we’re suckers for the books Tim recommends. We figure it’s a worthwhile trade off.

The Obstacle is the Way by Ryan Holiday is one such recommendation: arriving on our doorstep mere days after it was mentioned on the podcast (Marry me, Amazon Prime!).

The book is based around the Roman philosophy of stoicism. Stoicism is something that is practiced by those who would prefer to maintain calmness in the face of frustration.

The philosopher and writer Nassim Nicholas Taleb describes a Stoic as someone who “transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.”

Um, yeah, okay – sign me up for that. Sounds very zen.

In all seriousness, as someone who has actively avoided anything with “philosophy” in the description, I was surprised at how inspiring I found this book. Holiday does an excellent job breaking down Stoic philosophers’ ideas into modern day advice. (And I freaking LOVE modern day advice.)

Here’s some key takeaways for me. About half of these are now personal mantras. (I told you it was a good book!)

Loving your fate

A key idea, reinforced frequently throughout the book, is “amor fati” – love your fate. Anything that happens around you, or to you, must not only be okay with you, but be the best thing that could have happened.

Holiday writes, “No-one is talking glass half full platitudes here. This must be a complete flip. Seeing through the negative, past its underside, and into its corollary: the positive.”

This isn’t an excuse not to reach your goals, to love your fate no matter what and not reach for more. No – Holiday argues that by loving your fate (the things you can’t control) you can more easily navigate past the obstacles towards your goals, with a clear head and happy heart. Loving the journey without being attached to any one route.

“Think water. When dammed by a man-made obstacle, it does not simply sit stagnant. Instead its energy is stored and deployed, fueling the power plants that run entire cities.”

Becoming Immune to External Stressors and Limitations

We’ve all met someone (or in my case, live with someone) who never seems ruffled, concerned, or angry. When faced with adversity, they break down the tasks in front of them into pieces and calmly get back  to business.

Isn’t that annoying?

Holiday says that advantage is available for each of us to gain. We can all be that calm person unfazed by traffic, a bad boss, a stolen laptop, a missed opportunity.

He writes of Stoicism: “It’s a power that drives our opponents and competitors nuts. They think we’re toying with them. It’s maddening – like we aren’t even trying, like we’ve tuned out the world. Like we’re immune to external stressors and limitations on the march toward our goals. Because we are.”

Embracing Crisis

Holiday quotes Obama’s advisor, Rahm Emanuel, “You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term, are now immediate and must be dealt with. A crisis provides the opportunity for us to do things that you could not do before.”

Loving the crisis (loving your fate) is the way to embrace the stress, use it to your advantage, to push past barriers, and get stuff done.

(Which explains why writing a college essay the night before it’s due is always so much easier…)

Enjoying the process

Stoicism encourages us to “Think progress, not perfection”, to break down obstacles in front of us into small pieces.

“And when you really get it right, even the hardest things become manageable. Because the process is relaxing. Under its influence, we needn’t panic. Even mammoth tasks become just a series of component parts.”

 

 

Expecting and preparing for tough times

The only thing we can change is ourselves. The world isn’t going to get easier to live in, work won’t magically become less stressful. Holiday explains, “You’ll have far better luck toughening yourself up than you ever will trying to take the teeth out of a world that is – at best – indifferent to your existence.”

Holiday pushes us to not only like (or love) tough times – but to expect and prepare for them.

I especially love this section:

“Are you okay being alone? Are you strong enough to go a few more rounds if it comes to that? Are you comfortable with challenges? Does uncertainty bother you? How does pressure feel? Because these things will happen to you. No one knows when or how but their appearance is certain. And life will demand an answer. You chose this for yourself, a life of doing things. Now you better be prepared for what it entails.”

^(Repeat to yourself each morning while brushing your teeth).

Flipping the obstacles

Winston Churchill had an acronym he would return to frequently: KBO. Keep Buggering On. (This will probably be my future tattoo).

Loving tough times, expecting tough times, and then pushing through tough times relentlessly takes a special kind of strength.

Holiday says the only way to gain this strength is to practice by doing, building mental muscle.

“Passing one obstacle simply says you’re worthy of more. The world seems to keep throwing them at you once it knows you can take it. Which is good, because we get better with every attempt. Simply flipping the obstacles that life throws at you by improving in spite of them, because of them. And therefore no longer afraid. But excited, cheerful, and eagerly anticipating the next round.”

 

It’s not about you

These are all inner tactics and techniques to steal your mind. But sometimes the best way to get out of your own suffering, to get out of your own head and love the struggle, is to think about others.

Holiday encourages us all to step out of our selfish struggles and to understand that someday we will die. Our individual legacy is small. But we have the opportunity to be part of a greater whole, feeling the same feelings, and experiencing the same struggle.

“Embrace this power, this sense of being part of a large whole. It is an exhilarating thought. Let it envelop you. We’re all just humans, doing the best we can. We’re all just trying to survive, and in the process, inch the world forward a little bit. Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger.”

The Stoic Mantra

See things for what they are

Do what we can.

Endure and bear what we must.

What blocked the path now is a path.

What once impeded action advances action.

The Obstacle is the Way.

 

 

Muscle Memory

I just completed AltMBA – a crazy, interesting, and, ultimately, transformative experience I’ll probably write about later.

Notable in and of itself is that the program requires students to write and published three researched, thoughtful blog posts every week.

Now that it’s over (it’s been over since Monday), I kind of miss writing that frequently. I would not normally choose to start writing after a busy day at work – but I did it anyways. It was required, and I did the work.

I’m hoping the muscle memory of writing frequently continues in this space post AltMBA.

There’s something about showing up to write day in and day out that’s really inspiring. I mostly turned out mediocre writing – until an idea would appears that I’d never even heard myself think before.

It’s pretty cool – and I hope to keep doing it here.

 

 

Thoughts + Observations

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A few things I’ve been thinking and noticing lately:

  • I am very momentum driven. Working a lot = I like working. Taking a break from routine and having a sporadic schedule (i.e. holidays) is like climbing into a warm bath I don’t want to get out of. It’s hard for me to jump into the rushing river of work – but once I’m in the water’s fine. Reminding myself this as I gear up to get back to the office tomorrow.
  • Sleep is my single biggest influencer. Not a big surprise, I’ve always known this, but getting enough sleep over the holidays has reminded me that I am a different (much better) person when well rested.
  • My self-deprecating humor is probably enforcing some habits I don’t love about myself. Example: I’ll riff on the fact that that I hate summer and sunshine, or that I’m bad at directions. True as these statements may be for me now, saying them out loud over and over is likely subconsciously preventing me from taking steps to change.
  • Tuna salad on greens (with Mama Lil’s peppers) has been my favorite lunch for weeks and is still going strong.
  • I’ve been reading a lot of non-fiction (for AltMBA, rapidly approaching). Feeling ready for fiction. Next up may be my yearly or so re-read of the Harry Potter series.

Also worth noting – the ever amazing Peter has put together a cool project called A New Year’s Reader. Worth a thoughtful read (or two).

On Recognition

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Home for the holidays.

My dad was a bigtime hockey player growing up and in college. He’s owned this trophy shelf since before I was born. My brother and sister and I used to love to play with the various cups and medals and trophies.

As we started to win our own trophies growing up, my dad made space for us on the bottom shelves to display our awards.

I wasn’t a particularly athletic little kid under the age of ten. My brother and sister received soccer trophies each year at the end of year pizza parties. I remember feeling a little sad not have anything to put on the shelf. My only athletic pursuit was riding horses, and I didn’t compete in shows. I just liked horses.

My parents once bought me a horseback riding trophy from the trophy store so I could have something to put on the shelf.

As I got older, I  began competitive sports and entering contests. I’ve now won my fair share of ribbons and medals and trophies for the shelf (Pseudo-awards like Most Inspirational and Most Improved? Got em both). My parents still keep the shelf displayed upstairs in our house, old high school awards getting a bit dusty.

Though I guess I liked the trophies, I’ve always been more about verbal affirmations. Whatever feedback my coach would give me after a race mattered so much more than the ribbon I’d be mailed after the fact. How much feedback I got from my teacher on an award was far more important than the prize or certificate.

Just a big metaphor for what we know already: salaries and bonuses are great, but we often all we really want is recognition from the people we work with. Do we matter? Are we making a difference? Are we doing good work? Are we uniquely important?

These are the trophies we really want.

Tis The Season

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Tis the season for Pumpkin Spice Peanut Butter and rainy weekends spent at Costco sampling. It’s dark at 5:30pm and cold enough for a jacket.

I realized lately that I am really proud to be myself in this season of my life right now. I’ve been challenged every day but I am experiencing the best kinds of challenges. There is very little emotional turmoil and just a lot of external company stuff coming my way. It’s mentally taxing but totally fun. I’m not wrestling with personal stress or family/health problems or any kind of major life changes. Just a lot of new professional challenges, which I love dealing with because every step is an opportunity to learn and grow my abilities.

When I am faced with these kinds of professional challenges, I love to get outside my brain and listen to podcasts. Though I listen to podcasts daily regardless of my stress levels, when I am in an exceptional state of exhaustion or overwhelm, it is like I am uniquely primed for some kind of breakthrough. At these moments, my protective and naturally cynical layers are thin and something someone says on a podcast can really hit me just right. Once an idea or a thought is in my head like that, it can shake around in my brain for weeks.

This happened recently on an episode of The Tim Ferris Podcast interviewing Youtuber Casey Neistat. He emphasized how hard and yet worthwhile it is to practice being a positive-minded person. I’ve always felt that way personally, but hearing him say it out loud made it feel like a challenge I could respond and step up to. I’ve been thinking about action steps to keep negativity out of my mind and out of my reactions.

It’s an exciting stage we are entering at Wild Friends and I feel like doors are opening everywhere we look. Very exciting for Wild Friends and so fulfilling for me after four years of trying to figure out what is even going on in this crazy business world. I am still completely confused at the bottom of a tall mountain but at least I am slowly figuring out which way is up.

Forgetting

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I’ve heard it said about Ironman triathlons and childbirth and lots of other (extremely) uncomfortable things: it hurts very badly while it’s happening, and it’s very, very hard, but somehow the power of the human brain makes you forget.

Apparently (I say apparently because I haven’t done either of these two things) you look back and all you see is crossing the finish line or your brand new baby – the hours of pain and struggle somehow faded away into a distant corner of memory.

There’s a parallel, I think (I hope) in this business of building a business. I find that my memories of the struggle in the early days of farmers markets and street fairs are fading even now into a blend of relaxed fun that I look back on now and think “simple times”.

Of course, this isn’t true. There was, for example, the time in late August 2011, when I sat sobbing on my friend Lily’s back stoop, on the phone with my dad, as I realized sadly and suddenly that I really had no idea what a “valuation” was, with only a matter of days left until we were to be filmed for national television to entertain the american public by arguing about – among other things – our valuation.

Shortly thereafter, there were the lonely months spent living in my parent’s house, back after just two short years of college liberation, with 10,000 jars of peanut butter in the garage, one equally homebound co-founder, our shared and borrowed car, and hours upon hours of time. We spent most of this time sampling our products in stores, staying until the very last potential customer (potential customer = human being) had pushed the very last grocery cart into a darkening parking lot, and disappeared.

Perhaps most dark of all were the months after getting served on the basis of our company name trademark – attempting to fight back, then conceding, then wrapping our minds around a company name change. Conflict abounding – coming to a head in frequent, contentious meetings at the local Starbucks. One barista saw Erika and I meeting with my parents there so much, often under such duress, that she thought we were the subject of some suburban parental intervention.

“Simple times” these were not. Each month of Wild Friends has been a miniature dramatic performance of ups and downs, each day ending with a hand to the forehead and a cry of “so much going on!”.

It is probably good that I don’t always remember all of this minute detail – that each day of struggle somehow feels fresh and new and I face them as if each stage prior was easier, just a warm-up for what is happening now. I really need all the optimism that I can get.

And yet the pain of forgetting on almost a daily basis that running a business is really hard, and remembering again the next day, over and over – that’s the part that can really suck.

Enough “Crazy” Talk

Each week, I get a phone call from our external accounting contractor. (This is essentially a fancy way of saying that I am finally paying someone smarter than me to manage our Quickbooks so I can quit messing it up).

The woman I speak with each week is amazing – great at her job, good sense of humor, and generally makes my life much easier. So, when we start our phone calls, I like to be considerate, ask her how she’s doing and engage in a bit of small talk.

This morning’s small talk started like this:
Me: “Hi, how’s it going?:”
Her: “Great, how are you?”
Me: “Good – happy it’s Friday! It’s been a crazy week.”
Her: “Wow, it seems like it’s always a crazy week for you guys.”

At this point, I immediately felt sheepish and felt like backpedaling. Now that she’d mentioned it, I realized how on pretty much every weekly call that’s the phrasing I use:

“Crazy.”

Sure, every week at WF is eventful, but not truly crazy. I’m not any busier than anybody else with a modern job. Besides, I really don’t want to be the person walking around complain-bragging about how “crazy” my week is or how “busy” I am.

If you say it enough, it becomes true. And I’d hate for a key descriptor of my life to be “crazy”.

How to Eat a Whale

I read a NY Times piece this morning on Jim Dolce, the CEO of Lookout, a mobile security company. He had an excellent quote on managing lots of things at once — a necessity when running a fast-growing company.

You can’t get things to change as fast as you would like them to change. You can’t work serially; you have to work in parallel. You have to attempt to work multiple changes at the same time and then, over time, you’ll begin to see the results, and things will begin to converge.

When you’re impatient, you attempt to get something done so that you can then, in serial fashion, go to the next thing. Instead, you have to go wide and work multiple issues at the same time and be patient on each of them. Sooner or later, they will converge.

This reminded me of a more simplified version of this idea, from one of my favorite authors.

MELINDA MAE
by Shel Silverstein
Have you heard of tiny Melinda Mae,
Who ate a monstrous whale?
She thought she could,
She said she would,
So she started in right at the tail.
And everyone said, “You’re much too small,”
But that didn’t bother Melinda at all.
She took little bites and she chewed very slow,
Just like a good girl should…
…And in eighty-nine years she ate that whale
Because she said she would!

Both excellent reminders that to eat a whale, you have to take lots of tiny bites.

Book Report: The Girls Guide to Hunting and Fishing

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I read this book in one sitting while getting my hair cut.

Is that really strange and anti-social? I like to think it’s a relief for the hairdresser when I bring a book – she doesn’t have to ask me what I do for work or what I’m doing this weekend or what celebrity I wish I could trade hair with. I’m just reading. She’s trimming and blow drying. We’re coexisting. Either way, a book sure beats flipping through US magazine and small-talking for an hour or two.

The fact that I read this book in one sitting means two things:

  1. This book was really good
  2. I am now awash with emotions

I love reading a really good book in one sitting because the rapid overload of experience fills me with BIG BIG FEELINGS. I am currently steeped in deep personal thoughts (and, as an important aside, my hair looks really good).

The Girls Guide to Hunting and Fishing is a fiction novel that reads in sections, following different phases of the protagonist Jane’s life. Starting adolescence and traveling through adulthood, we follow Jane through different jobs and romances, in a series of vignettes. Ultimately, though the book is more tuned into her inner life than relationships and careers — a refreshingly funny, touching and meandering, yet not plotless, exploration of growing up.

I often feel that good books come to me at the perfect time. This novel brought questions already hovering in the back of my mind to the forefront. I can tell that I’ll be thinking about The Girls Guide to Hunting and Fishing for a while (or at least until my next haircut).