The lessons you need most, learning the hard way, and big dreams: part 1

I’ll be honest,

My face hurts.

It might be from the lack of sleep, or the fact that my face is currently crushed against a table in a coffeeshop, where I’ve inadvertendly placed my head down for a quick snooze, and now I’m covered in drool and blinking rapidly trying to regain a sense of where I am – but no matter.

Actually, now that I shake it, my head hurts, too.

I went to the dentist yesterday and afterwards they gave me 4 advil – I asked for 2 extra – pounding headache, be gone.

… Shit, I’m getting distracted again.


No one told me that start-up life as an intrapreneur and entrepreneur would be this glamorous, this fun. So exciting. Nevermind the pictures and dreams in your mind about making it rich and doing what you’ve always dreamed of doing – I’m sitting in a coffeeshop, sleeping in the middle of the day, boss only to myself — (and lest that sound enticing, let me tell you that being the boss of yourself is hard, taxing, challenging, and at times, disturbing) — try this on for size:

Go home Sarah, you’re working too hard.
You need to finish this project.
But you’re tired.
No one else is doing it.
True – that’s a good point.

In fact, we should make a map of all of these projects.
Sigh. Okay, yes, “we” should … I’ll get on it.

In the same vein, really – everyone’s my boss, I’m working for hundreds of people, the people that are my clients, the job that I am intra-preneuring at and being challenged on a daily basis, the team that didn’t exist yet, except now it does, because we’ve created something new that didn’t exist before. I’m working harder than I ever have, and probably disturbing the nice folks next to me enjoying their leisurely breakfast because, well, I’m snoring. And drooling. Damn it, I’ve dropped crumbs in my keyboard again.  Nice work, Sarah.

“The things worth doing are things that neither you or anyone else have done before. That’s why it’s terrifying. That’s the beauty in uncertainty.” – Jonathan Fields. 

All summer, my friends and advisors have been warning me to take it easy, to do fewer things, to uncheck a few boxes and slow down. I’ve got a hundred projects up in the air, and despite knowing – knowing – that I can’t keep up this pace, I still have the hardest time saying no to things that are in front of me. I couldn’t say no.

But then I had to.

I’m starting a big project – a big, crazy, dream-like project that is at the intersection of my professional interests (landscape architecture and city planning), my business and communication drives (building a website, being a writer, and heading up the communications team at my job), and my desire to form great teams and publish (oh yeah, by the way, I’m founding the organization and publication um, wait. what?).

Ambitious? Yes. More ambitious than I even realized? Certainly. Probably – no, wait – Definitely.

This past month has been – how shall we say it – insane. Working a full-time job and a full-time start-up, while doing a few side projects and occasionally jumping into the Bay – well, it can be hard, although the word “hard” has lost most meaning to me, as I stare stupidly at white walls and try to recalibrate parts of my brain late in the evening. I never use to be a whiskey drinker, and then, now, well baby let me tell you (only sort of kidding). Part of me cringes to write this and share this, because I aspire to the “polished” version of me, the one who thinks she knows what she’s doing – you know, where we all believe that the world is a happy shiny place. I’m not one to shy away from hard work, because I think most of the things worth doing require a little to a lot of elbow grease.

I think most people can and should work harder, actually – because what’s wrong with hard work? – but this feels different.

I’m tired. I’m maxing out. I’m freaking out.

You know, the usual.

And I’ve been absent from this blog – my writing space, my thinking space – a little bit too much.

Trying to do Less.

I wrote an ebook, called Lessons from Less, and even though I sent it out to my friends and peer bloggers, got reviews and feedback, and edited it – I can’t seem to even put it up on this blog, because it turns out the one who needs the advice the most is still me.  It was hanging over my head like a hundred other things, taunting me with finishing it, wanting my attention, and I finally had to say:

Look here, project. I’m putting you on the shelves. I’m going to publish you next. Not simultaneously with this project. Next.

And it seems I need to learn this lesson again and again. Some lessons we learn, we must re-learn. They are life lessons we’re bound to dance with for the rest of our lives; they aren’t something that we check off once and say, well, why, yes – I did that. They sit and wrangle with us, teaching us time and time again to learn and re-learn what we haven’t quite got yet.

I’m still learning. I can’t do everything all at once. Not at the same time. There’s a lesson there – and believe me, I’m learning it.  I will certainly be releasing the e-book at a later date. It just is not the right time.  I just can’t push “send” on something that’s tertiary, peripheral, and not my focus. I can’t send work that’s 90% and not be 100% behind it.

And you know how that feels? Simultaneously awful and wonderful.

Awful, because I had to say no to things that I really still want to do. Three weeks ago, I cancelled my biggest swim of the season, a trans-bay swim I’ve been training to do all summer, a solo 10-mile journey across the San Francisco Bay, because I can’t do it all at once.

I just …. can’t.

Saying that makes me feel miserable, to be honest.

It’s mind-wrenching, numbing, impossible feeling, and part of me feels like I’m letting myself down. There’s nothing quite as deflating as pulling the plug after working so hard. And swimming … swimming is my sanity, my blessing, my space away from life, to sit and be. And yet I had to call it. And say, you know … not right now. Just not right now.  I spent a long morning running aimlessly and ended up down by the bay, watching the water quietly in the early morning, wondering if I was making the right decision, wistful and worried.

Awful, because I’ve now written almost two books, one e-book about lessons I’ve learned, and one book on swimming. I have aims to publish, and I’ve called it quits on each of them. Something’s not right. I can feel it. Not now. And I’ve got to listen to this instinct of mine, despite the angst of having spent so much time working on each of these projects. And saying no to my ambition, listening to my quiet feeling in my gut – it still feels really unsettling.

But what is it that they say in business, in finance? Don’t throw money after sunk costs. In life, it’s the same lesson. Just because you’ve already spent energy on it doesn’t mean you should continue to spend energy on it. And the same with projects, it is with our minds and brains. Free up that brain space. Stop worrying about things that can’t be fixed. Let your mind be free, as they say. Let go.

And then, even though I feel awful – even though this is a bittersweet struggle, a chess play I’ll debate for a bit and reflect, wondering how and what I could have done better – at the same time, I feel wonderful.

Wonderful, because I feel like I can breathe again, slowly, even though insanity is still mounting like a dense fog and I’m threatened to be engulfed in it again. But focused, like I can now focus my energy on two things: my one job, my one project, and then go home and face-plant on the bed every night and get up and do it all over again.

Exciting, isn’t it? Let me tease and entice you with the ways of entrepreneurship next … 

With that said, however, I’m taking a short break here, writing only once per week (more if I can! but I had to insert some sanity parameters into my life recently) and building up some momentum to launch my big project, my crazy thing that I’ve been working on, which started out just by dabbling on the side, which is finally, I-still-can’t-believe-it, nearly ready to go live and I’m in the sidelines, biting my nails and tearing out my hair and then walking out in public, smiling, hiding that fear behind my eyes because frankly,

Frankly, for the record, I have no idea what the heck I’m doing, either. And I’m really glad you’re here with me.

Lessons from the side-hustle-turned-dream-project, part 1:

In the spirit of learning, here are a few tips and notes I’ve jotted down in my notebooks as I’ve gone through this part of the process. It’s unfinished, uncut, more’s coming, but here’s what I got for you:

  1. Not everyone will understand your dreams.
  2. You have chosen a different path than many of your friends.
  3. Put your health first.
  4. If you try to do it all alone, you’re an idiot.
  5. Find good mentors.
  6. Ask questions.
  7. Don’t be afraid of what you don’t know. Sometimes, that’s everything.
  8. Set constraints and parameters.
  9. Have a solid vision plan. A rock-solid vision plan. You’ll need it in the thick of things.
  10. Surround yourself with great people.
  11. Generosity and kindness are always good.
  12. Tact and grace are never inappropriate. Grace under pressure is learned only under pressure.
  13. Choose. Make choices. Cut ruthlessly. Do only the most important thing.
  14. Get sleep whenever possible, and it’s not always possible. Take care of yourself first, as much as possible.
  15. Balance flies out the window, and then sometimes comes back in short stints.

Launching a Project – and a short hiatus.

I’m going to be launching my big research project – a year-long endeavor to study the ins and outs of cities and our urban spaces, particularly the green spaces and the invisible systems that make cities work – and I’m going to post less frequently on this blog for the next month or so: I won’t promise frequent updates, or a return date (although it will definitely be before the end of September).  This is me, trying to take it …. easy?

The project has been more work than I ever dreamed and more fun that I ever could have imagined. The people I work with are incredible. Adjectives fall short. There is brilliance in their capabilities, and I am thrilled, honored, and lucky that they come together to work together with me. Somehow in the span of a year, we’ve assembled over a dozen universities, thirteen people on our team, five editors, and over 40 people featured — we are launching an online journal. There will be six issues of the journal this year, each exploring the ideas of cities, urbanism, landscape architecture, and design.

Why? because where we live – our environmental context – is important to who we are. To me, we are two things: we are what we think, and we are what we surround ourselves with. Once you step outside of your brain, if that’s even possible – looking at the environments that shape our behavior is fascinating. Cities are possibly the most interesting manifestations of being human – they represent how we design systems, how we work together, they hold history in their building walls, and they change daily, yearly, and live beyond any single human life.

A city is analogous to a human body – each with metabolisms and invisible systems and throbbing, vibrant heartbeats. Cities would not exist without people.

And so, in my day job, the one that lets me explore what landscape architecture is and what urban planning is – I’ve taken it upon myself to launch a journal, and issue one is published on September 14th. This Fall, we will be going to the Urban Land Conference, the American Society of Landscape Architects Conference, Green Build, and Blog World, to name a few.

Wish me luck.

If you want to watch what’s happening, check out:, the facebook page, or the twitter page.

To figuring things out, how to start, and how to grow.



12 Responses to The lessons you need most, learning the hard way, and big dreams: part 1

  1. Leslie says:

    Wow. Very ambitious. And very raw and honest. This is awesome. Congratulations on following your dreams, one step at a time. Here in Chile we are building some education/consultancy projects related to intrapreneurship and I’d love to chat with you some time about your experience as an intrapreneur.

    So glad we’re back in touch after all these years!


    • Sarah says:

      Leslie – thanks! It’s been quite a trip, full of ups and downs and no-holds-back insecurities. But making things happen is really quite satisfying. I love writing about it and figuring it out. (Also – I’m so happy that we’ve reconnected after all these years!! We’ll have to catch up about Chile sometime soon!!)

  2. Brandon says:

    Wow, Sarah! I’m intrigued, delighted, and proud all at once. At the risk of sounding cliche, I’m in the same boat right now and things are literally about to take a turn for the even more insane. But it’s all completely amazing!

    Your story is incredibly inspiring, and I hope you will continue to share about how your journey is unfolding here. Actually, we should compare notes sometime. It’s been a minute.

    Keep up the awesome work! And thanks for sharing. :)

    • Sarah says:

      Brandon – I am SO EXCITED FOR YOU! I love watching my friends make things happen and I know how hard you’re working behind the scenes to do everything you’re doing. I’m such a fan of your work and I love that you’re proud of me, too — makes me so happy :) :) hope all is well this week!

  3. Dan says:

    Great post Sarah! Through all of the pain, lack of sleep, whiskey, and saying “no” you are learning, and inspiring others (me) at the same time! You mention that you’re loving every minute of it, which to me is the most important part of life activities. Keep us posted on how everything is going!

    • Sarah says:

      Dan – thank you so much. It means a whole bunch. I took a weekend off and recovered (no whiskey, either! That’s not true “recovery”) — and I’m looking forward to a slightly more sane schedule for a bit. Thanks for the encouragement – it means so much!! Hope you are doing well. :)

  4. […] An entrepreneur is someone who does something. Someone who builds something that hasn’t been built before. A person or business who makes things happen. In a corporate job, a solo journey, or somewhere in between, entrepreneurs and intrapreneurs challenge the status quo. I’ve been fortunate this past year to have several projects at hand to focus on – and while I’ll be analyzing and critiquing this project for a quite a while, here’s a bit more of an inside peak at what I’ve learned and gathered along the way: the lessons from this project, part 2. (For the first post, check out part one). […]

  5. […] you learn away from you. My two lists from launching my publishing venture on landscape urbanism? Part one and part two have 50-odd things I gained along the way. These, I get to […]

  6. […] The lessons you need most, learning the hard way, and big dreams: part 1. Share […]

  7. […] skills and lessons I’ll never forget. For the complete breakdown of post-hoc lessons learned, see “The lessons you need most (part 1)“ and ”20 lessons from launching a project (part […]

  8. […] be received well or picked up by the community. Afterwards, I spent a lot of time reflecting on the successes and failures of a launch and figuring out how to manage my energy […]

  9. Fab says:

    Hi Sarah,

    yestarday I sent you an email ( via the contact form ) about Todd R. Tressider, a very good financial mentor .

    Here are two articles by Todd which might be very useful for your case:


    2) “8th Wealth Building Principle: Apply Leverage To Build Wealth”:

    3) A wonderful principle that if wisely applied can really, really make the difference:

    All the best!!

    Fab,greetings from Italy.