The Great Paradox

It’s been a little over a year since I started thinking about becoming a bookkeeper. And now I officially am one. I’m taking action towards my dreams, one baby step at a time, and there is tangible progress. Woo-hoo! Happy dance!


And happy dance for sunsets on the beach!

As with any major undertaking, it hasn’t been easy, and I’ve had to show up, work hard, and ask for it.

I braved the crowded streets of downtown San Francisco to make it to my Quickbooks class twice a week for 5 months, I put in many many volunteer hours at work to learn these new skills and get caught up to speed, and most recently, I faced my fears head-on and took what felt like a huge risk in making my case for an official bookkeeper position with my current employer. And I got it. It became official about a month ago.

I am grateful for this job and the financial security it now brings. Being able to finally add some cash to my savings account along with crucial work experience to my resume, this IS the next best step along my path. Being a planner, a worrier, and an over-analyzer, this stability is a sigh of relief, a big exhale, and comforts me like a warm fuzzy blanket.

So why do I also feel so restless?

It’s the greatest paradox in my life right now: being appreciative of this stability and yet craving change.

I need change. Lest I get stuck in a rut and get bored and/or overwhelmed. Which is the case with city life for me at the moment. After 6 years in SF, I’m done. I long for a slower pace of life that living in a small town provides. What I really want: a small cozy cabin in the woods (preferably with a fireplace and a hot tub!) within walking distance of a grocery store. Quite the change from bustling San Francisco.


I am an introverted homebody who enjoys security and routine, yet I also yearn to explore new places and change up my scenery from time to time.

It doesn’t make any sense and yet this is my truth.

I do what I can now to balance the routine days with the explorative days (whilst working a 40 hour a week office job), but there’s an inner voice telling me there’s more to it. That this isn’t it, the end all, be all. Will I ever be able to satisfy this truth completely and full time? Not sure. Yet. Maybe, maybe not. That’s where the bookkeeping comes in. Because I have to try.

Last month’s official work promotion was a huge confidence booster and bonafide validation that I’m good at what I do and that I’m on the right path. Not only do I seriously love reconciling receipts, but I sense my new skills will open the right doors.

Previous to bookkeeping, I really struggled with finding my niche in my working life. It’s been one hell of a roller coaster with LOTS of trial and error and tears and fears along the way.

In a nutshell, I’ve learned that I’m extremely detail-oriented, and true to my introvert self, prefer the behind-the-scenes kind of work much more than direct customer service or even teaching. And dude, I LOVE invoicing!

Alongside learning where my strengths lie, I also believe that dreams (and dream jobs) evolve. See, there’s that change thing again. Not sure about you, but I know I wasn’t meant to be in any one particular job/career/location all my life. How boring.

At each crossroads in my life, I’ve seen my dream jobs come and go.

Environmental educator, check. Recycling and compost advisor/dumpster diver, check. World backpacker, check. Small-scale farmer, check. Tour reservationist, check. And now bookkeeper, and… check.

What’s wildly different now though, is that becoming a bookkeeper is just part of the evolving dream. It’s not the dream in and of itself, like my past dream jobs used to be. I don’t want to spend years tethered to a cubicle looking at spreadsheets. No way.

What I’m hoping is that having these bookkeeping skills will lead me to the ability to freelance, work remotely, and in essence, make an income from anywhere in the world. Everyone needs a bookkeeper, right?

I live to explore. My wanderlust runs deep in my bones and I want the freedom to travel whenever I’d like, wherever I’d like (be it across the world or across California) AND come home to that cozy cabin in the woods.



How that’ll all manifest remains to be seen. And the dream will likely continue to evolve through the many ups and downs of my journey. But I’m gonna keep showing up, doing the work, and most importantly, take it one step at a time. And oh yeah, believe that it’s possible.

P.S. – Huge appreciation and thanks to Kim of So Many Places for sharing her story, practical advice, and inspiration through her book, Life on Fire, which has provided lots of encouragement along my path. I first read her book a year ago when the chaos in my brain needed some structure and more recently, her blog posts like this one have been resonating with me deeply. 


  1. Beautiful post Sam! So well written and articulately expressed. You have come so far since we first sat on the beach in Akumal and you told me your dream. I think the key is finding joy in ‘what is’ while knowing that it is temporary and that something better and more aligned with what you want is on its way. I wish you a beautiful journey toward your dream life with lots of laughs, tears and lessons along the way xxx

    1. Thank you Sarah! Yes, living in the present moment has been a challenge lately as I keep thinking to “when I…”, but I relish in the joyful moments with friends, family, and doing the things I love. What a journey we’re all on! One step at a time… much peace to you on your own journey my friend!

  2. Oma Less · · Reply

    Again, Sam, a wonderful and thoughtful essay. I am so proud of you—for all the hard work and finally SUCCESS! You come by your skills naturally: I did bookkeeping all through my high school and college summers and my father was a real accountant who taught me! Yes, stability is reassuring and change is exciting and challenging, Keep your dreams alive, but have your feet on the ground
    May you always be happy, healthy and alive. Love, Oma

    1. Thank you for your support and encouragement Oma! Glad you’re enjoying the blog!

  3. Sam! First of all, I love that we were both professional dumpster divers and that we both long for a little cabin in the woods in a small town (with a fireplace and hot tub- totally agree!). I think you are right, that you can do your bookkeeping job remotely from anywhere in the world. You are smart to set yourself up like that. I know it is probably hard for you to see but from this blog post I can tell that you are well on the path to having freedom- freedom to work at a desk, to live in that cabin, or to travel the world. The choice will be yours.

    1. Hey Kim! Yes, dumpster divers unite! I definitely don’t miss those super early mornings checking restaurant food waste though! Yeah, I have no idea how I’m gonna go from having to physically report into an office to a position with remote abilities, but we shall see! Thank you for all the support and encouragement! And for stopping by my blog!

  4. Congrats Sam on setting your goals and achieving them! So excited for you!
    I’m certain you’ll get all you hope for and more. Just keep showing up and trusting that all you want is possible. It is!

    1. Thanks Lauren! Always a process, but taking it one step at a time is key and YES, showing up! Hope you’re doing well and loving all this rain as much as I am!

Leave a comment...

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: