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Posted by in Tulum | 9 comments

Cesiak sunset

We can’t believe we’re saying this, but our leap year is almost over. Or is it?

This sunset is over a lagoon in Sian Ka’an, which we took yesterday since we’re back in Tulum. (That’s a story for another day.) In just two weeks, we’ll be driving across the US-Mexico border. After visiting friends and family throughout California, we’ll hike all 165 miles of the Tahoe Rim Trail with my dad. Even though it won’t be abroad, it will be the grand finale of our year.

We’re so, so glad we took this year. Transformative is the word I’d use. Not only did we see beautiful places, but it has strengthened our relationship, our skills, and our ability to adapt. Just as important, it has reinforced our desire to live by our definition of success — not someone else’s. So, with that, we announce our next leap into the unknown: our new life as digital nomads.

/ What do you mean? / To us, it means a life focused on strong relationships and new experiences. We’re cutting out the things that don’t matter to us — an endless race up the career ladder, square footage with fancy furniture, the latest fashions and gadgets — to focus on the things that do: spending time with people we care about, jobs that challenge and provide meaning, and making the most of our time on earth.

/ OK, but what does that mean? / Chris and I have found a way to structure our lives to be location-independent. We are both embarking on location-independent careers, which provide us with fun challenges and income. While we won’t necessarily be abroad — there are lots of places to see in the US, too — we’ll be exploring different towns, cities, countries as well as making our way to visit friends and family more often than in this past year. So we’ll be nomads, and we’ll work digitally. Get it?

/ How did you make this decision? / It all started when we asked ourselves, “You know, we could pretty much live anywhere after this. Where should we go?” And we were stumped. Not because we couldn’t think of a place, but because we thought of too many places. Why limit ourselves? So we put together a budget for this new life, scheduled a meeting with our financial planner, and started making life decisions with this plan in mind.

/ Where will you live? / We’re keeping our condo in San Francisco, both as an investment and because we may want to move back one day, but for now we’ll continue renting it out. Maybe we’ll spend a month in Boulder, then two months in Tulum, then a month in Santa Barbara and San Luis Obispo before heading to Florence for two months. You get the picture. If it’s got internet access, it’s fair game. We’ll continue to rent Airbnbs/short-term apartments. The good thing about Airbnbs is we get double credit card points which means free fliiiiights…

/ Won’t you miss your friends and family? / Of course! But with this new setup, we’ll actually see more of our friends and family because we’ll have more flexibility. In our pre-leap-year life, we were limited to whirlwind weekend visits or setting dinner dates a month in a half in advance. The real question is whether our friends and family will have time to see more of us!

/ What will Chris do for work? / Even before we set out on our leap year, Chris started investigating location-independent careers. He did a month-long internship to learn search-engine optimization, which, in April, turned into a paid role with an SEO agency called NoHatMedia. What does he do? Let’s say you own a business and you want to show up as the #1 Google search result when someone Googles “plumber in Walnut Creek,” “video production crew in New York,” or “best hotel in Tulum.” Chris helps make that happen. In addition, he’s built a network of websites that generate side revenue through advertising.

/ What will Tamara do for work? / I plan to return to my former profession, but with a twist. I’m setting out on my own as an independent consultant, providing communications support to do-gooder organizations. While I’ll take on my own projects, I’ve also joined the network of consultants at wonder: strategies for good, spearheaded by my friend and former Fenton colleague Robert Pérez. As a result, I’ve been working on projects to advance LGBT rights and give second chances to ex-offenders even while on the road. In addition to consulting, Awesome Supervisory Skills continues to be a source of income and an exciting project to promote. And I’m in the process of developing a set of coaching offerings around career mentoring and traveling sabbaticals. I already have my first coaching client!

/ How much will you work? / As much as we want. The beauty of living the 1099 life is you can take on as much or as little as you need. The downside, of course, is not having a predictable income. But to us, the flexibility is worth the unpredictability. We’ve had days where we’ve worked all morning, then hit the beach all afternoon to read. We’ve had days where we’ve been so deep into a project that we worked 10 hours straight. And we’ve had days where we haven’t worked at all. It’s about working smarter, not harder.

/ How does Holly feel about all of this? / I’d be lying if I said I haven’t worried about Holly. It’s not the traveling, it’s her age — she’ll be 16 in December, and that’s tough for a dog no matter where she is. While she’s showing some signs of slowing down, she’s still a happy dog with lots of energy. Chris always says, “As long as there are treats to be eaten, this girl has plenty of reason to live.” That said, we’re going to cool it with the border hopping/long-distance air travel to cut down on vet visits…and save me from the painful bureaucracy involved. We’ve made a lot of decisions with this girl in mind, and we’ll continue to do so.

/ Do you hate responsibility? When will you get a real job? / I’d hope no one we know would ever think this, but just in case, here goes: it takes a lot of discipline, maturity and, yes, responsibility to know what you want, set a goal, and take action to achieve it. Believe us, it would be a lot easier to slip back into our old lives because we already know how to do that. But what does that get us but stress and regret? It certainly wouldn’t serve some higher purpose. And, as time has shown, there is no such thing as a “safe” job. I’m proud that we’re adapting to the new world of work, and it will be an exciting new challenge to be self-employed.

/ What about health insurance? What about your stuff? / Like other self-employed people, we’ll buy our own health insurance. It will be an interesting challenge to figure out how to not double up on coverage while we’re abroad. In terms of our stuff, we have some things in our basement in San Francisco that we didn’t have time to sell before we left, so we’ll probably get rid of more. Maybe we’ll just keep our camping equipment, different seasonal clothes, and some important keepsakes there. Otherwise, we’ll continue to live out of our backpacks. We haven’t wanted for anything!

/ This sounds too good to be true. What’s the catch? / If there is one, I’m sure we’ll come across it eventually. I’ve already mentioned the potential downsides to self-employment. Honestly the only thing that comes to mind is when we end up in a less-than-ideal rental. But we’ve got lots more experience now and know how to spot the red flags.

/ How long will you be on the move? / As long as we can and want to, we suppose. Maybe we’ll fall in love with a small town we visit and decide to stay. Maybe we’ll miss San Francisco and go back to our condo. Maybe we’ll turn a minivan into an RV and drive through all of the Americas. That’s the beauty of it all: the possibilities are endless.

/ Aren’t you scared? / Yes. But you know what else was scary? Knowing exactly what every day was going to look like. The same commute, the same routine, living for the weekend instead of living. It is very likely that we could fail at this. Or, we could get sick of it and decide we want to settle down someplace sooner rather than later. Any number of things could happen, and it’s not worth putting the brakes on just because of the worst-case scenario. That’s like saying, “Don’t drive to the store — you could die.” So instead, we’ll close with a wise quote:

A ship is safe in harbor, but that’s not what ships are for.

Thanks for sticking with us until the end and for the encouragement and support. We’ll continue to share the tail end of our adventures, as well as other reflections on the year.


Holly the traveler

Holly, looking forward to her next adventure




  1. Congratulations on unearthing a way to live by what will make you happy! You cannot ask for a greater gift in life.

    Hope you’ll still keep posting adventures and updates on your blog!


    • Thanks, John, for the encouragement and positive thoughts! xoxo

  2. If you ever come through Dallas, Sharmila and I would love to host you guys and catch up on your digital nomad lifestyle.

    • Awesome! Thanks, Jas and Sharmila! :) We’ll have to have some of that Texas BBQ.

  3. Ahhhh I’m so excited for you guys!!! I just had din with a couple who hop from house sitting gig to house sitting gig and have location independent careers. Great way to see cool places and also love affordably. Let me know if you want to connect with them!

  4. Congratulations you two for knowing what’s important and what makes you happy in life!!!

    “And as time has shown, there is no such thing as a safe job…” You’re absolutely right! I was so depressed yesterday to get a call from a coworker to tell me that she showed up for work in the morning only to be told that her position has been eliminated. Just like that! She’s been with the company for nearly 20 years. Shows up to work on time everyday, a hard worker, with great mind and experience under her belt. Offered her a position somewhere within the company that’s not within her alley but she had until 4:00 pm yesterday to make a decision. It’s like a slap on the face for all her hard work and dedication. SAD…..

    I’ll be seeing you soon and can’t wait!

    • Thanks, Mommy! See you soon. Love you.

  5. Sometime when you are in LA PAZ, travel north to our little village of san felipe! you may not leave…lol and, you are ALWAYS welcome here in walnut grove (northern calif) and spend some time on the Sac River. we are gearing up for our cruise to the Baltic Sea-leave here for 6 weeks on aug 25. hope to see you SOON! Oh, and almost forgot….bring your dad with you!!!!

    • Sounds good, Bill and Kathy! We’ll let you know when we’re coming to visit. :)

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