Starting over with (almost) nothing at 38

Starting over with (almost) nothing at 38

Six years ago I wrote a personal post about the challenges of being a full-time digital nomad, “Starting over with nothing at 32.” Over the years it’s gotten more traction than I expected so I thought it was time for a reprieve. I recently turned 38 (during the winter solstice) and I still have just about nothing to show for my years on earth.

No car, no house, no kids, no retirement fund.

I’m learning this isn’t completely strange for my generation – several of my friends are in similar places.

One of the main differences in my position that changed this year however, is that I now have passive income streams. I struggled over the last two years to switch from client-based income to digital products and courses, and while I’m still figuring things out, I also feel like I’m on the verge of very big things, because:


  • I can now spend most of my time on creative projects that matter
  • I know how to build, design and launch new products (books/courses)
  • I know how to build a large audience quickly for new products
  • I know how to make lead-gen offers that convert, and build traffic with ads
  • I get about 100K visitors a month in organic traffic.
  • I know what type of products people want
  • I know what I want to make


These last two are important. The point of Creativindie is that you can’t just follow your passion, you must have a product that delivers value, and it’s much EASIER to succeed if you make things that matter to an established audience (see a need, fill a need). Be of service. Help others. I’ve done that for the past six years. I’ve helped over 100,000 authors publish their books, directly or indirectly.

“Creating demand is hard. Filling demand is easier. Don’t create a product, then seek someone to sell it to. Find a market – define your customers – then find or develop a product for them.” Tim Ferriss


Word has gotten out, and now I have some brand currency in the form of trust and community goodwill; and I have some organic traffic. I also have different audiences, which means diversified income.

1. My nonfiction platform is mostly authors, but may also include creative people who like to write, or possibly artists, and maybe some freelancers who want to work online or start a freelance business, or become digital nomads and travel full-time. 

2. My fiction audience likes fantasy and science fiction books.

Now that I have some people paying attention, AND I don’t need to spend most of my time on other people’s projects, I can focus on providing my audience with amazing content that I know they’ll love, and I also want to make.

This is one of my favorite images ever. Until today, I thought it was a Golden Age illustration, and it reminded me of early 20th century books like Napoleon Hill’s “Outwitting the Devil.”

I just found out it’s actually a modern artist, but it reminds me of Faust, The Alchemist, Manfred and other stories about learning to face your face – and even command them to assist your quest.

Your challenges, fears and obstacles are not merely things to be overcome; they are stepping stones. Leaping past them increases your momentum and can carry you to new heights.

Speaking of which, now that I’ve successfully “defeated some dragons” I know have more accolades than I had previously: small things I can casually mention that  solidifies my expertise without sounding desperate or braggy.

  • I’ve been featured in CNN for renting a castle for nanowrimo
  • I have a PhD in Literature
  • I’ve sold 50K worth of books on Kindle.
  • I’ve sold more than six-figures of digital products (probably about a quarter-million $, which sounds better… but spread that out over the last decade and it’s not so much).

Those are rookie numbers, so not super impressive, but still far better than average and enough to get a handle on how things work. The really exciting thing is that both of these income funnels are scalable, which means I can 10X traffic with advertising and potential earn 10X the income without doing any extra work.

They’re also cumulative, which means, I can add more products while growing my audience. Each launch will get easier as my fanbase grows.

All this means it should be easier for me to get stuff done and make it succeed the first time. (Here’s a book cover I made years ago… one of hundreds of potential projects I may finish sometime).



If you haven’t read my post yet about the Magician and the Fool, you should check it out.


2018 Goals

Although I’m starting over with “nothing” – I also don’t need to “work”: which means I have 100% of my time. Suddenly, time management is becoming MUCH more important. I can also potentially take much bigger strides now that I know what I’m doing (valuable expertise). This week I made changes to my websites that will probably double my income this month.

So far I’ve been making as much as we need: now I want to make MORE than we need, so I can invest in future security, save up for a nice cabin in Oregon, and give back to the community (by creating more great tools and resources). But I’m not really motivated by financial goals, what I’m excited about is having time for all the projects I’m passionate about, improving my craft, and helping more people with greater reach.

My goals this year:

#1. $10k/month in consistent book sales

I have friends who make much more than this – and I came close at the beginning of last year, but I haven’t published a new book in almost a year and sales are way down. I’ll need about six more books and some marketing to get my visibility up enough… after that I want to publish at least six books a year for the next DECADE or so. 10K a month is the first goal, but once I have multiple series and can invest more in advertising, I expect that number to be double in a few years. I also want a traditional book deal for fiction and maybe non-fiction

#2. $10k/month in passive income

I’m actually getting close to this, and I’m sure I’ll make it once I finish my plan for boosting traffic, conversions and sales. The really exciting thing is, I can spend my time on income-generating tasks – every day to make more money, I can create new content and share it, to get people back to my sites. I don’t have to be “salesy” or pushy, I just need to provide value that’s good enough to share (which means, now that I’m making money with my blog, rather than doing it casually, I’ll up my game and be producing better quality content).

#3. Finish Paid to Create

I have tons of notes and research for a non-fiction book on creativity, and I want to launch it well. It’ll be my first general nonfiction book, but now I have a platform and a lot of peers in the space. I may also start a podcast first to tighten friendships and give influencers a reason to share. 10,000 book sales on launch sounds audacious and a little scary, so that’s my intention. If I can move that many copies the first month, it should be a strong earner, not to mention introduce me to lots of new people. It also means I get to spend more time doing research, which I love (otherwise I wouldn’t have spend 7 years getting my PhD).

I’ll also work on some smaller side-courses for authors and artists, and more tools and templates to help busy entrepreneurs.

#4. Clean up my platform

This is basic stuff I should have been doing already; things like adding thumbnails to my YouTube videos and featured images to all my posts. Basically, instead of throwing up a half-assed note to myself, which I usually do, I’ll spend some time making my content pretty and easy to share. 

I was at a business conference in Vietnam this weekend, and two of the guys at my table were making at least 25K a month with their businesses – they also thought it was ridiculous I wasn’t already making more with the size of my platform and traffic… but I consider myself a creative rebel, not an online marketer, so I’m pretty happy with where I am already.

However, the exchange inspired me to aim higher. By the end of 2018, I’d like to be making 25K/month in mostly passive income. This is enough to keep travelling full-time but also save 75% of our income, and start investing in bigger projects and goals (like buying a castle or at least a creative summer camp for adults).


Travel Plans

A friend got annoyed with me recently when I said we were “kind of sick of travelling.”

I love our lifestyle, and we enjoy our adventures and experience, but there are some important things I feel I’m missing:

  • Friends/community
  • Family/home
  • Pets

We usually spend a few months a year in the USA, but I wouldn’t mind having a more permanent space. I really just want to focus on producing more content by focusing on all the projects I’m excited about, and to do that I need a lifestyle that makes me comfortable and productive – which can be hard to predict or control (last month in Taiwan I did NOTHING; so far this month in Vietnam I feel driven and focused).

In 2017 we started in Medellin, Columbia, then spent most of the fall in Europe (Portugal, Austria, Bulgaria, Scotland).

This year, we’re checking out some of the “digital nomad hotspots” we’ve missed – Saigon now and Bali next.

I’m not sure if we’ll make it to Japan this spring, though Japan is supposedly my “perfect place” (according to astrology) – I’ve always wanted to spend more time there, so we may spend a month in Kyoto. However, there are a bunch of things going on in the USA this summer and we may spend most of May ~ September on the West Coast, before *possibly* returning to Thailand for a big digital nomad conference. Travel is kind of incidental at this point: we need to live somewhere, hopefully somewhere I’ll feel motivated to work on big projects and write more books; hopefully someplace we’ll have lots of friends around; somewhere with great coffee and fast wifi; a view of the beach and/or mountains; animals or pets.


My greatest challenges

Most days I don’t need to drag myself out of bed or summon motivation – I always have lots of enjoyable work to do and appreciate the challenges of writing, especially fiction. If I can work a few hours a day, I’ll be happy – the danger is when I don’t work at all, then feel bad about it, get depressed, eat junk food and stay up all night watching Netflix. I was in a bad cycle in February of 2018, which has luckily passed.

Still, focusing on doing more high-value work that matters requires a bit of diligence and structure.

As St Paul says:

I do not understand what I do. For what I want to do I do not do, but what I hate I do. And if I do what I do not want to do, I agree that the law is good. As it is, it is no longer I myself who do it, but it is sin living in me. For I know that good itself does not dwell in me, that is, in my sinful nature. For I have the desire to do what is good, but I cannot carry it out. For I do not do the good I want to do, but the evil I do not want to do—this I keep on doing. Now if I do what I do not want to do, it is no longer I who do it, but it is sin living in me that does it.

This is pretty similar to Elizabeth Gilbert’s talk about the creative muse; or Steven Pressfield’s “Resistance”  – it’s EASIER to see procrastination as an evil, external force you need to fight against. The danger is blaming yourself or feeling guilty when you’re not as productive as you think you should be (our brain is conditioned towards seeking happiness and comfort, not pushing to create all the time… PLUS high level creative work is emotionally exhausting, and you can easily get burned out).

I tend to work in shifts – a week of productivity, then a week of vegging out and sleeping too much – but my more productive friends rely on consistent, long-term progress. A daily writing habit. 3K/words a day.

I know I’m capable of writing a book in a month, but I haven’t figured out a practical way to keep a consistent writing schedule over the long-term. I want to be Balzac of my age; writing dozens of novels. I’d like to get to 100 books in my lifetime (I’m about 1/10th of the way there). But I’d also like to write great books that have massive appeal and are read by millions, so it’s not necessarily about producing books faster. I’d be happy writing 4 or 5 good books a year.

The challenge is BALANCE – it would be easy to write one book a year and think “I’m pretty awesome”; even if I spend 90% of my time not working. I could also push myself to write 10 books a year (and even if they aren’t very polished, more content will almost always lead to more income).

I don’t want to be “wasting time” not being productive.

I also don’t want to be “wasting time” being productive.

I want my life to be a constant appreciation of good and beautiful things: high quality living = meaningful experiences, slowing down to appreciate.

But I also love the satisfaction that comes from creating value: finishing work and sharing it with the world.

One thing I need to pay attention to is developing willpower: it’s a muscle that can be strengthened and it’s all connected. For example, eating just one cookie or the entire box. Eating more healthy foods or getting exercise. Not only for the long-term health effects, but specifically to make it easier to do what I want to do. Daily habits and rituals could also boost productivity (sitting down to write and setting a timer: an hour a day of writing).


Mostly, I just want to live a life that matters

In two years I’ll be forty. I’m older than the average digital nomad – old enough to be worrying about the future.

Some of my friends have spent the last 20 years paying a mortgage and raising a family. I’ve spent the last 20 years travelling, painting and writing.

On the one hand I have “nothing” to show for the past two decades. Very little savings. No job.

I did get a PhD, but won’t be using it much.


But I’ve been investing in new skills.
Now I know…

  • how to write and publisher bestsellers (that earn money)
  • how to grow an online platform and make passive income
  • how to make videos and online courses
  • how to make things people need and love
  • how to get people to know, like and trust you

In many ways, I’ve been investing in a platform. With a platform, I can focus 100% on my own creative works and have confidence that not only my audience will love them, but that I’ll be reimbursed for the time I invested. That security gives me the peace of mind and enthusiasm necessary to boost productivity and finish the work, without worrying about whether it will be successful.

In many ways, I’m in the fifth step of my six-step plan to creative independence, and beginning to enter the sixth:


  • LUMINOSITY: Filling yourself with passion and joy so that you can give back to the world more than you take from it (luminosity).

I can’t wait to get started.



It’s never too late…

Every day is a chance to start over.

Begin with your decisions and what you want.

Then figure out:

  • What you need to learn
  • The skills or investment required
  • The most meaningful steps you can take

Nearly always, asking for help or favors is not the right way to approach things, because it leaves you with less control.

Invest in your education and knowledge. Yes, it can be difficult and frustrating, especially some of the tech stuff like web design or setting up a mailing list.

Hire someone if you need to. 

Focus on your zone of genius.

Dedicate your focus on becoming the best at what you do.

Make sure you know who your community is and how to serve them.

Don’t compare yourself to others, you are in exactly the right place.

You are precisely who you need to be.

The only important goal is to be a little better today than you were yesterday.

If you choose to, you can achieve anything by making progress every day… no matter how old you are.

If you want more support and friendship, go find it.

If you need more money, provide more value.

Don’t forget to be grateful for what you have.

If you don’t enjoy what you have, it’s never too late to start over.

If you feel stuck, unhappy, uninspired or burdened… be kinder to yourself. 

There is nothing you must do.

Start by chasing your joy. Focus on what fills you with hope and enthusiasm.

If you want to, sell your stuff and move overseas – a fresh start allows you to focus on YOU.

Remember, each breath is a gift.

Hardship and challenge might be opportunities for growth – “the universe never sends more than you can handle.”

When things get tough, “this too shall pass.”

Convince yourself that the universe is conspiring on your behalf, to bring you exactly what your thoughts and actions indicate.

Start with the intention, but make sure you follow through with consistent action.

You can do anything, but you don’t have to do anything. You are awesome. You are enough.

Go out there and make the world a better place (or don’t, and that’s fine too!)


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