A Letter to My Young, Digital Nomad, Freelancing Friend With Big Dreams

5 Big lessons to keep you grounded while you cultivate your dream. Hint: Don’t make your passion project your only money maker.


Kaia Tingley

2 years ago | 5 min read

At this point in my life, the outside world might just judge me to be a spectacular failure. The personification of a lack of authority.

I have gone through my ups and downs. You will have it no different. Failure has different meanings I suppose.

But I love my life. I don’t have to meet the definition of success the outside world tries to give me. I’m very successful in my own ways. Do you hear me? This is written from a position of authority you see.

I’m telling you that the metrics you use to measure success are all wrong. Back up from your myopic gaze upon the numbers and start to look deeper, and tell me what you see.

I’m happy, healthy, have a fabulous marriage, healthy kids, and I get to laugh a lot. It’s not all about the balance in your bank account.

The lessons I have learned from my struggle have been invaluable. After 20 years in the fray, I’m finally starting to really come into my own. I’m not even going to pretend that I’m there yet. And I would not have done it any other way.

Here are some of the things I’ve learned.

Money Can Corrupt What You Love MostDon’t Forget Your Partner While You Pursue Your DreamEvery Idea is Not GoldDon’t Quit Your Paying Work — Not YetDo Less Work Better & Charge More

Money Can Corrupt What You Love Most

I’ve learned that in a world that prioritizes money over people, trying to monetize your dream tends to turn everything you love into one big mess.

I’ve struggled, I’ve dreamed big, I’ve bitten off more than I could possibly chew. I’ve done the grind. I’ve been excited at making small progress, and then, I look in the mirror and realize I have yet to make a fortune doing what I love the most. Writing.

But I’ve made a good life nonetheless. It’s not all about the pursuit of fortune.

Needing money to give the gifts of your heart to the world is untenable. It kills the soul.

Money separates us and divides us and assigns extrinsic value to something that is intrinsically incalculable. It’s difficult to thrive in an environment that kills relationships by relying mostly on transactional models of interpersonal interactions.

TAKEAWAY — Determine your own worth. Don’t base it solely on money. Learn about barter and building tribe.

Don’t Forget Your Partner While You Pursue Your Dream

Another reason I’ve struggled with my own career and my money-making dreams is that I’ve been culturally assigned the tasks of making and running a home. As a woman, it’s the default.

All the very essential jobs that keep your body running — including full-time parenting, cooking, cleaning, laundry, managing the household schedule, budgeting the funds, grocery shopping, transportation, handling nearly all public and private correspondence, holiday, and birthday tracking for all the kids, the adults, and extended family… that job?

Oh, that’s just motherhood.

It’s an unpaid gig. It’s what our society has told women for years that this is what we’re supposed to do prove our worth to the collective. (They’ve also told the equally damaging lie that men are supposed to leave home, work for money, and bring it home to provide for everyone. Whatever happened to being in tribe? This is another article.)

And in this schedule of daily grinds, there is very little room for the pursuit of personal dreams, goals, learning, and making things.

Guys. Pay attention to your ladies. The mamas of your kids. Make sure they are doing ok. There’s a lot so many of you take for granted. See how you can lighten her load a little. Suss out the workload and carry more of it. We are sick to death of being the default on all of these things.

TAKEAWAY — Grow up and get your hands in the dirt of life. Pay attention to your partners and your kids. They will nurture you.

Every Idea is Not Gold

Not everything you think of will be brilliant. The market might not be ready to receive what you have to offer. You may not know the way to connect your solution to other people’s problems in real life, because you haven’t lived those problems yet.

You are still fresh. New.

You haven’t taken enough training sessions with the Pain Teacher yet, and you don’t know what it is to be other people and to suffer. Not yet.

You go through a lot of bad ideas when you are learning. It's the human condition. To wonder whether or not we are truly… good enough. To feel worthy of love and belonging, as Brené Brown has said.

TAKEAWAY — Be patient. With yourself and with others. Take time to ripen. Take time to breathe. Calm your triggers. Ground yourself, sons, and daughters. Tap your roots deep.

Don’t Quit Your Paying Work — Not Yet

If you make your passion project need to earn money to be considered of value, and therefore worthy of creating, it will corrupt the process.

The value of your gift, your passion project, to the world will be based on relationship, not on transaction. Money and value and worth can take on a fundamentally different framework. If we ultimately want to, we can choose to change how the money system works. Money is just an agreement.

A lot of this is happening in the barter economy & within local communities. Local groups are loosely affiliated and mutually symbiotic. The woodworker, the martial arts teacher, the Chinese medical bodyworker, the moms that organize the school pods in the time of Covid 2020, we all work together.

Try a subscription model or a patreon. Ask your people for the support that you need. Watch Amanda Palmer’s amazing TED talk on the Art of Asking. Productize your learned wisdom and share it back to the world. Live the life you want and teach others what you learn along the way.

TAKEAWAY — Trust that you will be supported by your community.

Do Less Work Better & Charge More

Get really really good at doing great work in an in-demand skillset right now.

Calling all podcast editors, video editors, conscious people that want to make a little bit of money working in the digital tech realm and helping other visionaries achieve their self-actualization as we all work to heal the world….


Yeah. You.

Come bill the creators a livable wage to edit our videos for us We will pay you for this. Serve the collective cause. Help us change the narrative. Help us change the stories we teach to our children.

Work one week out of the month and book clients out in advance. Work X number of hours to meet your financial needs, and spend the other three weeks of the month on your passion project. This will make developing the gifts of your heart… fully self-funded. And that is priceless beyond measure.

TAKEAWAY — Work smart. Not hard.

An Old Poem to Inspire Your Journey

We are the weavers
We are the woven ones
We are the dreamers
We are the dream
We are the flow
We are the ebb
We are the weavers
We are the web

TAKEAWAY — Blessed Samhain y’all. Hell of a year. Stay strong. Breathe. Dance and Laugh as much as you can. Don’t be afraid.

Thank you to the inspiring young man I talked to this afternoon. We had a lovely chat about things and I write this, a kid of Letter from an Elder to the young of our tribe. His website is killer btw. I’m trying to get him to come back to Medium and write here.

Peace out y’all Have a beautiful day.


Created by

Kaia Tingley







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