16 Lessons From 16 Years of Self-Employment

Exactly 16 years ago, I celebrated my final day as an employee and my first day as an entrepreneur.

Over the years, my career has gone through several evolutions.

In the Beginning

I started out as a rookie freelance writer, hustling hard to find paying gigs and establish a name for myself.

In the beginning, work was scarce and times were lean. I made temporary sacrifices, some of which I’d recommend (like getting a roommate) and others that I later regretted (like draining all the cash in my retirement account to cover my mortgage).

Little by little, projects came in—a trickle at first, then a steady stream.

Tipping Point

A few years in, a tipping point came, and I found myself with more work than I could handle on my own.

I began scaling—a part-time assistant who later went full-time, new offers that served hundreds of customers instead of one client at a time, then a business partner, and eventually more employees and contractors.

Motherhood and Major Shifts

After the birth of my daughter, things changed.

I wanted fewer demands on my time, more simplicity and quiet. I missed the earlier days of my career, when I worked one-to-one with clients and built close, personal connections with each person.

I no longer wanted to spend my days in team meetings, managing employees, or being responsible for so many people’s paychecks. I was nursing my newborn around the clock, I was tired, and my priorities were shifting. I longed to return to the creative work I loved: writing, editing, and creating beautiful books.

It wasn’t that my professional ambition was dwindling. If anything, becoming a mother made me more ambitious, lighting a fire that hadn’t been present before.

As a new mom, I wanted to level up—become a stronger writer and better service provider, collaborate with the world’s top publishers, increase my income significantly, reduce the number of projects on my plate, and focus on a select few. Do less and do it better. My ambition wasn’t shrinking—it was changing shape.

(I owe great thanks to Dr. Anne Welsh, author of Ambitious Mother, for helping me embrace the shift that was happening inside of my heart and mind, and for reminding me that ambition comes in many forms.)

After some tough conversations with myself and others, I streamlined my career and stepped away from a few endeavors, leaving them in the capable hands of my business partner, who chose to keep the company we co-founded going on her own. (We remain great friends, offering the utmost support for each other’s careers.)

My Work—Today

Today, I get to focus on what I love most:

Writing my books, journals, and card decks with top publishers like Penguin Random House, Hachette, and Chronicle.
Leading a writing retreat in Hawaii once a year, with many guests who return annually.
Working with a small number of clients, helping them land publishing deals and write bestselling, award-winning books that change readers’ lives.

At the moment, my career feels like the ideal shape and size for this season of my life. I’m sure it will evolve again in the future. For now, there’s a feeling of just-right-ness that I appreciate.

My Greatest Lessons

Without further ado, here are 16 lessons from 16 years of self-employment.

None of these lessons are revolutionary, and that is perhaps the point: success in business usually comes down to a few simple, universal, timeless truths—things you’ve heard before, things you’ve even said yourself, but that we all need to be reminded of, time and time again.

Deliver exactly what you said you would.
Hone your skills over time and work toward becoming the top provider in your field.
Keep a record of your wins and the results you get for your clients or customers to remind yourself (and others) why it is a very good move to work with you.
Don’t overinflate your accomplishments, but do state them succinctly and accurately for others to see.
Make the ask.
Take more time away from work—breakthrough ideas arrive during a forest walk, a hot shower, or while laughing with friends, not when you are glued to your screen.
Keep your promises, big and small. Whether you say, “I’ll text you a link to that website I mentioned,” or “I’d be happy to make that introduction for you,” follow through.
It is okay to have high standards and want things to be just right. Surround yourself with colleagues and team members who feel the same way.
Details do matter—font, colors, lighting, timing, tone—because all the details converge to create a particular feeling that clients remember, for better or worse.
Excellence is attainable. Perfection is not.
Define what success means to you personally and commit to this vision.
Be fierce and deliberate about reducing incoming noise. It’s extremely difficult to solve problems and produce your best work when you are bombarded by notifications, distractions, and interruptions.
If your plan is clearly not working, don’t keep doing it harder—pause, come up with fresh ideas, and try again with a different approach.
Put yourself in the client’s shoes: what is their dream? How could you help make their dream come true? What would feel like a miracle for them, provide relief, or make their life so much easier?
Be unexpectedly generous.
When in doubt, the simplest option is usually the best one.

Not everyone wants to be self-employed.

But if this path calls to you, it is a road—much like the journey of becoming a parent—that will compel you to build new skills, increase your ability to tolerate discomfort, and grow in ways you didn’t even know you needed.

To my fellow freelancers, contractors, entrepreneurs, founders, and other self-employed workers: I’m sending solidarity, peace, and power your way.

Thank you for making your contribution to the world, whatever that looks like for you.

PS. One final lesson I want to add: Never miss a sunset.

It’s something my grandfather Selig always used to say, and that my mom tells me often.

Even when you have deadlines weighing heavily on your shoulders, throngs of clients who need your attention, an incalculable number of emails to answer, and loose ends to tie up, don’t lock into your computer screen so intensely that you miss out on your life.

Stop and get a beverage. Put down your phone and look up. Watch the sunset. Take it all in. Savor the beautiful life you are working so hard to build.

No matter how busy or successful you become, never miss those little moments that add up to a life well-lived.

Out of all the lessons I mentioned, this one is the most important, and the one I need to remind myself of the most often.