The 5 biggest mistakes I’ve made in my business

Feb 3, 2021

I’ve worked for myself for nearly 30-years. I had a straight-job for only a little over a year after college, working at a famous talent agency, and then I started writing screenplays, then publishing books, speaking and teaching, and in 1999, creating online communities and courses.

I’ve had a ton of success and I’ve had far more faceplants and failures. I’ve done so many very dumb things in my business, including refusing to be represented by a leading New York literary agent, all I can do is give myself a hug and say, “You are so adorable and you will do stupid things again and what I love about you is you are always learning.”

In the spirit of learning here are 5 of my biggest mistakes–and yes, it was hard to pick just 5.

1 of 5 | MISTAKE:

Hiring people because someone else recommended them and not vetting with care.

You are the only one who knows what support your business needs – not your mastermind, not your best friend, not your partner, not your social media friends. Interview, call references (yes call! Not email!) and have the person you are considering do a small assignment (paid of course) for you first.

Biggest mistake within my big mistake: hiring someone who told me “I can’t give you any references, my current clients get too freaked out that I will leave them.” Yes, I believed her. Yes, she was a very, very bad hire who cost me thousands.

2 of 5 | MISTAKE:

Over providing and over accommodating.

You love the people you serve and why not bend over backward for them? Isn’t that just good business, underpromise, overdeliver and all that stuff? So your client asks for more revisions than what’s in their contract, you better keep them happy or they might not pay. What’s a little discount between friends? You might not fill the program otherwise. You don’t really want to work with him but hey, it’s moola right?

Investigate your fears behind over providing and over accommodating. Mine are that I think I’m too dumb to be of real help so I’d better throw in more material, more hours, more coaching, and discounts. Yours might be, nobody will like me if I say no, I’ll go broke, who do I think I am to have a boundary?Journal your way to seeing these fears and then make a plan to get help addressing them.

Biggest mistake within my big mistake: I said no to that big-deal literary agent because my editor told me she didn’t want to negotiate with her because she was so tough. In other words, I accommodated my editor over myself!

3 of 5 | MISTAKE:

Cheaping out on business support and learning.

I despise it when someone uses the sales tactic, “If you don’t invest in this, then you don’t believe in yourself.” It’s the worst kind of lie and manipulation.

And there have been plenty of times when I needed to spend more in order to support a project and I cheaped out. I have missed major successes and left money on the table because I was too afraid to take my projects seriously and put money behind them.

Within your current cash flow, what is the best investment you could make to move your most profitable projects forward? Where is the bottleneck? Focus carefully and then spend accordingly.

Biggest mistake within my big mistake: Investing $25,000 in my first business,, and then not hiring even one employee. I put all my money into the best tech and design and then struggled on my own to build it for years.

4 of 5 | MISTAKE:

Spending lavishly.

Repeat after me: there is no magic bullet, no pink singing unicorn, no hidden secret you need to pay 100K to learn.

Yes, coaching, masterminds and courses can be incrementally helpful, but only when supported by a clear need in your business and NEVER out of the hidden hope that someone will teach you THE secret.

Also: don’t go into debt for training or coaching. Please.

Biggest mistake within my big mistake: Hiring a big shot New York PR team at a high monthly retainer to be my managers and find my projects including a TV series. All good until I realized they weren’t delivering results and I took four more months to fire them.

5 of 5 | MISTAKE:

Designing a big thing without sharing it with your people along the way.

We heart-based creative entrepreneurs need to create things that are connected to our hearts, interests and obsessions. Otherwise we won’t stick with the long process of creation and the longer process of marketing.

And we can confuse creating from our hearts with disappearing into our creative caves – creating books, programs, retreats, apps, products – without sharing our ideas with our people along the way to make sure what we are creating resonates and serves them.

Share your ideas and iterate from what resonates. And yes, that means you get to change your mind what you know and teach. There is no Truth with a capital T you are waiting to articulate perfectly.

Biggest mistake within my big mistake: I’ve done this with so many books and programs! I so often hide what I’m doing. But I’m making progress.

Which begs the question: how do we stop making these mistakes? How do you thrive in your business by doing things differently?

I’d love to discuss this!

Join me for a fun interactive Zoom session
on Monday February 8th

at 11 am PT / 12 pm MT / 1 pm CT / 2 pm ET

“How to Fail at Business Without Really Trying: 5 Ways I Blew It — And How You Can Avoid My Mistakes.”

I’ll share some insights, you’ll share some insights, ask questions about your business from me and the group if you wish (we are better together), and get input on your new projects.


Sign up here. It’s free.


Sometimes I get a bit down when I replay my mistakes; from turning down that big-time agent, to losing my email list of 20K contacts, to wasting so many early adopter advantages (first person to talk about self-care in the media! First book on self-care!).

But then I laugh and think of my dad who always said, “Hindsight is 20/20.”

I also know it’s a million times better to have created stuff and put it out in the world than hung back and worried about making mistakes or not doing it right or whatever.

Let’s get together Monday, February 8th (yes the session will be recorded but come live for more fun and to ask questions) and let’s learn together.

Want to get your bother on starting now?

Read the first chapter from my new book for a jolt of fresh perspective and possibility, and a radical reframe on what to do when you are feeling lost, blah, unmotivated, or burned out, in any area of your life or for any reason — even success!

Jettison Self-Doubt and Lose the Itty-Bitty-Shitty Committee and Make Your Thing Now

From the national best-selling author of The Woman’s Comfort Book and Why Bother.

Made for writers, artists, mail art makers, knitters of sock puppets, creative entrepreneurs, photographers, Tarot readers, and anybody who needs to make stuff they love.

I’m not one of those creepy people who make it hard to unsubscribe or email you again nine years after you’ve unsubscribed. Giving me your email is like a coffee date, not a marriage proposal.