Taking creative risks

Nine years ago, I took a huge creative risk. The corporate job I had for a decade ended, and I didn’t look for another one. Instead, I started my own company.

The only problem? I wasn’t quite sure what it would be. What I would do. How I would really earn a living with it.

This was a month before my wife and I had our first son. When we were still living in (a rather dumpy) apartment, saving for a house. A house that no one would give us a mortgage for, because I was starting my own business. Turns out, banks require you to have a steady paycheck in order to give you a mortgage.

Nine years ago this week is when I officially opened the doors to WeGrowMedia and took my first client.

It was the bottom of the recession, and soon after, my wife decided to leave her tenured teaching job to be home with our son.

When I shared this news at the time on my blog, I received this comment:

“Think about your family, you dolt.”

While I didn’t like that comment, I couldn’t help but see their point of view. When many other peoples were seeking financial security in the recession, here we were taking big financial risks. No stable jobs, starting a family, launching an unproven business.

But I can honestly say, these past nine years have been amazing. Full of financial risk? Yep. But also full of deep fulfillment in both my work and personal life.

You see, I work with writers and creators. People for whom risk is a daily action. Where they are exploring who they can be and what they can create. Where they are are sharing their creative work with the world, which is akin to wearing your heart on your sleeve. Doing so almost begs for judgement. “Buy my book,” “Review my book,” “Read my essay,” “Sign up for my newsletter,” “Like my social media post.”

Every day is a new opportunity to create. And a new possibility of rejection.

But would you want it any other way?

Hellen Keller said it this way:

“Life is either a daring adventure or nothing.”

The risk that writers and creators take is the act of living. Of finding out who we are. What we are capable of. Of attempting to forge new connections between people. To bring us to new places, new ideas, and new experiences.

Nine years ago, I set off on this journey with my family. In that time, I have worked with thousands of writers. For each, I have had the privilege of being a tiny part of helping them share their voice, create their work, and connect it to people who care.

Thank you for joining me in this. Your support means so much to me.

How to make serious progress on your creative goals

Yesterday I received a surprising email. It was from someone who I worked with in my mastermind group earlier this year, Karen Lock Kolp. We hadn’t spoken in a couple months, and she wanted to give me an update on the progress she has been making on her creative goals.

But it wasn’t just an email, she shared a video as well:

This is the kind of video that you dream of getting from someone you have worked with. Click above to listen to the whole thing (she gave me permission to share it publicly.)

She shares how our work in the mastermind is paying off in huge ways in her life. She takes me through the specific creative goals she set for herself, and all of the ways she is making serious progress.

But she went further. She talked about how what she learned in the mastermind went on to benefit other areas of her life, such as her health.

If you are considering joining my Creative Shift Mastermind which begins on Monday, but are on the fence, click ‘play’ on the video Karen shared and listen to the ways it has changed her life.

It’s inspiring for me to see what Karen is accomplishing. I was also blown away by her follow-through in taking the initiative to create and share this video update with me.

I talk a lot about how writers should develop a support system of collaborators in order to create momentum to reach their creative goals.

In looking at my family’s budget recently, I was reminded of how that is not just a part of the advice I give to others, but how my family lives. We are always investing in the skills and collaborative experiences that lead to creative growth:

  • My wife takes horseback riding lessons every week. This is a hobby that she started about three years ago, and every time she is on the farm or near a horse, she is totally inspired.
  • My oldest son takes hour-long piano lessons each week, then 2 hours of taekwondo lessons each week, and he just started taking daily violin lessons for the summer.
  • For the past 18 months, I have practiced guitar every day, have worked with one guitar teacher, and am now interviewing local guitar instructors to work with.

This costs us $215 per week for all of these lessons. That is $860 per month.

When I see that number, I think two things: The first is that it’s a staggering number in a monthly budget. It’s easy to feel that all of this is “extra” — expenses that are non-essential.

But the second thing I consider is how this is investment in ourselves:

  • Developing clear skills that will last a lifetime.
  • Creating meaningful experiences every week.

But more than that, what I consider is that each member of our family is growing. Each of us is learning and pursuing something that inspires us.

That feels priceless.

Speaking for myself, I can tell you, there is a profound difference between these two thoughts in my head:

“I always wanted to learn to play guitar, but I just never followed through. I toyed around with it years ago in college… I guess it was just never meant to be.”


“I can’t believe how much progress I have made with the guitar. After decades of dreaming, I’m finally doing. The guitar used to feel like a puzzle I would never figure out. Now I pick it up, and it feels familiar. I’m actually making music that I’ve always felt was inside me.”

For each of these pursuits, they are collaborative. We seek out people to work with, mentors who can help us move ahead.

If you are considering that for your creative goals, consider working directly with me in my Creative Shift Mastermind. When you join the Mastermind, I take you through a step-by-step process to establish rock-solid creative habits, define your creative identity, and get radically clear on your priorities of what to work on and why.


P.S.: You can find Karen (from the video above) online on Instagram, Twitter, and her website.

Give yourself permission to create

All day I talk to writers and creators, digging into how they can create the work they love, share it in a meaningful way, and truly reach people and have an impact on them.

Today, I want to share three core skills that I encourage writers to consider to reach these goals:

  1. Give yourself permission to create.
  2. Treat your writing like an emergency.
  3. Build a community of support.

If these seem like “soft skills,” I can assure you they aren’t. These are the difficult skills that I have found that professional (and semi-professional!) writers and creators obsess over developing. It is hard work, and they attend to it every day.

These are the skills that matter more than analyzing which email newsletter service to use (spoiler alert: they are largely all the same, just pick one), wrestling over whether to try Facebook ads to promote your book (spoiler alert: spend $20 to take out an ad simply to see how it works), or what engages readers on social media (spoiler alert: dogs. Dogs always work.)

Give Yourself Permission

Most writers and creators I know suffer from impostor’s syndrome at some point in their life. Sometimes, they suffer from it on a daily basis.

It’s the voice that says, “Who do you think you are to write?”

Then comes a long list of logical sounding reasons why that person shouldn’t write. This is unique to each of us, but may include:

  • “Only people who have an MFA should write.”
  • “Remember that time you wrote that thing that someone made fun of? Why open yourself up to that again?”
  • “Shouldn’t you be spending this time with your family, instead of selfishly indulging in writing?”
  • “What are you really going to write that is unique? Your ideas are just rehashing what others have already written.”
  • “You are too busy for this. Wait until life slows down.”

The list goes on and on. These are the thoughts that many writers struggle with day in and day out. They are the thoughts that can keep you from writing.

It was only later in life that I realized that my parents gave me an immense gift. They gave me the gift of permission. I grew up encouraged to create. My mom was constantly doing craft and art projects of her own, from cross-stitch to painting, and more. My dad and mom were always running these little side businesses: a stamp business in the 70s and a baseball card business in the 80s.

Again and again, I saw them simply give themselves permission to try something new. Something that required creativity and a little risk. Something that on paper, they weren’t qualified to do. Something that was in addition to their busy day-jobs and other responsibilities.

Because of this, I grew up as the “art kid.” I was always creating something, and my parents allowed me to go to a small local art school starting when I was very young, I think I was 5 when it started, but I’d have to call them to double-check.

I always felt I had permission to create.

Now, years later after having worked worked with thousands of writers and creators, I realize how rare that is. That most people struggle with that first step: allowing themselves to even try working on a creative idea.

While I can’t go back to the 1970s, and carefully encourage you to create day-by-day as my parents did, I can sit here today and simply tell you: you have permission. The only person you need permission from is yourself.

Be generous with yourself. Give yourself that permission to create.

Treat Your Writing Like an Emergency

Stop treating your writing and your creative work like a 3rd rate hobby. Like something that is the lowest of low priorities, that is easily jettisoned from your day at the slightest distraction.

Instead, treat your writing like an emergency. That if you don’t create now… it may never happen. And the your life, and the lives of others will be worse for it.

Extreme? Sure. But let me explain…

I’ve often said, “I don’t believe in balance, I believe in obsession.” What I mean is that most people I know lead extraordinarily busy lives, filled with important responsibilities. They work long hours at a day job. They work hard to care for their family. They have a home to take care of. They need to tend to their own health and the needs of their community.

They try to balance it all.

Yet when I speak to writers who truly write — those who write every day, every week, every month, and every year — they make writing a priority in life.

And they communicate that priority to those around them. It is non-negotiable.

This is a process I have been working recently myself with another creative habit: learning how to play guitar. I’m a year and a half into the process, and each day on my calendar I have four 15-minute appointments: “play guitar.” This adds up to an hour a day. These appointments are mandatory.

This has been the result so far… this is the number of minutes I have practiced guitar each month since I began tracking that data:

I spent 31 hours last month practicing guitar. I can assure you, I “don’t have the time.” Meaning: my life is very busy running my business, working with writers, caring for my family. If someone had asked me a year ago, “Dan, do you have a spare 31 hours this month” I would have laughed and said, “Of course not! Do you know how busy I am?”

Yet, 15 minutes at a time, I have made this creative practice a priority.

I give myself permission. I allow it to become an obsession.

You can take this even further: make it an emergency. This is what I mean: I follow Kevin Smith on Instagram. He’s best known as a writer and filmmaker, but he does many other creative things as well.

For years I have listened to him share stories with a self-deprecating humor.

Then, on February 26, 2018, after performing one show at a theater, and before performing the next one, he had a massive heart attack. He posted this to social media:

He was 47 years old at the time. What happened next?

He changed everything.

Kevin treated it like an emergency. He started a new health regimen. A couple months later he had lost 32 pounds. Then 43. Then more than 50.

In the process, he became a spokesperson for Weight Watchers and posts constant photos of himself hiking and getting healthy.

This makes me consider: how can we make our creative goals feel like an emergency. How can we find the time and energy to create. Do we have to wait for a crisis in order for this to happen, or can we be proactive about it?

Build a Community of Support

I’ve had the pleasure of interviewing illustrator and author Rebecca Green twice on my podcast, and when she shared this insight recently on Instagram, I took a screenshot to save it:

Someone asked her: “Advice to a struggling illustrator in terms of ‘getting there’ successfully?”

Rebecca’s answer: “Build a community of support, other artists, kind people. Make work, share it, it make take some time, but the path is never linear.”

Too many writers and creators work entirely in isolation. As if their creative life is a secret that needs to be hidden from the world.

How did Rebecca develop an audience of more than a quarter million followers on Instagram? I spent hours and hours analyzing it, and the answer I came up with is exactly what Rebecca shared.

She spent years meeting others who create. She did small side collaborations with creators. She shared her work online and off. She showed up to events, workshops, and co-working spaces.

That sounds like a lot of work, right? To get started, I would suggest this: find one person you can talk to about writing or creating.

That’s the start.

One deep conversation. Don’t worry about “followers” on social media. Don’t worry about ROI (return on investment.) Don’t worry if it leads to a review of your book on Amazon.

Just focus on one meaningful conversation around the kind of creative work you love.

Then, do it again. Have another conversation with someone else. That is how you develop a creative community. It’s how you learn to share your own work. It’s how you develop an audience who truly cares about what you create.

If you want help in doing that, or anything I mentioned above, consider joining me in my next Creative Shift Mastermind program which begins July 1. There are only a handful of spots left — join me for three months to establish rock-solid creative habits, define your creative identity, and get radically clear on your priorities. Full info here.


A 90-Day Plan to Reach Your Creative Goals

Heads up: I’m hiring! If you know of anyone who likes graphic design and social media, please have them check out this part-time position. They can work from wherever they live. Details here.

This week, two different writers told me that they wish they had found me 10 years ago. They have been digging into my advice recently on marketing and how to grow their platform, and felt it could have saved them years of work.

The idea of a writer spending years spinning their wheels, frustrated… that makes me sad.

I don’t want to be sad.

So today I want to give you a straightforward 90-day plan to kickstart you reaching your creative goals.

This is the process I have honed in working with hundreds of writers and creators every single day in my private mastermind group. Okay, here is the plan:

  • Get radically clear on your mission. On what you create and why.
  • Pick a clear goal that you can reasonably achieve within three months. It should be important enough to matter, but reasonable enough to be doable in a three-month time period.
  • Have accountability partners. Don’t do this alone. Have people who will hold you to your goal, and can help you along the way. These should not just be faceless people yelling “you can do it!” on social media, but people who are following your progress week-by-week, who feel invested in it.
  • Have a guide, a coach, or a mentor. Someone who will show you a path, but also help personalize it for you, providing you with feedback along the way.
  • Set weekly intentions. Small steps you can take each week that moves you closer to your goal.
  • Assess progress at the end of each week. Measure what worked, what didn’t, and what you learned.
  • Celebrate little successes, and even little failures. All of that is a part of the creative process.
  • Plan for setbacks. For days where you second-guess everything, or are sidetracked by things you can’t plan for like a fender bender, money worries, friends in need, etc.

Want that in a worksheet format? Here is a downloadable PDF:

In truth, it is difficult to do all of this by yourself. To get clarity, to find others to help along the way, to stay on track.

I think that is why I have doubled-down on collaboration over the years. Why I have a standing weekly call with two different colleagues where we help each other through our creative challenges. Why everything I offer requires collaboration — I don’t run any programs where you just get information and are left to struggle on your own. It’s why my days are filled with deep conversations with writers who are busy doing the work.

Because that is what separates dreaming of one’s creative goals, to actually ensuring you reach them.

I genuinely hope the process I outlined above can help you.

But if you find it difficult to find the accountability partners and someone who will give you feedback each day and each week, that is why I developed the Creative Shift Mastermind. For three years, I have spent nearly every single day showing up in this group.

Every day, I:

  1. Read every message from each person in the group, and reply. I see you.
  2. Am constantly amazed at the ways the members of this group support each other.
  3. Guide you through a clear step-by-step program, that is 100% customized to you.

If you want a turnkey solution to making real progress with your creative goals in 90 days, then consider joining the Creative Shift Mastermind. You instantly have me as a guide starting July 1, and I’m with you each day until October. You will be welcomed into a small group of 10-20 writers and creators who are as motivated as you are.

Full details are here. The group is about half-full right now, so if you want to join us, please register as soon as possible.


I Opened the Doors to the Next Session of The Creative Shift Mastermind

For the past three years, I have woken up every day and engaged directly with a small group of writers and creators in my private mastermind group. We dig deep into establishing rock-solid creative habits, defining our creative identity, and getting radically clear on creative priorities. These are some of the amazing people I have had the privilege of working with in the group:

Behind each face is someone with a creative vision, who is navigating a complex life to turn a dream into reality.
In joining the group, they moved a huge step closer to their goal. I’m opening the doors to the next session of my Creative Shift Mastermind, I’d love it if you considered joining me.

It’s a three-month program that begins July 1st.

You work directly with me and a group of 10-20 other writers and creators just like you. We become your support system, brainstorming partners, and the team of collaborators you have always dreamed of.

When you join the Mastermind, I will mentor you through a step-by-step process to establish rock-solid creative habits, define your creative identity, and get radically clear on your priorities of what to work on and why. Whether you are just starting out as a writer or are a seasoned pro, the Creative Shift Mastermind will take you to the next level by providing:

  • Daily mentorship from me.
  • A clear step-by-step program to help you establish clarity and habits for your creative process.
  • Accountability with regular check-ins.
  • Collaboration with like-minded writers and creators.

I’m excited tp spend the summer digging deep into this work. Yes, I know you likely have a vacation planned in this timeframe, so I structured the Mastermind in a way so that you won’t “fall behind” if you are away for a week or two.

This is how the Creative Shift Mastermind works:

  1. When you register you will be given the syllabus so that you have a clear picture of how the entire three month program works. You will also receive a questionnaire from me so that I can immediately begin personalizing things for you.
  2. We use a private shared online workspace that you will be given access to 24/7. You don’t have to show up anywhere at any specific time. The Mastermind is there for you when you need it, and it disappears when you don’t!
  3. Every single weekday I record a brand new video for your group. These videos walk you through the exercises in the Creative Shift program.
  4. You will have your very own channel in the Mastermind where you can share updates, ask me and others questions, and where we show up to support you.
  5. I will provide direct feedback to your questions via text and video. You ask, I reply! I show up to the Mastermind every single day.
  6. Every Monday I post a new topic for that week. I lead you step-by-step through the program. You can spend as little as 1-2 hours per week on the Mastermind, or as much as you like. There is no wrong way to engage with us, and I will share many tips on how you can get the most out of the Mastermind.

The Creative Shift Mastermind is for the writer and creator who is ready to commit to themselves and their work — who wants their work to create an impact in the lives of others. When the Mastermind concludes, you will have a clear sense of what you create, how you create it, and how to connect it to those who will love it.

The Creative Shift Mastermind is like having a personal CREATIVE trainer show up at your door every single day. I’m here in my studio doing this work each day, it would be wonderful to have you join me.

You can find full details about the program here. I keep the group really small, so if you are considering registering, please do so as soon as possible.