As I’ve been taking some time to plan for the new year, I decided to revisit the Creative Retreat Guide for Business Owners that I created a few years ago.  I based it on questions I asked myself as I reassessed my own business during a time of upheaval, as well as those I asked clients during one-on-one coaching for creative business owners.  I honestly didn’t know how effective it would be, since I wrote it myself, but my past self really came through, asking questions my present self really needed to answer.

While working on it, I decided I would share most of my responses here on the blog.  I regularly receive questions about the ins and outs of my business, so I thought this might answer some questions or offer insight into what I’m working through and considering.  The guide is long and thorough, so I’m just sharing parts of it, but it will still give those who review it an understanding of where I’ve been, where I am, and where I’m going.  If you would like to walk through the guide for your own business, you can download it for free HERE.

How did I get here?

What lessons have you learned since you started your business? 

So many.  Too many to name, but I think the most valuable thing I have learned is how to keep going.  Through moves, through transitions, through change, through endings, through successes and failures, through doubts and fears.  I have learned to put one foot in front of the other and to pivot on my heel when needed.

How have you grown as an entrepreneur? 

While imposter syndrome still rears its head, I have embraced being the captain of my ship.  I feel more confident in my instincts and my navigation ability.

How have you surprised yourself? 

I never thought I would claim the title of artist, and I finally have.  It’s even on my business card now.  I’m also surprised I’m still doing this.  I never gave much thought to a five or ten-year plan.  I felt like I was along for the ride and would go as far as it took me.

What is your greatest professional accomplishment to date? 

I think starting my blog was the greatest professional accomplishment.  It was the starting point and the avenue that led to all the other opportunities, from becoming a vendor at Lucketts to launching the milk paint line, publishing books, and becoming a working artist.

What would you change if you could?  (If anything.) 

I wish I hadn’t let negative comments or feedback sway me as much as they did in the early years of my business.  I made a lot of big decisions based on a small sample of discouraging feedback, sometimes from just one person who didn’t even know me.

Assessing the Now

What do you love about your business? 

I love that I get to do creative work for a living.  I recognize that it is a gift, and even on my bad days, I really do love it.

Why did you start this business, and who did you start it for? 

I started it to contribute to our monthly income, for my family.  I think, though, if I’m sincere, I started it for myself.  I felt utterly lost and isolated as the stay-at-home mom of two boys under the age of two.  As much as we needed the money, I also needed work that could be completed, and I needed to connect with a community of creatives.

What are the sources of anxiety in your business? 

I am anxious about security, stability, and my place in the changing online landscape.

What aspect of your business feels most important to you (impactful, rewarding, valuable)? 

My fine art painting and writing feel the most important to me right now.  I enjoy both; they are equally rewarding, and I feel like they are a legacy I can leave behind.

What fills you up and what drains you? 

I am definitely filled up when I’m engaged in creative work.  I love it when I have a spark of an idea to write about, I have to sit down that second to capture it.  I love it when I see something that compels me to paint.  I also enjoyed the hunt – reading, traveling, going to museums, and antique shops in search of the next thing that speaks to me.

I am drained by the administrative aspect of running a business – insurance, taxes, paperwork, and balancing my ledgers.  Playing the social media games is also draining for me.  It’s always a struggle to stay authentic to myself while also striving to please SEO, algorithms, and social media giants.

What is the current financial state of your business? 

I’m obviously looking at it in more detail than I will share online, I’ll simply say that business is financially healthy and operating in the black.

What is the most profitable area of your business?  Are you devoting enough time to nurture that area? 

The most profitable area of my business over the past couple of years has been advertising and sponsorship income from my blog, but I anticipate this changing in the next couple of years as the online landscape and my interests evolve.  I am currently evaluating how to continue nurturing my blog while also expanding other revenue streams.

Do you have any employees/contractors other than yourself?  If so, do they have clear job descriptions?  Are they doing their work to your satisfaction? 

I have one part-time employee who has been with me for over ten years.  Since we’ve worked together for so long, we’ve operated independently most of the time, but this is a good reminder for me to review and update her job description and check in with her on how I can improve as an employer.  (I just updated her job description and emailed her to address this.)

I feel like I’m doing too much…

Second-guessing myself and my ideas.

And not doing enough…

Just giving an idea a try and see how it goes.

How can you change that? 

I need to stop dragging my feet on ideas I want to try and test them out in small, low-risk ways to get started.  If it works, great!  If it doesn’t, that gives me more space to try other ideas.  While I’m not scared of failure, I can be scared of trying something that turns out to be stupid.

Identifying Core Values

What is meaningful to you? 

Doing work with my hands, making things I’m proud of, and encouraging others to find their creative spark.

How do you want to be known?  What are the things you want other people to think and say about you? 

I want to be known as an encourager.  I want people to say they read something I wrote, saw something I made, or heard something I said, and it helped them to live a more creative, fulfilling life.

What qualities are most important to you in your friends and the people you collaborate with professionally? 

Authenticity, generosity, and honesty.

What are your non-negotiables?  What will you never, ever do? 

I’ll never compromise my standards even if the potential reward is substantial.  As much as it is within my control, I won’t go into debt.

Finish this sentence – I will walk away from my business when (or if)…

…I hate what I’m doing.  I can’t imagine that day, though!

Write down the recurring words and themes…

Inspiration.  Encouragement.  Creativity.  Art.  Authenticity.  Generosity.

(I skipped the section on Solving Problems, and I’m going to post about that separately so that I can dive in a bit more detail.)

Daring Dreams

What were your dreams for your business when you first started? 

I wanted to make at least $200/month to help with the family budget.  I also dreamed my home and/or work would be featured in a magazine.

Which of those dreams have been realized? 

Both of them.  Beyond my wildest expectations.

What do you dream your business will look like in one year?

• My new book (released this summer) will be a best seller and exceed all expectations.
• I will have established a more comfortable balance for my primary creative endeavors – art, writing, and home.  I often feel stretched thin, and I need to find a more sustainable way to make everything fit into a healthy workweek.
• My artwork (oil paintings) will become a more prominent, steady part of my business.  I’d love to see more pieces in designers’ collections in stores.

What are your biggest, most daring dreams for your business?  (Daring dreams don’t have to be big by the world’s standards like, “I will be a millionaire in one year”.  They can be small things that would be a big accomplishment and a game-changer for your life like, “I want to be able to pay myself $500/month to help with bills and groceries.”) 

• A best-selling book
• Recognition for my art (through either features and/or awards, acceptance into a gallery or show, etc.)
• My pattern and product designs are sold in stores, beyond print-on-demand.
• That I can write, paint, and share until I’m ready to retire.

What could prevent you from realizing them?  Are there any potential roadblocks or constraints?

Focusing on the wrong things, like chasing vanity metrics instead of creating.  If I’m not writing, painting, and making things, none of those dreams can happen.

What could help you realize them?  Big dreams are often reached in baby steps.  What will get you headed and walking in the right direction?

I think it really is about how I spend my days.  I won’t paint something I love, write something that resonates, or design something that sells if I am not painting, writing, and creating daily, or at least regularly.  I’m going to have a lot of mediocre paintings, slop writing, and ho-hum design ideas, but I’ll never achieve big dreams if I’m not putting in the hours.

How are you going to invest monetarily in the future of your business?  Think about what you need to save for new tools (camera, computer, office equipment, art supplies, etc.) in order to continue to grow.  Also, think about planning for unexpected expenses or having some “seed money” for ideas that haven’t even presented themselves yet. 

I will eventually need a new computer, and I have savings for that when the day arrives.  Beyond that, I do need to invest in a new camera specifically for filming videos and streaming.  My DSLR cameras are too old and antiquated for the projects I want to launch this year.  I’m currently researching streaming and multi-camera set-ups and will buy what I need soon.

How are you going to invest in yourself as an entrepreneur?  (Mentoring groups, courses, conferences, books, etc.) 

I am still meeting monthly with a fellow artist and creative entrepreneur I met in a Mastermind Group, and that has been valuable and enriching.  I will continue to meet with her.  Since I took an international trip in 2025, I don’t have any big trips planned for 2026.  I want to look for more local museums to visit, and hope to plan a local creative retreat later in the year if my schedule and budget allow.

How are you going to invest your time in future projects?  It’s easy to put all your time into what’s happening right now, because it is imminent, but it’s important to take time to nurture those ideas and projects that might launch in a few weeks, months, or even years. 

I am already working ahead on two more books, so those are the big future projects I’m chipping away at regularly.  I am also working on some design projects, future original art sales, fine art print options, and offering more paint-along tutorials/lessons.

So, now that I’ve done a lot of thinking through my business, here in this post and on paper, I need to get down to the nitty-gritty details about what all of this practically looks like.  What does my schedule look like?  What are the action items?  What daily habits do I need to put in place or keep in place?

I’ll be sharing more as I work through some of these questions…