The Ultimate Slow Season To-Do List for Entrepreneurs: How to Make the Most Out of the Winter Season for a Thriving Year

The Ultimate Slow Season To-Do List for Entrepreneurs: How to Make the Most Out of the Winter Season for a Thriving Year

I’ll always advocate for rest and relaxation over the winter months, but if you’re the type who likes to go, go, go, you may find yourself squirming at the thought of staying still as the rest of us ease into the slow season. On the other hand, you may have such a packed season ahead that there’s no better opportunity than winter to tackle your to-do list. You’ve been adding to it all summer long, after all. Wherever you find yourself, I see you. As a wedding photographer and a licensed attorney, serving creative entrepreneurs with legal resources + counsel is the perfect marriage of both my careers. If you’re wondering how you can make the most of your time before your calendar gets busy again, you’re not alone.

Here’s what I’m doing to get ahead in my business while my days are a little quieter this winter...

–I’m taking it back to basics. 

When’s the last time you reflected on your elevator pitch? Despite everything that fills your days as an entrepreneur, what do you truly set out to do in your business? What’s your mission? How do you want to make people feel? What’s your why? What are the promises you make? How does your impact make a difference?

From there, take some time to think about your ideal client. Describe the dreamiest inquiry you could receive–emphasis on the person doing the inquiring, of course. If every client of yours were to look like them, you’d be happy as a clam. At a basic level, what is this person all about?

What do they do for work? How much do they earn? What do they do to unwind at the end of the day? Where do they live? In a high rise in the city? A cottage in the country? What stage of life are they in?

Now, take it one step deeper:

How do they live their lives? What do they hold dear? What are they afraid of? What brings them true, lasting joy? What does a perfect Sunday afternoon look like for them?

Finally, how do you fit into their story? How is your expertise going to help them live the life they always imagined? How will you empower them to find success at every turn?

I'm sure you've thought about these things before, but if you haven't written them down, now's the time. It’s important that you do. These are the questions that turn a side hustle into a beloved brand built to last (and you’ll return to them more often than you think).

If it’s been a minute since you’ve considered these foundational elements of your business, it’s time to come home to them. Chances are, things have changed–and you owe yourself an update. With some reflection, you may realize the philosophies that supported your business have changed a little (or a lot). You might see a new path become clear. You could discover that the people who were once your dream clients aren’t anymore.

This is the time to ponder the big questions for your business (and yourself). Not only is this essential for the clarity of your purpose, but it’s the first step to making meaningful, fulfilling work.

–I’m reaching out for fresh testimonials and conducting market research.

Testimonials are one of my favorite ways of knowing whether I’m on the right track. I’m unafraid to ask my clients for the things that may be hard to hear. What worked? What didn’t? Not only is this your opportunity to improve, but it’s also your chance to ask questions that will get you stellar social proof. 

Here are some of the questions I ask my clients to get stellar social proof I can list on my website with pride: What would you tell someone who’s on the fence about working with me? Did you walk into this experience with any skepticism? What was your legal strategy like before we worked together? What about it wasn’t working? When did you realize you needed help? 

These questions will help you get juicy testimonials, but they’ll also double as market research. The more you survey your clients, the more data you’ll have to observe trends in their response. This will help you craft relevant messaging around your offerings and promise the results to match.

–I’m auditing and optimizing my offerings.

By collecting market research, you'll have the insight you need to better match your services with what your clients are looking for. This is your chance to be ruthless–cut what doesn’t work and replace it with something that does.

Here are clues to tell if your offer suite needs updating:
–Is there an offer you never book? In contrast, is there an offer you can’t stop booking?
–Which service of yours gets the most questions? This could indicate a disconnect in your messaging.
–What do your clients often request as an a la carte addition to their package? On the other hand, is there a line item within one of your packages that no one seems to care about?

Remember, you’re on a mission to solve problems and answer questions, not create them. When in doubt, simple is always best. Just because it’s published on your services pages doesn’t mean your offer suite is set in stone. If you’ve been waiting to develop an idea or bring a new offer to life, let this winter be your chance to make it happen. 

–I’m making time to sharpen my skills, learn new things, and master my craft. 

Can I get a round of applause for all the online courses I’ve bought and sat on for six months? Now’s the time to dig them up, dive in, and binge (or whatever your learning style allows).

As entrepreneurs, we should seek every opportunity to improve. Online courses are one of my favorite ways to make that happen. With an abundance of instructors and industries in the online education space, there’s something out there for everyone. Whether you need to brush up on your technical knowledge, improve your client service, optimize your systems, or discover a new way to lead your business with heart, there’s an online course for you. You could also seek the support of a business coach or a mentor to help you identify the blind spots in your business.

Whatever you choose, there’s so much out there to learn. Your continued expertise is part of why your clients invest in you. Take it slow, celebrate the baby steps, and implement as you go.

–I’m circling back on my contracts and double checking my legal strategy.

Around here, this one goes without saying, but I’ll say it anyway–your contract should protect your business at every opportunity. And being knee deep in litigation is too late to learn that it doesn’t. 

Use the time you have this winter to have an attorney run their eyes over your contract. Lean on their expertise to identify the holes and the risks they could pose to you. Turns out, your legal sitch may need some life support. In that case, you’ll save money by starting from scratch and replacing your contract altogether instead of paying a lawyer to revise what you already have.

My online shop has attorney approved, done-for-you contract templates with lifetime updates for every kind of entrepreneur, so you’ll never have to worry about yesterday’s contract for today’s legal implications. I’ve got you covered (for life)!

Click the link below to shop.

Shop The Artists’ Lawyer Contract Collection

–I’m pouring my energy into copywriting that converts. 

Remember those shiny new testimonials and that market research you did? This is a great starting place to gain new insight into your client experience. Before you worked together, what was their life like? What did they struggle with? How do they feel now that you’ve stepped in and solved all their problems? 

Identify trends in the words they use, how they talk about their lives, and the feelings they describe. The best kind of copy in the world is the kind that has your clients saying, “How did Magi get in my head?!” We don’t have to imagine what our clients are thinking–turns out, we can just ask. You don’t have to hire a copywriter to give your messaging a little facelift this winter!

–I’m scheduling a brand shoot to get new headshots and update my visual identity.

Have you ever gone on a Tinder date with someone who looked nothing like their profile pic? Don’t give your business that kind of treatment. In addition to my law practice, I also lead a boutique wedding photography studio, so I can’t emphasize this enough: The imagery of your brand is the first step to establishing “know, like, trust” with new clients.

Through the mood and curation of your visual identity, prospective clients can inquire with confidence knowing your website (and your Instagram) shed some light on what you’re all about. Photography is where it begins. Even in the low light of winter, I prioritize capturing branding photos that align with my aesthetic, serve my marketing strategy, and keep my content fresh + relevant. 

–Most of all, I’m making time for rest.

The best way to make your busy season as successful as can be? Rest. Sleep in. Take naps. Go to yoga. Drink water. Fall asleep when you’re tired. 

If there’s anything on this list that you prioritize this winter, let it be this. We both know that you can’t pour from an empty cup. And even though you’re reading this after a laundry list of offseason to-dos, listen here: You deserve to rest, heal, and restore without shame. In fact, I’d like to have a stern word with anyone who told you that unless you’re exhausted, you’re not doing enough. If you’ve been looking for a sign to take it easy, this is it.

What’s been on your backlog that you’re looking to tackle this winter? Big or small, send me a note and share so I can celebrate with you. 


Hi there! Welcome to my free resources page, where I share all kinds of freebies, templates and guides for creative business owners, artists, and entrepreneurs.

If we haven't met yet, hi! I'm Magi. I'm lawyer, educator, photographer, storyteller, traveler, and entrepreneur. My journey has taken her from photographing professional surfers while swimming in some of the world's most epic waves to receiving a Juris Doctorate from Rutgers Law.

If I'm not photographing a wedding with my husband, Scott, in a remote locale, managing our team of Associate Photographers, or providing legal counsel to creative business owners, then you can probably find me eating an açai bowl, chasing my pup, Arti, around the beach, or watching SVU reruns in our bungalow.

I hope you find these intentionally-crafted resources useful, and if there's anything else I can do for you and your business, please reach out!

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This information is made available for educational and general informational purposes only; it is not legal advice for an individual case nor does it guarantee any future result. This material may be improved upon or updated without notice, and The Artists’ Lawyer will not be held responsible for any outcomes as a result of this education. Do not act upon this information without seeking individual advice from a lawyer licensed in your state. You understand that viewing this information does not establish an attorney-client relationship between you and The Artists’ Lawyer, or the founding attorney, Magi Fisher.

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