10 Things All Freelancers Should Be Doing

The life of a freelancer can be unpredictable — and let’s be honest: that’s why we love it! — but  sometimes that can lead to overwhelm, disorganization, and chaos. To combat those feelings, we suggest implementing systems into your life and work that incentivize consistency, reduce stress, and eliminate the obstacles that stand in the way of getting things done. We’ve compiled a list of ten practices that will position you for greater success in your life as a creative professional. Stay savvy!

1. Keep your digital presence up to snuff: Most of your fans, potential clients, and community will first engage with you online, so it’s important that you treat your online presence as a living thing. Websites and social media profiles require long-term care and maintenance — and the same goes for any place that you exist on the internet! Stay up to date, Ponyboy.

2. Stay on top of your budget: Even if it’s as simple as a spreadsheet in Numbers or Excel, tracking your income and expenses in real time will give you a clear and consistent picture of how much work you have or need — and it’ll make tax time a breeze! Bottom line: you’ve got to keep an eye on your bottom line.

3. Learn how to overcome rejection: We know it’s kind of a bummer to talk about, but the more you can get comfortable with rejection as an undeniable presence in your life as an artist, the quicker you’ll be able to move through those feelings. Remember: for any opportunity you don’t get, there are 100 reasons as to why. The odds would say it isn’t personal. 

4. Always have a contract: It’s always best when everyone’s looking at the same map. Cover your bases and hold all parties accountable by outlining the nature of your work, performance, or relationship in written form. Include the scope of work, costs, and timeline. Google is chock full of sample contracts and agreements if you need a template to get you started!

5. Know your competition: Your goal is to be so singular in who you are, what you do, and what you offer that you stand apart from all of your competition. In the arts, of course, there is a lot of competition. If you can articulate what makes you the expert in your niche and communicate that wherever your brand  lives, folks will take notice.

6. Use the right tools: Do the things you use everyday actually serve you? Think of the supplies, equipment, and software you use to conduct the business of your art as items in your toolbox. Everyone’s needs are different, but if you hone your collection over time (trial and error), you’ll have a mastery of each tool and greater efficiency in your overall operation.

7. Save and back up your work: In the cloud. On an external hard drive. Whatever your preference, do it often. Don’t learn this lesson the hard way!

8. Stay in the know: Just like your digital presence, your base industry knowledge should be approached (and cared for) like a living, evolving thing. Read books and trade publications, download podcasts that speak to your field, and attend workshops and classes. Staying viable and relevant relies on an ongoing understanding of the landscape in which you operate.

9. Balance work and life: Easier said than done, but boundaries help! Boundaries may take the form of a regular schedule, but if that doesn’t work for you and your business, at least try unplugging for a few hours each day. We think you’ll be surprised about what that can do for your mental acuity.

10. Keep the hustle alive: Some days bring three new opportunities and several hours of deep productivity. On other days, responding to a few emails is an accomplishment. Take pride in your forward momentum and forgive yourself for any setbacks. Do what you can to stay engaged, inspired, and hungry. Don’t get comfortable. Get after it.

Still feeling overwhelmed? Need a hand? Schedule a call.

Getting to Know Our CEO

A company and its culture are a product of its people, and today we’re talking with our Founder and CEO Lori Rosolowsky about founding the company, finding inspiration, and the future of Open Sky Artists.

What was the path you took to get to where you are today?

It’s been a winding one. I started studying piano at age 5, but I majored in environmental science in college (minored in classical piano performance). I came of age during the 1970s when pollution, extinction, and overpopulation worries were dominant.  I then earned a PhD in pharmacology (the flip side of toxicology). In the mid 1990s, after working as an environmental consultant in a very family-unfriendly company, I had to shift my work-life balance. By then, we had a toddler, and my husband also had a demanding job. It was scary to leave my career and abandon my income but, it allowed me to reinvent myself as a piano teacher, performer, and primary caregiver to our son. Soon after, I combined my environmental calling with my musical passion and often planned, produced and performed in concerts for environmental causes and progressive candidates. Over the years, I grew my musical skills, becoming a singer-songwriter, jazz pianist and theatre music director. A song I wrote about a fraudulent election landed me in the finals of a national songwriting competition and was used as a theme song for a radio show about election and voter protection. I co-hosted that show for 3 years (2006-2009). When we moved to Montana, I left behind an active performing career in which I led a jazz quartet, a vocal trio, music directed and acted in community theatre, and performed solo and with several other organizations.  

Why did you start this business?

For practical and philosophical reasons. After 25 years in Pennsylvania, we moved to Montana in 2016, where I was a “nobody.” I continued to seek gigs in my old state where I had spent years cultivating relationships, but I also needed to refer jobs to colleagues since I didn’t live there anymore.  Open Sky Artists started out by mostly getting bookings for other people, with some ancillary promotional services.  

The philosophical reasons are what make me passionate about the business and have driven me to make Open Sky Artists different from other companies that assist people in the performing arts.  First, we recognize that artists need a champion at every step of the process, not just to get a gig. Second, our non-commission based model allows us to create and implement opportunities for artists beyond one-off performances. Third, I’ve had painful experiences with promoters who shut me and my partners out of the conversation and did not act with integrity. They acted as gatekeepers instead of door openers. That behavior is a deal breaker for me. Anyone with whom we work can trust that we are working in their best interest at all times, with integrity, trust, transparency, excellence, and inclusion. I am immensely proud of our track record with those values and love to share with people how we’ve responded when we’ve been put to the test.

What has been the most challenging part of running Open Sky Artists?

Learning to think like an entrepreneur and investing in coaching that allows me to serve my team and my clients as well as I can. Balancing the value of the work our team and I do with clients’ budgetary constraints and being creative in developing billing models so we can serve our clients. Running Open Sky Artists has taught me so much about myself. It’s given me many opportunities to walk the walk when it comes to my values.  

What has been the most rewarding part of running Open Sky Artists?

I recently opened a fortune cookie that said, “Don’t wait for things to happen. Happen to things.” That’s what we do! We “happen” to the people, ideas and things so they can do what they love!  I’m happy about the bond I have with my team and our clients. Open Sky Artists is a professional extension of how I live my life. I like “happening” to people! 

What do you do when you’re not busy with Open Sky Artists?

I’m addicted to nature and fitness, especially swimming (competitive) and yoga (non-competitive, duh!), with a healthy dose of skiing and biking when possible. I’m super involved in Bozeman, Montana as a volunteer in educational and cultural organizations. I’m blessed with a wonderful husband and two sons, one of whom is still at home. Being a loving wife, mom, and friend who drops everything when someone is in need—that’s my life’s purpose.

Who inspires you?

Climate change activists. Single parents. Caregivers of the elderly. Survivors, refugees, and their champions.

What art inspires you?

I’m as moved by creations from local, unknown artists as those on big stages.  I have some young piano students who compose music with dissonance and rhythm that you’d never find in a beginner piano book; many of the community theatre productions in Bozeman are as impactful as shows I’ve seen on Broadway; art created from materials that would otherwise clog landfills inspires me; so do productions that involve underserved communities.

What do you feel is the biggest strength of Open Sky Artists right now?

I’m going to pick two! First, our team. It’s really hard to find people with the skill sets and mindsets needed to do this work. Our team members are bright, multi-talented, experienced, devoted to outstanding service, and fun. Because their skills complement mine, our clients get robust services delivered with integrity. Second, our clients. I’m thrilled that people with big ideas and bigger hearts are finding us and want us to help them.  

What do you see for the future of Open Sky Artists?

I look forward to continuing to serve our loyal clients who’ve been with us since we started, and all the new people we are connecting with—they have something to say with their art, and it’s a joy to help get their unique voices heard and appreciated.  To me, our future feels boundless, like an open sky.

Any parting thoughts?

One of my mantras is “when things are tolerable, you tolerate them; when they are miserable, you change.” I left a corporate career for which I had trained my whole life because the working environment was miserable and not compatible with family life. That allowed me to pursue music professionally and eventually start Open Sky Artists, which has been such a blessing. Like the fortune cookie says, “Don’t wait for things to happen. Happen to things.”

Learn more about Lori and the rest of our team.

A Good Old-Fashioned Q&A

You asked. (Frequently!) We answered:

What exactly does Open Sky Artists do?

We offer innovative strategic guidance and an expansive range of in-house branding, booking, marketing, design, and creative services to creative professionals in the performing arts. We build your brand and audiences while you do what you love.

What makes Open Sky Artists unique?

Unlike agencies that only secure bookings offer advice, we are a one-stop shop for getting things done. Our clients have the flexibility to work with us on a yearly basis or project-to-project, and because every client is different, our plans are highly customized. Our love for out-of-the-box thinking and relationship building means we know how to find opportunities in hidden places.

We are working artists with business expertise, so we understand the value of investing in our art; we get what you need because we do what you do. And if booking more gigs is what you’re after, good news: we don't charge commissions, and we’re not exclusive. 

What are your company values? 

Integrity, excellence, diversity, creativity, individuality, and adaptability. We are transparent and trustworthy. We celebrate the things that make us different. We are seriously committed to our clients’ satisfaction. Read more about our core beliefs here.

What kinds of clients do you serve?

We serve artists and the institutions that rely on them — wherever they are. Our current client base is comprised of freelancers, creative professionals, and arts organizations throughout the United States. 

What does being a client actually mean?

Guidance, direction, and focus! Clients have access to our wide range of in-house design, branding, booking, marketing, and creative services. You’ll connect with our ever-growing network and benefit from highly customized strategic guidance and industry know-how. If you’re an institutional client, we’ll function as an extension of your team. Your goals are our goals — even when they change.

What services do you provide?

Logos, marketing campaigns, websites, press releases, and promotional print — to name a few. If you’re interested, you can read a pretty comprehensive list of our services here.

Do you design websites?

Heck yes we do! We also redesign existing websites that just need some love. See what else we do here.

Can I do some of the services you offer myself?

Of course! We want you to do what you love — and outsource the rest to us.

What if I need help with something that’s not on your list of services?

Talk to us! We are constantly learning new skills and meeting new people. If we aren’t able to help you out, we will find you someone who can.

What will it cost me?

Our projects can cost a couple hundred bucks or a couple thousand — it truly just depends on what you need! Clients who commit to a year-round Everest Plan save on our services. Schedule a call and let’s talk about what you want to achieve!

Do you guarantee artists a certain number of bookings?

We have an ever-growing network of arts organizations and presenters across the United States. While we can’t guarantee that you’ll land a gig, we promise that you’ll have a strong digital presence that positions you for success — and we’ll work together to evolve the strategy for better success.

How do you measure results?

We measure results based on your particular, evovling goals. We look at every aspect of your project to make sure you receive the best quality guidance and services for your investment.

Other questions? Schedule a call.