How to Invest in Yourself at Any Price Point

When I moved to warm and sunny Bermuda from cold and dreary Boston back in 2016, I knew I wanted to do 2 things: 1) to bring more of my entrepreneurial side to my music career, and 2) to grow food year-round. 

I had ZERO idea what either of those things looked like.

As far as my music career had always gone, I just waited for opportunities to come from others–contractors, presenters, administrators, conductors, etc. I wanted to have more control over what, where, and with whom I performed. As for my garden? The idea of growing through the winter, and into what was basically a bed of limestone rock was totally intimidating. 

Both were going to involve a lot of learning, and likely quite a bit of investing in time, energy, and money. 

Unfortunately, I had also just given up a significant portion of my income, and I didn’t have a ton (or any, really) money to spend on said learning. 


Listening to Podcasts on my daily walks


Back then, I turned to freebies like podcasts and blogs for my business, and youtube and the free (and, it turns out, pretty toxic) “compost” available at the dump. (Remind me to tell you about the time a truck dumped a car-sized mountain of crappy “compost” at my (very steep) driveway just as a hurricane was arriving.)

Ah…good times. 

I didn’t have extra cash to put towards these projects, but I did suddenly find myself with loads of time. So that’s what I invested with for those first few years. The time it takes to piece together bits of free info from podcasts, and the time it takes to turn kitchen scraps into the perfect soil. 

Now, 7 years later, I regularly dedicate a portion of my income each year on coaches, courses, retreats, and masterminds in order to get expert eyes on my business, build relationships with my peers, and learn from the best. We’re also now able to spend more on materials to build raised beds, organic compost, and fertilizers, and water lines for the garden. 

But there are plenty of options between that free podcast and a $15,000 Mastermind, and there are pros and cons to all of them. I want to outline some of the options at every stage of the game (and we’ll drop the gardening metaphors….for now… and stick to building careers in the arts  ;- ) 


Photo by Andre Taissin for


Whether you are a performer looking to book more concerts for yourself or your ensemble, a writer looking to grow their audience or someone with a creative dream project you are eager to get off the ground, there are GREAT ways for you to start investing in yourself at any price tag. 

Okay, here we go! 


Level 1: It’s Gotta be Free! ($0)

1. Podcasts
2. Blogs
3. Youtube
4. Joining someone’s Mailing List (often via a freebie that you get by entering your email address) Bonus–gets you some great (also free) material in their weekly emails/newsletters as well. 

I’m listing all of these in one place because they all give you similar experiences with similar Pros and Cons. One of the most important lessons I learned–a concept I think about every single week in my career, is something that I learned from a podcast. And even though I’m now at a point where I can invest in great coaches, I STILL take in free content on a daily basis. (Read to the end for a listing of a few faves.) And…shameless plug, you should hop onto my mailing list. I send out a weekly email each Friday with a few bits of info/tips/hacks that I think you’ll find useful.


  • Obviously, the fact that it doesn’t cost you anything is the biggest one. 
  •  Because there isn’t an initial buy-in, you’re free to try multiple people’s content on for size. 
  • You can take in the material however and whenever you want. 


  • While we all give out great content for free, no one is giving out ALL of our content for free. So you need to understand that while what you’re getting will get you started, it will only take you so far. 
  • It can get confusing and overwhelming if you’re taking in content from several different people at once.
  • You don’t have access to any of those people. You can’t ask them questions about your own situation. You need to take what you hear and see if it applies to you. 


Photo by Melanie Fiander


Level 2: I’m ready to dip a toe in and see how this goes (between $25.00-$500.00)


1. Webinars and Online Bootcamps

Most webinars and bootcamps (short, 1-5 day online challenges) used to be free, and some still are! But with the end of the Pandemic came busy schedules, and fewer people stuck at home, waiting excitedly for ANY adult human interaction and hosts started finding that people would sign up for a free event and then blow it off. However, when people pay, they pay attention, so even charging a minimal amount like $25, was getting them into the metaphorical room. 

With Online Workshops, Webinars, and Bootcamps, the teacher is usually offering it right before the launch of a bigger program. We all do it to gather people who might be a good fit for our program, get them started, and then let them know about the bigger offer. Is it a sales tactic? Yes. But I don’t know anyone out there who isn’t busting their butt trying to give amazing content and information in these free or low-ticket events.

The last thing we want is for anyone to feel like they wasted their time with us.  This is NOT, I repeat, this is NOT one of those time-share scams where they get you in a room and the ONLY thing you learn is why you should give them all of your money.  The idea, rather, is to teach you something truly useful, and give you a chance to see what it’s like to work with them. 


  • They are short-just an hour, to a couple of days.
  • You get to see the teacher in action in real-time, and can often ask questions and interact with them live.
  • You’ll come away with at least a few clear action steps or ideas
  • A great way to find out if you want to invest longer-term (or higher ticket) with a coach or teacher.


  • You’re getting just a taste
  • Not getting in-depth coaching or long-term help
  • Only offered for a limited time, and usually have limited access to any replays.


2. Digital Mini-Courses: 

You can find various mini-courses on all sorts of topics. From how to master Instagram to SEO, to Excel Spreadsheets. These are pre-recorded and when you pay for them, you’ll get login information to access the course. 


  • You can pick and choose exactly what you need to learn. 
  • You can learn it at your own pace and as your schedule allows. Binge all 8 modules in one sitting, or parse it out 10 minutes at a time. 
  • You’ll have access to them forever. I have many digital courses in my Kajabi Library  (a popular platform that “houses” digital courses) that I refer back to often. 


  • Again, there’s usually no personalized support from the teacher themselves.  (some people will launch these mini-courses at a certain time of year, and offer a FB group for a certain amount of time–but this is usually peer support) 
  • They don’t go very broad,  But again, if you just wanted info on 1 particular topic, these are perfect. 


Level 3: I’m ready to make a real investment ($2000-$100,000+)


1. Group Coaching Programs

These group offers generally run between $2,000 and $8,000 with some running significantly higher depending on the length of time, number of trainings, and other factors. 

Generally, these sessions are held live and online. 

One of my best friends is someone I met in my first live coaching group, 3 years ago. We Voxer each other multiple times a day, every single day. 

Two people who were in one of my first rounds of Profit Pivot just met for the first time IRL–2.5 years later! They were at the same conference and sent me a selfie that warmed my heart. 


  • You have an amazing group of peers that you get to meet and interact with and bounce ideas off of. This kind of work gets lonely really fast–and having others there alongside you can go a LONG WAY. 
  • You have real-time access to the coach. You can ask questions, usually have a FB group, or a way of communicating with your coach via Voxer, or email, and you’re getting their eyes on your work on a semi-regular basis. 
  • Small and intimate groups. Usually, these groups are between 3 and 20 people. Any larger than that, and I think people can start to feel lost in the shuffle.
  • The Coach is fully invested in you, gets to know you and your projects, and will help you see success.


  • You’re sharing the coach’s time with the others in the group. 
  • You’re following a syllabus that may or may not align perfectly with what you are doing/needing at the same time. 
  • You need to be available for the coaching times, or watch the recording later on….alone…and sad that you missed out on the fun. 


2. 1:1 Coaching

Again, this varies greatly in price depending on the kind of coaching, the experience of the coach, and how much access you get from them. They can run from $500 a month to (I kid you not!) $50,000 a session. To give you an idea, I see my 1:1 clients alone every other week for 90 minutes, hold office hours every week (basically just a giant work party/Q&A session that all of my group and 1:1 clients are invited to) and they can Voxer me whenever. My fees are now around $1,000 a month. 


  • Your coach is focused on your work, and helping you succeed. 
  • With 1:1 coaching, you have the time to thoroughly work through mindset and thought issues that there just isn’t time for in group coaching settings. 
  • Strategizing is specific to your needs and on your specific timeline. Whatever you need help with at that moment is what you’re getting. 
  • 1:1 coaching can lead to incredible growth, and you’ll see the fastest level of personal growth.


  • Usually there’s no peer support (that’s why I hold my office hours, so all of my clients can meet each other)
  • It is a big investment. 
  • I’ll be perfectly honest with you. With 1:1 coaching, things get real. It can feel uncomfortable as you face your own limiting beliefs and are held accountable for the things you say you want to do. As a coach, it’s important to both encourage a client’s growth, and to always meet them where they are at that moment, and as someone who is regularly on both sides of that table, it’s important, and sometimes uncomfortable work. 

3. Masterminds

There are 2 basic kinds of Masterminds, but both lean heavily on the peer dynamic. A paid mastermind is put together by a coach, and the members are hand-picked or can apply, but the group is held to a certain standard (income level or type of work are typical) Instead of following a training syllabus like in a group program, masterminds give each member time in the “hot-seat” to talk about their projects, and ask questions, talk about where they are getting stuck, and get ideas and insights from the rest of the group. 

Unpaid masterminds are put together by a group of peers themselves. I was in one with a couple of friends back in 2019! And it was a huge kickstart to the early days of my business. Brendon Burchard put one together with his besties (Amy Porterfield, Jenna Kutcher, Lewis Howes, etc.) and although they don’t pay to be IN the mastermind, they all commit to getting themselves to wherever they are meeting in person–covering their flights, hotel rooms, meals, etc. (*Also, what I would give to be a fly on THAT wall!) 

Some of the better-known mastermind groups can run up to $25,000 or $50,000. But then, you’re paying for access to the greatest business minds out there. 


  • You get the true inside-scoop. What worked, and what didn’t? How they did what they did. The nuts and bolts. 
  • You can ask for help, resources, and connections. One person made a “shot in the dark” request for an email introduction to a very famous person in the Theater world,  and it just happened that Super Famous Guy had been a teacher, mentor, and college advisor to another member of the group. Connection MADE.
  • At the highest levels, these masterminds are like mini-marketing departments. They speak at each other’s events, promote each other, and help to create a serious buzz.


  • You’re expected to keep up. Mastermind is meeting up in Cabo for a long weekend and everyone is staying at the same 5-star resort? You’re going to Cabo, and you’re shelling out the big bucks.
  • This is not just about you. You’re there to help everyone in that room. (while they are also helping you, of course)
  • It’s a big investment. You want to be absolutely sure you have the time, money, and bandwidth to take on a group like this, and you want to be absolutely sure this is the right group for you. It will change your life, but you have to be willing to show up.



Looking back, I can’t believe how far I’ve come. From pulling the old dead plants out of the dried-out pots or the garden beds with 5-year-old soil I had them in, and planting new ones in their place. No surprise, they weren’t terribly successful.

Eventually, I learned that I needed to build up that soil with nutrients. Good nutrients–not cheap chemicals. And that those good nutrients could be free with compost that I made slowly and patiently, one banana peel at a time, or with slightly more expensive bags of compost or chicken manure that I bought at the garden center. Those things allowed my flowers and vegetables to thrive and succeed, and our careers are no different. 

Investing in ourselves is a necessary step in our growth, and I have yet to see anyone succeed without doing it in some form. If you have all kinds of time but are short on cash, go for the free things. It will take you much longer, but you WILL be getting good information. If you have less time, and or, a bit of money to put towards it? I can promise you it’s worth it. It will fast-track your growth and get you there a lot sooner. 

It took me from 2016 to 2020 to get to the first step with free content, and then a year of a group coaching program to get to the next step, and less than that with my current mastermind group. 



Would I have done anything differently? No. Honestly, at first, I wasn’t perfectly clear on what it was I wanted to do, and I didn’t have cash on hand to pay for programs or courses. The free content got me started. I felt inspired and encouraged to keep going. 

But I will say that I am SO glad that I DID, eventually choose to invest in that first coaching program and each course I take gives me so much new knowledge. I think it does need to be done at some point. It’s worth saving a little bit each month at the beginning in order to start seeing real growth and progress at some point. 

I’ve experienced it first-hand, and I’ve witnessed it with my clients. 

Have you taken a course or participated in a group program, or do you have a favorite podcast? Let us know in the comments so we can all share resources. You can find my round-up of favorite podcasts for creative entrepreneurs HERE. It’s a bit outdated and leans toward musicians, but while a couple of these podcasts have changed hosts, they are still around, and are all still amazing! I’ll do an updated post with some of my new finds soon (and I’d love to include some of yours, too!) 




P.S. If you enjoyed this blog post and want more insider info on how to thrive as a creative, be sure you get on the list to receive my Friday “Weekend List.” Each one is loaded up with additional tips, tricks, and things to think about, including a new curated list of articles, books, podcasts, and things that I think you’d enjoy.  Click Here to Get the Weekend List! 

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