Freelancers who start businesses doing what they love are some of the most heart-centered entrepreneurs on the planet.
Not only do they truly love and benefit from practicing their craft or delivering their gifts, others feel it and want to be around that energy. Customers are naturally attracted, like moths to a flame.
But heart-centered entrepreneurs can be a bit starry-eyed about their core business at their own expense.
They get swept up in perfecting their thing, and set themselves up for some unique pitfalls. Because they love their craft so much, they forget the business. Their more dispassionate colleagues avoid these things.
I’m not telling you to suppress your emotions or enthusiasm. If you’re fired up about building your dream by going into business with a hobby or interest, go for it! The world needs more passionate people like you. But take it from someone who has made every one of the following mistakes, it’s so worth checking these boxes. You’ll feel better about your work, and be able to serve customers better, too.
1. Forgetting the legal stuff.
Helping people accomplish their dreams through your gifts is a heady feeling — almost like being in love. But don’t forget contracts and milestones. Once, I lost a month’s work by digging into a project a little too much enthusiasm, but no real commitment from the client. You can imagine the result. No payment from the client, and my copywriter/marketer’s broken heart. (I had invested more than time and energy than my client. I invested my heart and mind.) I put everything in to a job that really had no future because the client was not invested… and I never got paid. Now, contracts make me feel more comfortable and excited to move ahead.
2. Falling behind on your books.
Book keeping is right up there with the legal concerns. I used to avoid book keeping whenever possible. But it’s just not possible to ignore it forever. The longer you let things slide, the more work it takes to get your books in ship shape again. If you’re like me and would rather poke a dull ice pick into your eye than file things and keep records, then get someone very competent to do this for you.
The trick is being patient and diligent as you set up your books. You have to participate in the process up front if you want it done right — and if you want your book keeper to be able to work without you in the future. It’s worth the time and the bloodshed involved when, for example, you have to re-file your taxes because the records sent to your accountant turned out to be wrong, as I experienced not too long ago. “Trust but verify” comes to mind here. Take it from me. Make a date with your money and stick to it.
3. Underestimating the importance of being profitable.
If it’s a hobby you love, perhaps you’ve been doing it on your own free time; or in service to an organization or client; or on a volunteer basis. (As an example, I started writing copy for charities and schools.)
You finally decide to hang out your shingle, and serve your clients. Now make sure that you are charging more than you make. Otherwise you will not be in business for long.
If you’re like many heart-centered entrepreneurs, you’re tempted to give away or barter your gifts. Don’t do it. Every time you give it away, you devalue your gift and make it more difficult to internalize and own the energy of prosperity that is rightfully yours. Just because you love it doesn’t mean you can’t charge what you’re worth.
Remember, you’re in business to make money.
4. Not getting the help you need.
I know very few floral designers who love HTML, nor fitness trainers who love creating e-newsletters. At first, you may have to create some marketing or IT pieces going on your own, but as soon as possible you must get assistance with the tasks you hate the most.
Three reasons for this:
- Bad energy: Doing crap you dislike drains you and prevents you from wanting to keep at your business.
- Time suck: Handing over work that others can do better frees you to leverage your real talents and save precious time.
- Blocked resources: Someone out there can do it way better than you. I had to admit I’m not great at graphic design, even though I know good design when I see it. It was worth every penny to let an expert take over my latest website and logo redesign.
5. Lack of self discipline.
Yoo hoo, all you work-from-home entrepreneurs… The endless distractions can easily derail your intentions. A key ingredient of a great entrepreneur is someone who can focus on what needs to be done first to move them forward the farthest.
Whether that means focusing on time management, or discerning next best steps, strengthening this muscle will set you apart from every other wannabe business owner. If you don’t get a handle on setting goals and taking steps to achieve them, you will be like most of the small businesses that fail in the first five years.
You will make no progress and you will give up.
There have been months in that past when I put a hundred other things before my copywriting business…my family, my workouts, shopping, housecleaning, cooking… I’ve begun to integrate the important stuff (family and workouts) and just do the rest of it when my energy is not at its highest level.
Now, for example, even though the HEB market is least busy during weekday mornings, I use this precious time to write, not to get groceries. Mornings are power hours for writing and exercising — the most important activities of my day, and the ones that propel my business forward.
As soon as I understood that in my bones, and made a pact with myself to keep that time sacred, my business started to move ahead. I can always shop, and battle the crowds later!
6. Isolation.
If what you love doing most is a social thing, or if you work with people directly, then you’re probably doing OK here. For businesses like writing, graphic design, jewelry creating, or app design; working in solitude (though often necessary) can deplete our best resources.
People are what make your business profitable. Bottom line. They are your customers and colleagues and they shoot your business ahead the more you get your work and gifts “out there.”
My business mentor Lisa Sasevich frequently says “Showing up matters.” Since working with her, I’ve learned to make myself presentable and to take my place at the table.
Community is the key to happiness and success.
Another great friend, Amy Cole, the LinkedIn expert in my circle, suggested I join BNI and show up weekly. Since doing that, I’ve become more clear about how to serve other small businesses and make my network more profitable.
Flying solo from behind your computer, or in your own private workshop is necessary for many heart-centered entrepreneurs. However, a thriving business requires that you make time to get out of your comfort zone and mingle with people. That’s what it means to work “ON” your business rather than “IN” your business. You must practice networking at least 10% of your time in order to grow.
7. The love for your craft dies and you feel like quitting.
Agh, this one hurts. It happens, though, so you’re smart to be on the lookout for it.
Here’s your first clue. Your heart starts looking around for something new to love. What previously gave you joy has now become “work” and so you start slacking off looking for a new fulfilling activity.
This happens a lot with creative types. I should know. I used to love the fiber arts until I realized I didn’t know how to make things out of fabric, build a business around it, and still love it. Making a doll, a purse, or a fiber journal stopped being fun because it stopped being my hobby. Uh oh.
Lesson learned. I still play with fiber and fabric, but I do it because I need the downtime and the open creativity. Same with my art journals. I love creating art, but I found I did not love the business of creating art. Huge difference!
It helps to rub shoulders with people who are doing what you love to do, in order to keep your audience engaged and interested.
8. Lack of marketing strategy.
Now, this may sound harsh, but I love you, so I’m gonna say it. I’m the first to stand up for the tiniest of micro-niches out there. If you love making dollhouses out of playing cards, then I truly believe you can build a business out of it, and even gain a decent following. But it’s going to take some time and some effort in marketing your dream.
Here’s where your passion serves you. You love it, so your enthusiasm and your personality will be the center you work from.
It may take a little while, but steady efforts to grow your community will eventually pay off — if you spend time marketing yourself and your product.
Another requirement is market research, even for a small business. Sometimes I meet entrepreneurs who have a great idea, but they don’t know who their market is, or what drives them. Invest the time to understand your ideal customer. If you make water bottles, understand if your customer is drinking water from it on the subway, or on a hike in the mountains. Know why they want to own a special water bottle (e.e. is it the design, or the function?) and what they see is the primary benefit.
Test things. As you build the business you love from the hobby or product you love, get it out there in front of potential customers before you invest a lot of money in advertising or production. Daymond John from Shark Tank says if you can sell 50 items from the back of your van in the parking lot of a mall in two hours, then call him. He wants to talk to you!
9. Endless tinkering.
Here’s when you know you have a problem. Your numbers and goals are less important than the enjoyment of the work. If you are lucky enough to build up a business from that thing you absolutely love doing, AND your market sustains a regular income, you may be very happy to simply coast along with no growth, testing new things and expecting a loyal customer base to keep things going. But, if you are struggling so much that you’re thinking of moonlighting as a barista at the coffee bar to fund your business, you may have to rethink your business.
I know you love it. That’s great. But there is a little mindset shift that has to take place when you go into business. You can’t love it so much that you tinker, or tweak every little thing. You can’t expect customers to tolerate the intricacies you adore about your art, craft, service, or hobby. Sure, set aside time to experiment with new techniques, but at some point you have to go fast and far with what you know and what you’ve already mastered.
The key is to pick one thing that’s working and keep drilling down into those results. Practice getting better at conversion in those channels.
Document what you know and set goals for growth. Dig in to the business and every now and then stand apart from your “love” and observe it with a critical eye. Tell yourself it’s nothing personal. It’s only business.

10. Neglecting scalability.
This goes hand-in-hand with that common demon heart-centered entrepreneurs battle often…they say YES to everything. They take every one-off job (who would refuse new business?) and try to make each and every customer happy by catering to individual requests.
Sadly, it’s a no-win situation. Repeatability and systems will set you free to love not only your passionate hobby, but also to love the business you are trying to build.
You can still swoon over traditional Bohemian cooking, coffee roasting, or blending things in a Blendtec. You can start a business doing anything your heart desires these days, so follow your heart…and take account of these ten mistakes.
Is there a pitfall you’ve experienced that I didn’t mention? Please share. Comments always welcome.
Need help making sure you’re targeting the right new customers for your business? I help freelancing business owners just like you. Set up a time to chat.