9 Creative Entrepreneurs Share Their Business Struggles + How They Got Past Them

If you’re in the beginning stages of your creative business, today’s post is for you.

The beginning can feel like a mountain that you’ll never be able to climb. That insurmountable feeling is normal. We’ve all been there. We’ve all felt the prickles of doubt.

That’s why I asked a group of creative entrepreneurs that I respect to share the answer to this question:

In the beginning stages of your creative business, what was your biggest struggle? How did you move past it?

And, here are their answers:

Michelle Ward

In the beginning stages of my business, my biggest struggle was my full-time job! I knew I couldn’t cut off my income stream and strike out on my own before (a) I was certified as a life coach (b) had some savings in the bank to live on so I wouldn’t have to execute Plan B (something like working retail/waiting tables) for a good 6 months (c) I felt confident that people in the world knew I existed.

The first thing I did was to get out of my full-time job that expected me to be on my BlackBerry 24/7, had me travel way too much for my liking, and came with a verbally abusive boss (fun!). Before even signing up for life coaching classes, I made it my mission to find a non-Blackberry, non-traveling, overtime-free job with a boss who wasn’t psychotic. I met with what must’ve been close to a dozen recruiters to rework my resume, test myself on computer basics, and have ’em set-up interviews for me. In a month or two’s time I had a job offer to be an Executive Assistant in a financial consulting company. It wasn’t the best fit ever, but it had all the requirements I was looking for, gave me a bigger salary (and a bonus! and overtime pay, if I had to work it!), as well as the guarantee that I could devote my nights and weekends to my coaching classes and clients. It took me 2 years & 7 months to go from my first day there (which was also the first month I started my life coaching classes!) to go from my first day to my last, but who the heck’s counting now?! I’ve been a full-time entrepreneur for over 13 months and am thriving, and my full-time, abusive-free day job helped me get here.

Jess Van Den

I’d have to say that my biggest struggle was time management. That is – working myself so hard that I would reach burnout. This happened to me once or twice during the first year, and I really had to make a promise to myself (and my husband!) that I would take at LEAST one day off a week. (Well, by take a day off I mean no work after checking and dealing with e-mails in the morning, and again in the evening!)

Taking a little bit of time to unwind – whether we go out, or I read a novel… or, wonder-of-wonders!, I craft something just for fun – just taking that little bit of down-time is vital to keeping my creative energy going.

If you don’t take a little time out, it’s easy to spread yourself too thin, and end up hating your work because it’s all you are doing. The time away from your work is vital to keeping your work vibrant!

Jessica Swift

In the beginning stages of my creative business, my biggest struggle was trusting that I was going to make enough money every month to get by. The struggle wasn’t actually money, because I always seemed to make enough and have enough, but the TRUSTING that the money would be there. That’s an important distinction for me. I’ve been a worrier my whole life, so the worrying part of my brain quickly glommed onto the “what ifs” about not having a steady income, even though in reality I was doing just fine.

I do have to say, this is still my biggest struggle in my business. Sometimes I let money worries take over, I think just out of habit. I’ve never not had enough money, and I have no reason to believe that I’ll ever be in that position, but old habits are easy to fall back on. Over the years I’ve slowly moved past pieces of this struggle– for example, I don’t worry anymore that I won’t make enough money every month. My worry has sort-of transformed into “what if I don’t make enough money to live the kind of life that I want to live?” It’s a worry of never having enough, which is an illusion that I’ve completely made up in my head. The way that I’m able to move past it is to realize that RIGHT NOW, in this moment, I have enough, I am enough, and that there’s nothing to worry about. Having faith and moving forward despite being worried and scared has been my biggest antidote to struggle in my creative business, and I imagine it always will be! Action cures fear and struggle.

Mayi Carles

One of my biggest struggles starting out was figuring out the rules of the game, particularly the unspoken etiquettes. Was it alright to utilize other peoples images? Was it cool to submit my work to big name blogs? So many questions marks. I still don’t have all the A’s to my Q’s, but I’ve learned a very important lesson: “When in doubt, it never hurts to ask.” This mantra sure helps me sleep at night.


Zoe Rooney

My biggest struggle at the beginning (and ongoing, it truly never completely goes away) was to figure out what I love to do and give myself permission to spend my time doing it. I mean, you always hear “do what you love,” but what about when you aren’t quite sure what you love, or you love a lot of things? Does it become “do what you love most”? Or maybe “do what you love that also makes money”? Or some hybrid? One of the best tips I’ve heard, and forgive me because I can’t remember where it’s from, was to think about what you gravitate towards but feel you “aren’t allowed” to do (maybe the things you do when you’re “supposed” to be doing “work”) and go in that direction. For me, I felt like focusing on hand-embroidery for my paper goods was risky because it’s hard to scale up production. But, I really deeply love the result, the process, the IDEA of threads woven with paper, so I’m going with it (and raising my prices accordingly).

Laura Simms

Before opening my biz, I agonized over pricing my services.

It was so exhilarating to think that I would get paid for doing this work. I had worked with clients for free, so I felt confident about my abilities and the value clients got. But attaching a number to all that was intimidating.

So, I did a lot of research. I wanted to know what my “competition” was charging and how they were bundling their services. This was important research to do, but at a certain point, it stopped being useful and became an avoidance tactic.

My head swimming with what everyone else was doing, I had the bright idea to consider what numbers I felt good about. Ones that made me proud. I scratched out a lot of figures on paper, and found the ones that were Baby Bear sized–not too big, not too small. This was intuitive. This was getting easier.

Then I imagined my ideal clients, their finances, and priorities. I wanted the cost of working with me to pinch a little, but not be prohibitive. Hmmm. These numbers were aligned with my Baby Bear numbers. I had found a sweet spot.

What have I left out of the story? A lot of hemming and hawing and distress over this whole process.

What I’ve learned: You can always change your mind! It’s your business, so adjust to make it work for you and your clients or buyers. The most important thing is to get started and let your business (not your imagination) inform your decisions.

April Bern

In the beginning stages of my creative business, my biggest struggle was with myself! Self-doubt was definitely my biggest hurdle. I was so worried that no one would like my photography or my paintings, and that no one would want to spend their hard-earned money to buy them. I remember telling my boyfriend, during one particularly bad self-doubting episode, that everyone and their brother owned a digital camera, why would they want to buy my photos? Why bother? He said something that has stuck with me to this day. He said “So what!? Everyone might own a digital camera, but no one else owns your vision, your thoughts, or your ideas.  That’s what people want.”

Support and encouragement from my friends and family really helped me work through my periods of self doubt in the beginning stages of my creative business. I still have those moments and thoughts periodically and when that happens, I look back at my past experience and know if I just do it (whatever it is that I’m worried, or doubtful about)  that I will be happy and things will work out. People can’t find you or your products if you don’t put yourself out there!

Leah Shaver

The thing that we are all prepared to struggle with when we start our creative businesses is finding clients/making sales. That’s pretty par for the course, right? It’s expected that it will take some time to gain that momentum. I struggled with this for awhile, but very quickly felt like clients were just falling out of the sky. I was very fortunate in this regard. The REAL struggle for me was extremely related, though: the fear that my business would collapse if I took any time off. I didn’t take a day off for the first ten months after starting my business. I even went on a “vacation” to Florida in which I sat out on the lanai with my laptop for the vast majority of the week.
Ten months after starting my business, my live-in boyfriend and I ended our relationship and he moved out. I realized then that I was trading my relationships with friends and loved ones — my life, really — for my business. Things changed pretty quickly as a result. I stopped working at 6pm. I stopped being available for clients on weekends.

I continue to struggle with this. I love my business, so the line between my business and my life is very blurry — but it’s an important one. I’m fortunate at this point that I’m single and childless and can go through phases where I’m very focused and selfish with my time. But for the vast majority of us creative entrepreneurs, this isn’t the case. Regardless of who needs your attention, I urge all of us to remember that we’re real people who deserve a high quality of life. I think it’s really important to pick at least one day of the week to shut down the computer, put your work aside, and go outside and play.

April Bowles-Olin

Of course, I thought it was only fair if I also added my answer to this question.

The biggest struggle I faced in the beginning stages of my business was getting past my “everything has to be perfect right freaking now” mentality. I got discouraged and overwhelmed, because everything wasn’t how I wanted it. And, each time I turned around there was something else I needed to add to my to-do list.

I got past this struggle by continuously reminding myself that this was going to be a long journey and that I should enjoy each step of it instead of getting uptight. I broke up big goals into small tasks, and worked on one thing at a time. Instead of getting overwhelmed by the big picture, I concentrated on one small to-do item at a time.


30 Responses to 9 Creative Entrepreneurs Share Their Business Struggles + How They Got Past Them

  1. Kristy May 4, 2011 at 8:05 am #

    Its so wonderful to hear that other entrepreneurs get the same types of anxiety that I know I’ve had
    Kristy recently posted..Tea for Two!

    • April May 5, 2011 at 7:55 am #

      Glad you found the post helpful Kristy! We definitely all have anxieties 🙂

  2. Patty May 4, 2011 at 8:25 am #

    So much good stuff here! Need to reread to digest everything. Thanks for gathering this awesome group of ladies together.
    Patty recently posted..Taking the Heartsy Plunge

    • April May 5, 2011 at 7:56 am #

      You’re welcome Patty! They are a great group, right?

  3. Stacy May 4, 2011 at 8:29 am #

    Fantastic to read these! I especially found myself nodding at the people who struggle with taking time off. I LOVED what Leah said: “I love my business, so the line between my business and my life is very blurry.” That is exactly how I feel, and it’s been only in the past couple of weeks that I’ve really committed myself to taking one day off per week (prior to that, I’d taken three days off in the past two months). I honestly do miss working a bit on my day off, which sounds demented, but having that day to recharge really is a great feeling. And then when my new week starts, I’m extra excited about getting back to work. 🙂
    Stacy recently posted..Romance – Cream- bronze- vintage rose Swarovksi crystal and pearl earrings

    • April May 5, 2011 at 7:58 am #

      I know exactly how you feel Stacy. For about the first 5 months of Blacksburg Belle, I worked nonstop. My husband had to finally say, “You need to take time off.” I definitely have a hard time staying away on my days off–but like you, I feel recharged each time I do.

  4. Kylie May 4, 2011 at 10:29 am #

    This was great to read, April. Of course we all know that our colleagues struggle too, but it’s empowering to hear it directly from them and then see what they’ve done to kindly work with themselves. Thanks for bringing these wise voices together!

    • April May 5, 2011 at 7:59 am #

      Glad you enjoyed it Kylie!

  5. Rachel May 4, 2011 at 10:32 am #

    I agree. All of this is incredibly helpful to hear, and many of these things strike a chord with my [currently still limited] experience. It’s interesting how a lot of the doubts we have are reasonable (can I pay the bills? etc.), but even though practical considerations are a totally valid thing to have on your mind, it’s a small step from letting them rule you and cripple you to letting them empower you. It seems to me that each of these ladies made a decision of faith somewhere along the line, to believe in their own inherent worth and the worth of what they are doing, and to move forward, letting those fears push them to excel.

    • Zoe | A Quick Study May 4, 2011 at 1:16 pm #

      Rachel, I love what you’re saying about practical considerations ARE important but how they aren’t MOST important. It’s all about taking those considerations and figuring out how to make them happen while still doing what feels right.

      Thanks, April, for putting this together! I loved thinking about the question and it is so affirming to see all these answers together.
      Zoe | A Quick Study recently posted..Time is short presentation matters!

      • April May 5, 2011 at 8:01 am #

        Hey Rachel,

        I agree that it seems you have to have faith in what you’re doing and believe in it’s worth. That’s definitely a thread with many of these women.

        Hey Zoe,

        It was so fun collecting all the answers! And, I think it’s really helpful to see how we all struggle and overcome it.

  6. Erin May 4, 2011 at 2:45 pm #

    Thanks so much for this! I can’t seem to get enough of reading advice from fellow small business owners and I found this collection especially helpful because everyone described specific problems and, more importantly, solutions. Generalizations are no help to me. Plus, it’s always comforting to hear I’m not alone in the things that most overwhelm me in my business… self-doubt, perfectionism, competition and time management.

    • April May 5, 2011 at 8:06 am #

      You’re welcome Erin! I’m so glad that you found this post helpful.

  7. Danielle May 4, 2011 at 2:53 pm #

    This was such an informative post. Its difficult to remember that successsful people once were newbies & had the same struggles/obstacles/self-doubt that everyone has. I found myself relating to almost everything that was said & I appreciate everyone’s honesty & advice. Great post!!!

    • April May 5, 2011 at 8:08 am #

      We’re definitely all human, have doubts, and struggle. I’m glad you could relate to it 🙂

  8. Jessika (Oh My Handmade) May 4, 2011 at 6:26 pm #

    Such beautiful faces & stories! Thank you April for bringing these lovely women together to share their thoughts. I took something away from everyone’s answers & can identify with so many of them! Bookmarked this one as something to visit again & refer others to: )

    • April May 5, 2011 at 8:10 am #

      Yay Jessika! I also took something away from every answer. It was such a fun post to put together 🙂

  9. Jennifer May 4, 2011 at 8:59 pm #

    thanks April. after reading all those gorgeous girl’s stories I am feeling quite normal … well relatively normal. lol. thank you so much for posting.

    • April May 5, 2011 at 8:13 am #

      You’re so welcome Jennifer. It’s comforting to know that we all struggle with this stuff.

  10. Aileen May 6, 2011 at 4:29 am #

    Wow! Awesome, awesome, awesome! I needed to read those stories right now.. I can relate to something in everyone of them and it’s given me a few confirmations & made me realise how I’m not alone with the time management struggle.. I’m loving every minute of my new biz & every minute of my family and now I’m going to try and sneak a minute for me too .. like I know I should have been 🙂

  11. Virginia May 6, 2011 at 9:32 am #

    I’m just getting started and feel like I am struggling with doubt, pricing, and the perfectionist problem. I finally just had to “go for it” and list some things to get started. Now I’m at the point of finding my ideal customers. I feel like I’m connecting on my blog, but how do you find your customer if they’re not necessarily blog readers? Or do I stick with that? Too many questions, too little time 😉 Thanks for sharing everyone. It’s nice to look up and learn from all of you!
    Virginia recently posted..Mothers Day Illuminate Linkup

  12. Gabriela Frederick December 9, 2011 at 2:30 am #

    It seems to me that each of these ladies made a decision of faith somewhere along the line, to believe in their own inherent worth and the worth of what they are doing, and to move forward, letting those fears push them to excel. For about the first 5 months of Blacksburg Belle, I worked nonstop.
    Gabriela Frederick recently posted..Acne Tips

  13. Ninette February 9, 2012 at 7:25 pm #

    WOW!! I love this! Thank you so much for asking these brave and amazing women to share their thoughts. I too am in a transitioning stage in my career. I have been a professional aerialist with my own production company for the last 12 years and now that I am out of a 20 year marriage I have been drawn toward a professional body building career and starting my own women’s accessory line called HipShrug. this last 6 months has been a real test to my inner world and my old beliefs of money and worthiness. Its having to really trust in the Universe and say “ok I’m here and I’m so drawn to do this. I have to truly trust that I am supported and will be guided along this journey.” I am starting to see how this time is an opportunity to really look these fears straight on and work thru them so that later down the road I can have a clearer path to my vision and know I am worthy of that! I wish you all the best in your desires and manifesting your dreams. Thanks for the inspiration! Much needed at this time!

  14. Darren Heslip September 6, 2015 at 2:01 am #

    Great post! Seems as though we all go through the same sort of struggles. I’ve been through most of those but when my actual break through happened,

    it was the moment I finally understood what “taking massive action” meant. It was like an awakening.

    Thanks for the great inspiration!
    Darren Heslip recently posted..What iPAS2 Can Do For You


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