Five key business mistakes I have made in my years of self-employment

common business mistakes

Ready? Here are five key business mistakes I have made over the years that I wish I had done differently… This is how we learn, right? We make mistakes. Ideally, we learn from them. I’m doing this in the name of showing that we are all on a learning path, that where we are right now on our business is not where we’ll be a year from now, let alone five years from now.

May these serve as cautionary tales for you. Some, I will admit, I still haven’t really dealt with (see mistake #1: Logo).

NO PROFESSIONAL LOGO

To this day, over my 20+ years of self-employment, I’ve never had a professional logo design for myself.  For over a decade I owned a childbirth education and doula agency. The logo was… haphazard. It began as a simple line drawing I made for myself, but the image quality was questionable and my font choices… horrible.

Then I found a gorgeous needlepoint image that meant a lot to me and got permission from the artist to turn it into a graphic image. That sounds good, right? Unfortunately, it was WAY too complex an image to serve as a memorable logo, and while the image held great symbolism for me, it didn’t speak to my target market at all.

UPDATE:  That original logo is no longer there!  I finally bit the bullet & created a logo that feels far more like me! That’s what you can see now in the top left corner of the site.  Below is a logo before & after comparison. I’m so much happier now!

Do you need a professional logo?  Obviously, I have thrived for 20+ years without one, so it is in no way a make-or-break aspect of your business success. In fact, many of my clients (especially those just starting out in their business) choose to skip a logo altogether and simply have me write their business name in our chosen site font. It is definitely a business element that you can add in when you are ready. Or perhaps never do at all.

So why do a logo? Well, a gorgeous logo can go a long way to promoting your brand vibe and professionalism to potential clients. Here are some common logo design mistakes to help you come up with your best logo concept. need help with a logo? Check out my design partner My Business Solutions for logo help.

NO BUSINESS PLAN

I am a deeply intuitive business owner. I have flashes of inspiration and can come up with new business models & offerings and bring them to life the very same day. That’s just how I roll… Unfortunately, in the past I rarely took the time to truly analyze the viability of these inspirations. Sometimes they were a wild success, and sometimes… not so much. I’m ok with that, but in recent years I have gotten a LOT better at doing my research.

While planning spreadsheets with financial projections & marketing plans are not my happy place, they do give really helpful information – and have helped me make wiser business decisions than I might have done. My intuition is still my #1 guide in growing my business as The Website Doula, but I’m pleased to say that I have learned to appreciate having a bit more of a foundation before I take a leap in a new direction!

SAYING YES TOO OFTEN

Why do we do it? Part of it I think is just one of the underbelly aspects of self-employment. Saying yes to clients is what creates regular, consistent income – and because we don’t know when the next awesome client will emerge, sometimes we say yes out of a scarcity mindset rather than trusting that the right client will show up.

The result? A client that truly isn’t the right fit. A project that I don’t enjoy doing. Time used on that client that could have been invested in attracting the right clients. I’ve gotten much, much better at saying “no” over the years, and what a difference it has made!

NO PROFESSIONAL PHOTOS

This key business mistake applies to both headshots & photos of me in action with clients. I see this issue ALL THE TIME on holistic practitioner websites. Junky stock photos, dated photos, photos with the other person cropped out, photos that are too small that have been enlarged and look just plain horrible.

It took me YEARS to say yes to a professional photoshoot! My excuse? I had a bunch of them… I didn’t like the way I looked in photos. Weight gain from my children, skin irritation from pregnancies, lack of $ to invest. The list goes on… Plus all the logistics of coordinating with clients for a photoshoot simply gave me a headache.

A few amazing photos – both of you on your own and in action with clients – can go a LONG way to making your social media presence & website feel approachable and professional. I am fortunate to now have my older son minoring in Fine Arts / Photography in university so am sure to do a photoshoot every time he comes home for a visit. In fact, we have one booked for next week!

NOT ASKING FOR HELP

This has been a HUGE learning journey for me over the years. As you might have gathered from the business mistakes above, I am a devoted DIY-er type. I go to craft shows and think “Hey, I could make that myself”. I look at restaurant menus and opt to stay home & cook it myself. I look at gorgeous clothing and think “Hey, I could sew that.”

A lot of my clients have a strong DIY ethos as well, often reaching out to me only after they tried building their own site and ended up only feeling frustrated. (if this is you, be sure to check out my free doula web design resources!) Like so many of you, I have spent untold hours of my life as a self-employed business owner doing tasks that could have been better done by someone who actually knows what they are doing. My #1 issue? Bookkeeping. I am SO thrilled to finally have a bookkeeper who takes care of all the tracking for me.

I also now have a VA (Virtual Assistant) who rocks my world. She has been masterful at prompting me to ask for help and let go of tasks that I really don’t need to be doing. Finally, I have learned to say yes to business coaching to help me make the most of my business & plan for growth.


There’s a lovely song by Ben Platt titled “We grow as we go.” While he is singing about lost love, the line “We’ll grow as we go” strikes me as relevant as I write this post. It’s ok to grow as we go. It’s just fine to make mistakes. As long as we keep learning. Thank you for trusting me as your Website Doula to accompany you in your growth journey.