If you could go back in time, what would you change? Would you go to a different school? Avoid a fallout with a friend? Maybe you’d take your life in an entirely new direction. Until we master time travel, it’s all hypothetical—but we can still learn from these “what-ifs.” I wanted to explore this age-old question from the perspective of a female entrepreneur, so I asked founders to tell me their primary regret. What mistakes did they make as they launched and grew their businesses? If they could do it all over, what would they change?
Their insights are chock-full of practical advice and words of warning. Pay attention! You don’t want to be the one kicking yourself down the line.
Monica Le Baron, Sleep Coach & Certified Yoga Therapist, Monica Le Baron, LLC:
I regret spending $40K on Yoga Therapy training and other coaching modalities, and naively thinking that clients would line up to buy my services once I completed these certifications. If I could travel back in time, I would have taken longer to finish my training and used this time to generate more sales before investing this huge amount of money. I’m a huge believer in investing in education and coaching, as long as I can afford it and it’s aligned with my business.
Stephania Schirru, Public Relations Strategist & CEO, Dynamically Branded:
Two of the mistakes I made earlier in my career were:
1) Not researching what industry-standard rates were for my profession. I was just so excited to have clients hire me, and I love what I do. But I found out that I was charging about a third of what other PR pros were charging. Now, we charge accordingly and significantly increased our revenue.
2) Public relations is a long game, so you don’t see results right away. Not documenting and sharing the work invested and connections made sometimes had my clients feel dissatisfied. Now, we have very detailed reporting every three months with KPIs. We list every single effort as well as missed opportunities due to clients not providing information, missing interviews and not having marketing assets or products ready on time. We also share results and projects or stories we’re working on right away. This was a game-changer when it comes to customer retention.
Bernadette Saumur, CEO, Talent Matters Inc.:
As a new business owner, you need to juggle a lot of competing interests, including spending a significant amount of time on sales and business development. As my business area is in recruitment and staffing, which is a service, it also meant I had to provide the services myself until I could hire staff.
Knowing what I know now, I would have invested more in technology right from the start. For example, I had boxes of resumes that began to take over my entire basement. Instead, I should have licensed an applicant tracking system right from the get-go allowing resumes to be stored, retrieved and filtered much more efficiently.
Mia Clarke, Owner, InvertPro:
When I started my own business, I felt like I had to wear every hat and do everything on my own. I couldn’t get any help because I thought I couldn’t afford it. I used to spend almost half of my time doing tasks I could’ve avoided by paying other professionals.
What I have learned is that rather than spending your money on different things, you should invest in outsourcing right away. You can hire assistants to do the work that is related to your core business and you can save a lot of time and money instead of doing everything yourself. This will save you a lot of time and money in the long run. And you will have a better chance of getting quality work.
Read Outsourcing: How to Decide, Prioritize and Find Support for Your Business.
Lilit Margaryan, Consultant, Coach & Founder, Mainsail Consultancy:
Starting a business is always scary, especially when you try to start and succeed in a foreign country, like in my case. Fear of failure is one of the strongest emotions. So I started looking for people and organizations who could help me do everything right. I spent a fortune on business registration and 10 times that on my first-year tax preparation.
While the industry norm varies from $99–$150 to register a legal entity and get an EIN as a non-resident alien, I paid $650. After finding a company to take care of my annual tax returns, it cost me $2350 to file and send two reports. A local company quoted $200 with no fee to send an extension request.
So what was my main mistake? I was caught up in the fear of not being able to handle everything myself. I decided to calm my emotions and get rid of this headache by working with the most expensive services—all because of my lack of knowledge. Now whenever I feel lost, I hire experienced consultants and work with coaches to explain the roadmaps and point out the potential traps. Can you imagine how much of my budget has been saved and repurposed to the best of my business since I adopted this simple principle?
If you have any questions or hesitations about what to do or do it or not, it’s always wiser and more cost-beneficial to ask someone who knows instead of trying to find the answers in sales pitchings and open source information.
Lisa Lane, President, Lane Innovations:
As an owner of an e-comm business, we got comfortable ordering from our supplier without double-checking the “golden sample” before shipping. In a quick Zoom meeting, the product performed well and all looked perfect. We were in a rush due to supply chain delays, so we opted to just go ahead and place the purchase order for a significant quantity.
When the product arrived, we found that the instructions inside the box had improper formatting. Lesson learned. Always get the sample in hand before assuming that all is OK. Sometimes dealing with a possible out-of-stock situation is better than dealing with what shows up at the dock!
Deborah Niemann, Owner, Thrifty Homesteader:
The biggest mistake I made was not starting an email list soon enough. I naively thought that people would always continue to come back to me after visiting my website one time, which is not even close to true for 99 percent of your website’s visitors. Getting their name and email address is vital for growing your business. I can only imagine how many thousands of people could have been added to my list. If I could go back in time, I would have put an email collector on my website on day one.
Rachel T. Schromen, Attorney, Schromen Law, LLC:
The biggest mistake I made was not doing my due diligence regarding the networking communities I entered or the business coaching and support that I paid for. Very early on in my career, I attended a conference that purported to be for female entrepreneurs but was really just a high-pressure sales situation that preyed on young entrepreneurs. I ended up paying for a business coaching program without doing any research about the woman leading the coaching.
As it turned out, she was not a successful business owner and has since closed multiple businesses. This mistake was made very early on in my career when I really could not afford business coaching. I wish I had known that it was possible to find genuinely supportive communities of entrepreneurs and hire business coaches who would actually provide value and benefit. I very naively took people I met at face value and didn’t ask questions or do my research!
Margo Fery, Founder, Margo Paige:
My biggest mistake since starting was ordering too many choices for my products. In hindsight, I wish I would have started with a small collection instead of having a full line. When you start a business, you sometimes think, “Oh, this is a great idea, so people will appreciate all the options available to them!”
While the sentiment is true later on, launching and growing takes time for people to find your brand and to gain recognition. My advice would be to start small and gradually build. Don’t overload yourself all at once. You’ll eventually get there and be able to expand, but small steps will lead to a bigger impact in the long run.
Toni Runci, SHRM-CP, PHR, Co-founder & Integrator, BlueLion, LLC:
I started my business in 2018 with my co-founder, Alison. When we started, we thought we had a great trajectory of how we would build our business and scale, all outlined in our business plan. When the pandemic hit, the need for what we do as a business became apparent, and we grew substantially, going from just the two of us to four more employees. Prior to us adding staff and clients faster than we knew what to do with them, we didn’t have a solid foundation of all of our processes and procedures to scale. We had not documented anything, really, on how we managed our day-to-day operations.
When there were only two people running the business, both of us almost always knew what the other was doing. When we grew and added more team members, that became difficult. We needed to trust in the process, but we didn’t really have one. We had to work backward, which was difficult with how quickly we were growing. Imagine adding a second and a third story onto a house as you tear down and repour the foundation. We enlisted our team to support us in this endeavor. We began documenting processes from scratch and holding meetings to review if that was the most efficient way to do it and if we could scale it from a few clients to over 100.
This impacted client satisfaction. Clients felt the bumps and bruises of us finding our way, and as a small growing company, bad word of mouth could create issues for long-term success. This also gave us the sense of always chasing our tails—offering credits to unhappy customers and lowering our prices to “match” the level of service we felt we were giving.
If we could go back in time, I would write down everything and make a process for everything, even things that seem so mundane. As an entrepreneur who often manages everything, you’ll eventually need to offload tasks by hiring someone internally or outsourcing it. If you hire someone in-house, having a document to train with and then update and modify is much easier than trying to create the wheel when the wagon is already going a million miles an hour. Having this foundation and structure in place would have allowed us to grow quicker and more sustainably with less stress. It also would have reaped better financial rewards if we were always able to deliver the high quality we were building our brand on.
Jessi Burg, Founder, Outgrow Your Garage:
During the beginning stages of my previous landscaping business, I hired my sister-in-law to do receipt scanning. Her position gradually grew to include more financial and administrative responsibilities in conjunction with what the business needed, but I didn’t do a very good job of making sure she was meeting all of my expectations. I really shied away from those important conversations because she was my sister-in-law.
On top of that, she wasn’t asking for help with what she needed, and she didn’t tell me when things started to get messy financially. Once our internal processes became chaotic, there was no going back. I realized too late that I had someone in a key position who didn’t understand her position and didn’t fit in with our mission. This resulted in a lot of wasted time in terms of improper estimates and key information not being relayed accurately to field staff. Since I was so busy with the fieldwork and estimates, I wasn’t fully aware that my point person was struggling and things were falling apart. She became frustrated with her work situation and started bad-mouthing me behind my back, which really brought down company morale.
I didn’t have enough oversight to get things done. I should have set very clear metrics and expectations, and I didn’t. Instead, I should have made it very clear what I was willing to teach the point person and what they were expected to learn on their own.
Some of the problem was with me as a manager. I learned a lot about how to delegate and also about fit—how does who I’m hiring actually fit into a position? Hiring family members can get very messy without clearly set metrics and expectations, and I was hesitant to talk to her or fire her like a regular employee because she was a part of the family. If I had taken control of things or fired her a lot sooner, it may have saved my business.
Marina Vaamonde, Owner & Founder, HouseCashin
My biggest regret was when I failed to do my due diligence on an investor for my company. I made the mistake of thinking that the only thing that an investor does is give you money and then move out of the way to let me do my thing.
I was very wrong. Investors come in many different shapes and sizes. Some are very active and want to essentially run the company for you, while with other investors, the only contact they want to have with you is to give you the money and then receive their money once you’re profitable.
Again, the key mistake I made was not learning what type of investor I was dealing with. I think I made this mistake because I was aware of how few female founders receive investment and how much the playing field is slanted in favor of male entrepreneurs. I was simply happy to have an investor interested in my company at all.
My advice to other female entrepreneurs is to not be too desperate for investors. Do your homework on investors and make sure they align with your mission, values and how you operate your business. Don’t be afraid to step away and say no, because sometimes the cost of receiving money is greater than the cost of not getting any investment.
Heather Remec, Owner, SalesSong Studios
My biggest mistake in business has to do with expectations and contracts. Early on in business, I was clear about what would be delivered when it came to checking things off a list, which is helpful to both parties. What I wasn’t clear about was how many rounds of edits were included!
I worked with a particular client years ago. We did a rebrand and built out her website and marketing process. She was an older woman (retiree age) and wanted to bring new life to a business her deceased husband and herself had created.
As we began working on the rebrand, there was a lot of resistance. We knew the old brand wasn’t working for obvious reasons, but everything she said she liked ended up not being ‘the one’ after a day or two of thinking about it. And, because the contract and agreement didn’t state how many rounds of edits or new options were included, we ended up creating over 40 logos to keep our promise of delivering on the service.
Throughout the project, I came to realize the resistance wasn’t in our work… it was in fact that while she knew these changes were needed, she felt she was losing parts of the brand she and her husband built. She was still in mourning and didn’t want to let anything go.
From a business aspect, being clear with expectations and limits inside of the contract could have saved us a lot of time, money and energy. And, from a personal perspective, people are people, and it sometimes takes working together to realize where resistance to change is coming from.
Kathryn Bernell, Founder & CEO, reHarvest Provisions
When we were gearing up for our ‘big national rollout’ in 2020, I had all my eggs in one basket in terms of distribution channels. We were all-in on foodservice for hotels, offices, gyms and college campuses. We were focused, which I do think is an important part of growing anything early-on, but we weren’t diversified. COVID hit, and within 48 hours, my entire business crumbled.
I had to scramble to rebuild our business from the ground up. It was painful.
The biggest regret? Putting all my eggs in one basket. There was zero diversification. Someone much wiser than me shared their experience building a business. They told me you should never rely on more than 25 percent of your supply chain, your distribution or your revenue from one single source. If you lose 25 percent of any bucket, you can recover. Staying focused is critical, but making sure that you have mapped out and built in ways into different verticals is key when you risk the growth of anything you are scaling.
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