HomeEntrepreneurship18 Female Entrepreneurs Share Their Biggest Regrets Of the 20s

18 Female Entrepreneurs Share Their Biggest Regrets Of the 20s

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My biggest regret is not going to university.

“At 20, I thought I wanted to be a hairdresser because I wasn’t academic enough for college/university. But I’d always dreamed of being a writer. At 25, I wanted a career change and to go into media. Sadly no one will even reply to your CV if you don’t have a degree, no matter how much life experience you have. At 37, I have worked hard to become a writer, but it’s taken 17 years of working for free and paying for a lot of courses funded by myself. If I had just gone to university got a degree (in anything) I would’ve got a job in media at the age of 25 and not wasted time and money.” – Natalie Dixon


My biggest regret was not taking proper care of myself

“The biggest regret I have from my 20s is not negotiating raises for myself more consistently. I felt so timid about speaking up for myself and always waited for the company I was working for to bring up the subject of a raise. Practicing your negotiation skills is so important because it’s something you’ll be doing for the rest of your life, no matter what career path you take. You are always going to be your best advocate. Fully embrace your worth at your work. Aside from job performance, speaking up for yourself is critical in order to grow at work and financially.” – Alex Beattie


Not following my dreams and starting my business sooner

“My dream has always been to travel the world and make money through blogging and selling my own products. It took me so long to start my business, and by the time I did, I had missed out on many opportunities. 

I was so focused on climbing the corporate ladder and pushed my own dreams aside. I regret not focusing on what I wanted in life and chasing my dreams.

I spent so much time trying to make everyone else happy that I completely forgot about what made me happy Now, I try to do things that make me happy.” – Trysta B


One thing I regret doing in my 20’s is not acknowledging things

I began working in this industry of digital technology when I was 23 years old. My experiences immediately gave me an insight into the gap that exists in the market, particularly in terms of data protection. Technology innovations have been on the rise exponentially, and cybersecurity has become of a lot of significance. This opened my eyes to the potential this industry holds, which is why I started building my business from the vicinity of my parent’s living room. Being a woman in the highly competitive digital technology industry has not been an easy feat.

I regret doing in my 20s not acknowledging the need for a team in that period. When I started the business, I worked in a one-person army; I overlooked the limits of one individual trying to do everything on their own. I believe I wasted some time and hindered the growth of my company without hiring a few people at the very beginning to carry the load with me. I used up a lot of my energy on tasks that could have easily been outsourced or assigned to other members. This would have given me the opportunity to accomplish more of my goals in my 20s.” – Isla Sibanda 


“The one thing that I regret the most is worrying so much about what people thought about me and my crazy experiments and career choices.

Looking back, I feel like I could have started years ago some of my most cool ideas for a business.

Even though some of my ideas wouldn’t have worked, I could have learned huge lessons about money, idea implementation, and how to manage a business with the safety net of my parents’ aid. 

Now I own my business and have a mortgage, and workers is way harder to make crazy decisions. Not impossible, but harder. Today I am slowly working with the concept of Just do it! And I encourage my mentees to do the same.” – Dafhtne Paz


The biggest thing I regret about my 20’s is my misconception about freedom.

“Growing up, and in my early 20’s, I viewed freedom as having a certain amount of money to do whatever with. Money to buy the house you want, the car you want, take the vacations you want, etc. I’ve spent the majority of my life working someone else’s schedule. It took time, but I now realize that freedom is about time more than money. Sure, I need money to pay for bills and my necessities, but time is the true freedom that I seek. I wish I would’ve realized this much sooner!” – Jess Shipwash


Thinking back at my 20s I would say that I took life a little too seriously.

Once you step into your 30s the perspective changes. That is when you actually enter your adult life. I wish someone has told me that. From completing my degree, going to my job, and babysitting I forgot that I was young and I should take some time out for myself. 

“I wouldn’t say I regret working hard in my 20s as that was such a defining moment of my life. That was when I realized that I have to become an independent woman who should not rely on anyone: emotionally or financially. But I wish I had gone to travel with my friends at an exotic spot or hung out at a bar ‘How-I-met-your-mother’ kinda style. 

But whatever I did or didn’t do made me the strong woman I am today; who knows how to handle tough situations in life and who is not intimidated by the men around her.” – Shannon Miller


One thing I regret doing in your 20s is dropping expectations others had of me (family, society, friends) and living life on my own terms, following my gut, not what was expected of me. 

“A quick story about finally doing it – After 10 years in corporate America and in the middle of Covid, I decided to quit listening to everyone else and hit the road looking for adventure. And now, I’m a full-time travel blogger, a citizen of both the US and the EU, and an all-out digital nomad focusing on road trips in Europe. Because of that, I’ve traveled to over 30 countries, half of which have been in Europe the past couple of years. I started my own business. And I’m learning to trust my gut more and more each day. Feels like the 30s are the new 20s.” – Mariana


As a woman and an entrepreneur, there are quite some things I regret doing in my 20s, but the most painful one was selling a business idea that went on to become a big thing.

“As a young tech enthusiast, I had a lot of interesting business ideas, but there was one that always kept me up at night. I worked on this idea day and night without making out time to enjoy other leisure activities. Along the line, I experienced a mental burnout and lost complete interest in the project. When I couldn’t regain interest in furthering the development of that idea, I sold it to someone, and today, that idea is worth millions of dollars now. When I look back, selling that idea is something I strongly regret doing in my 20s. I am still haunted by it.” –  Maria A. McDowell 


As an entrepreneur and most importantly a woman entrepreneur, I believe that young women’s biggest mistake during their 20s is not having enough confidence in their talents and skills.

“In my experience, speaking up in an industry that is dominated by men wasn’t easy and I would miss out on opportunities just because I was afraid to expose myself to criticism. But the truth is that to grow and learn you need to get feedback, and you will only receive it if you share your thoughts. And don’t forget that confidence makes everything sound 100 times better.” – Jess


I regret playing it safe.

“I was a good girl, go to school, get a job. I wish I had been wilder, traveled, dated more, took more risks. Now at 55, I worry that I don’t have time to do all the things I wanted to do when I was young but didn’t do. I tell my 20-year-old daughter to do everything. Don’t even hesitate, pick the scariest thing, and do that thing! We always think we have time to do things later- and some things you can, but it’s not so easy when you have children and responsibilities and a job and your body isn’t as young as your spirit.” – Lewena Bayer


Every penny of your paycheck doesn’t need to be spent.

“While it’s nice to have some money left over each month after paying rent, bills, and other necessities, save that money and start building an emergency fund. Treating yourself to a Starbucks coffee always brightens your day, but that money can be used for a better purpose.”

“You never know what type of emergencies you’ll run into – maybe the car breaks down or a global pandemic will hit, which may potentially result in a drop in income. Having that extra money saved will ensure your rent and groceries are taken care of. You’ll thank your younger self for the financial stability.” – Lillie


One thing I regret doing in my 20s is listening to non-entrepreneurs (who aren’t my core customers) concerning my business. 

“Everyone doesn’t have an entrepreneurial mindset.  It takes a dreamer with ambition and a risk-taker to launch a new business venture. 

A person that has no desire to bet on themselves in that way may not have the ability to uplift an entrepreneur properly without making them doubt themselves.” – Stephanie


My biggest regret is not starting earlier.

“I was too afraid to go out on my own, so I worked for other people until I finally decided to take the leap and work for myself. By the time I started my LLC, I was already well into my thirties. Starting my own business was scary, but it’s been going very well. I only wish I had started sooner. Now I have the flexibility to work with and for people who value my work, not a traditional employer.” – Kate Sortino


One thing I regret doing/not doing in my 20s

“There are a lot of things I regret from my 20s, but if I had to pick just one, it would be not investing in myself and my own education enough. I was so busy chasing after success and trying to build my business that I didn’t take the time to learn new skills or improve on the ones I already had. That’s something that I’ve made a point of doing in my 30s, and it’s made a huge difference in terms of both my career growth and my overall happiness.

I advise others, to make sure it’s investing time and energy into learning and developing yourself as a person. It will pay off big time down the road.” – Kelly Eison


In my 20s, it is a season where everything seems to be trial and error.

“It seems like you just need to try and try and try until you get what you wanted. Of course, there’s nothing wrong with that, most inventions came from that practice, but now as a founder, I see the importance of planning and executing different principles to achieve the goal. I regret trying things without any plans, I think I should be greater by now if I tried to at least look for such information that will help me gain knowledge about a certain thing. Now it is not just you must try but you must also need to be strategic. There must be plans and a budget for every trial to avoid errors. It is a matter of preparedness and the courage to search for adequate information to attain specific goals.” – April Maccario


I regret that in my 20s I focused a lot more on what other people were doing and saying. The competitive nature our culture sets up – for women, especially – is really terrible.

“That framework needs to be shattered: women should stop wasting time and energy judging each other and instead come together and help and support one another. Of course, we’re all human, and growth and wisdom come with age. Now I understand how important it is to uplift other women, and I put energy into that as much as I can, both as a human and a businessperson. I spend way less time worrying about what others are doing and more time enjoying my life and being happy for others when they succeed!” – Lisa Odenweller


One thing I regret not doing during my 20’s? Keeping my life’s balance.

“While you’re still young, it is good to start to achieve your goals in life. Feel guilty when you’re lazy, work hard every single day, yet make sure to spend time for your family, friends, and yourself as well. Earn money from a job that will enhance your skills and knowledge, save money and invest in a business that fits your interests. Do not be afraid to take risks; at first, many errors and trials are there, but you will see that your business is growing as you learn. By that time, you will be able to travel anytime and anywhere, you can spend a night or two in a luxury hotel, and you will be thankful that you started business early.” – Jaya Aiyar

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