Lately, I’ve been thinking about all the trials and tribulations I’ve gone through as an employee and entrepreneur and someone who went straight into the startup landscape without a ton of equipment on me. A guy I worked with at one of the previous companies told me about “free soloing,” and I’d say that’s the best way to sum up my career.

top 10 entrepreneur mistakes in business

I’ve been climbing mountains without much backup or help, but I finally opened up my circle. I’ve allowed others to come in, give me advice, and to continue to climb these metaphorical mountains. I’ve learned to accept that sometimes you can’t do everything independently and will need a helping hand. Here are all the things I’d tell my younger self to avoid the mistakes I made as an entrepreneur.

1. Take More Time Off from Work!

Back when I worked at one of my earlier jobs, I would grind constantly to the point where the only days off I’d take were to get my wisdom teeth removed. That’s it. Otherwise, I was working and coming into the office early. Sometimes, I wouldn’t get out of there until 6 p.m., and then have tons of traffic to deal with coming home. I worked so much that I got myself into a fender bender in 2017, hitting a USPS truck. It’s a humiliating moment I still look back on years later, but it was a major sign to me to slow down and to take things easy!

Whenever you have PTO available, use those days to your advantage. Don’t let them fall by the wayside. They are there for a reason. Companies know that you’ll perform better if you occasionally take breaks and travel places to enrich your mind.

2. Don’t Talk Too Much About Your Personal Life

Here’s another dumb mistake I made in the past as an entrepreneur. I’d tell my coworkers about things that would go on in my life. It would never get too personal, but looking back, I think it would have been even easier to get along with them, keeping those details to a minimum. Thankfully, at my previous job, it wasn’t the case, and I was able to get along with nearly everyone and work together on a common goal. It’s just something that would have saved me lots of time and stress had I known this earlier.

3. Learn More About the People You’ll Work With

How many times have you found yourself in this situation before? You meet someone online or in real life who says they have your best interests. Only for their actions to say otherwise. Yeah, I’ve been in that situation too many times before and it’s never ended well. Know your self-worth and don’t let anyone tell you what you need to do unless they are legitimately giving you constructive advice. Otherwise, it’s likely a ruse for said people to take advantage of you, profit off your contributions or try to screw you later in many other ways.

Only work with people you know personally in real life, and even then, be careful too. When it comes to business partnerships, you’ll quickly find out these “friends” might be wolves in sheep’s clothing or get greedy and impulsive. The last thing you need as an entrepreneur is to have toxic influences or people in your life! Know when to spot a rat and kick them to the curb.

4. Failure is Okay As Long As You Learn

It’s okay to make mistakes and fail every so often. What’s not okay is to continue to repeat the same mistakes. Employers can be forgiving to a point but if you’re not getting it, it’s understandable why they’d lose patience. Keep yourself accountable and learn from everything you do. For me, when I screwed up the permalink structure on a WordPress site and didn’t have conversion tracking on a Thank You page, I vowed to never make those same mistakes again. Thankfully, I never had this problem and I continued to grow as a digital marketing professional in this space.

5. Understand Your Own Limits as an Entrepeneur

If you feel stressed or feeling physical pain in any way, listen to what your body is telling you and take breaks. It’s like point #1, but I’m talking more about your physical and mental limitations. If you know you’re way too in over your head, don’t take on the project or client. It’s okay to sometimes say no, even if the money on paper sounds good. You’ll be more successful once you understand the true scope of your value and communicate it to others.

6. Keep Your Ideas Written Down and Don’t Show Them Off

A true master never reveals all his cards in a poker tournament. Neither should you! Keep your secret weapons close to your chest. Be like Coca-Cola and their secret formula, having it locked away airtight! Or take a hint from Mr. Krabs here and be on guard all the time for any interlopers who might try to infringe upon your success. Any ideas you haven’t acted on, save them anyway. You never know when they’ll come in handy later!

7. Save Your Past Work in Multiple Hard Drives

Here’s another important thing I would have told my younger self to speed up becoming a good entrepreneur. From the very beginning, keep detailed records of what you did for these companies. You don’t know when any of them might go out of business one day. It always hurts to have to start over and develop social proof from scratch again, especially in a high-paced field like digital marketing or web design. You never know when these old writing samples, screenshots, Excel sheets, etc. might be useful once again for a LinkedIn portfolio of some sort.

8. Find Mentors You Can Learn From Quickly to Become a Better Entrepeneur

You will progress so much faster in your career if you have a few hard-working mentors who can show you the ropes in becoming a better entrepreneur. Whether it be learning the technical SEO principles or learning to set up larger-scale PPC campaigns, mentors are there to help you cut through the noise. You’ll be working with people with years of experience under their belt and will learn many techniques you will use for years to come. Don’t discount their experiences in any way or have an ego when they tell you what you can improve on. Learn and fail quickly, and then learn even more!

9. Have Gratitude for Everything You Do

Don’t forget to be thankful for the opportunities you have to succeed. Be sure every day to thank everyone who helped you to get to where you are now as an entrepreneur. Never forget your roots and always stay true to yourself. Don’t let money or riches corrupt your character. Ill-begotten monetary gains are not worth the paper they’re printed on. Do things in a way you can live with yourself. Use the money you earn to help others and to give back to your family and friends who love you most.

10. Become a More Empathetic Human Being

Ditch the “what’s in it for me” attitude. Don’t be a know-it-all entrepreneur, and let your results speak for themselves. This isn’t an ego-stroking contest. You are trying to help businesses and other people with their problems. Never lose sight of what’s important and again, do things for other people without asking for anything in return. Be your own George Bailey in your life and never lose sight of your character. Follow the Golden Rule and eventually, you will reap the benefits and have a whole wealth of knowledge and experience helping others.


Being an entrepreneur is about becoming the best version of yourself. It’s about letting go of your ego, finding the best people to work with, constantly learning from your past mistakes, and much more. I’ve learned many of these lessons the hard way and wrote this post so you can learn too. Thanks for reading my blog today and I hope you’ve enjoyed the content! I appreciate it.