Entrepreneurship: Biggest Business Regrets

As entrepreneurs and business owners, we’ve all had experiences or made decisions that we regret. But, we can definitely learn from those mistakes and regrets. In that spirit, the CarolRoth.com contributor network of business owners and entrepreneurs have been gracious enough to share their own personal business regrets, so that we can all learn from them. Their answers are presented below in no particular order.

You may notice some similar ideas listed, but I kept them separate, as something in the way one is framed may resonate differently with you.

1. Corporate World? Never Again!

I reinvented myself at 48 after being off-shored. This was the time to become the Warren I've always wanted to be. Now, at 51, I've worked hard and have become internationally published on food, cocktails and wine. My bosses all told me that I wasn't a very good executive assistant. But I didn't listen to them. Then, I finally got my chance to shine doing what I love! The rest is history. My take-away is to do what you love! NOW! Don't wait!

Thanks to: Warren Bobrow of Cocktail Whisperer.

2. Get Involved!

One regret I have as a small business owner is that in my earlier years and to some point even now, I did not get involved in my business and local community as much as I should have. Businesses often fail or succeed based upon their ability to effectively network and I know that I have not done this as creatively as I should. My business has not grown locally as much as I would like it to due to this.

Thanks to: Darrell Andrews of Darrell "Coach D" Andrews Ent.

3. Nobody Told Me...

...that my expertise alone would not be enough to allow my business to prosper! I began my solopreneur life as a scientist (a preclinical safety professional) with a business, not as a business person with scientific expertise. I’ve learned that unless you are working in a boom market, this is a recipe for anxiety and overwhelm, if not absolute failure. I wish that I had learned more about running a business before starting one!

Thanks to: Monique Y. Wells of Understanding Time Management.

4. Everyone's Friend!

The more and more I get into the deep dark, but exciting crazy life of being an entrepreneur (and having to pitch big clients daily), the more I understand the need to be everyone's friend. I regret not building my network of people years ago and becoming friends with everyone! I'm making up for it now. But seriously- be everywhere, be awesome, and be genuine.

Thanks to: Ryan Critchett of iMobileRescue iPad Insurance.

5. I'd Rather Have a Job!

My biggest regret was not partnering with someone at the beginning. I was under-capitalized and really didn't know how to be an entrepreneur! I've become entrepreneurial, but I'm not a natural. Some people, like my son, know what and how do to what they want. I had to learn! I wish I had had a mentor to show me the ropes of running a business, hiring, firing, and all of the "stuff" I need to do, plus my real work: creating commercials and web videos that sell.

Thanks to: Mark Alyn of Mark Alyn Communications, inc.

6. Get an Office

My biggest regret is thinking that I can literally work from anywhere...my bed and my couch were huge productivity/creativity crushers and it took me a while to realize that I was sabotaging myself & business. Once the decision to be a business owner has been made, create an office space; it doesn't have to be big (mines is 10 X 12). It makes a great difference in your productivity and creativity when you have a specific space to work. And make sure it's extremely comfortable to you.

Thanks to: Stephanie Coradin of Dembo Inc Administrative Support.

7. I Should Have Invested Early

My biggest personal regret was failing to invest in the publicly traded companies in the self storage industry early in my storage industry involvement. I knew my involvement would be a game changer, but I underestimated just how much the industry would grow over the years. I could have bought Public Storage PSA at $25 when I first came to work for StorageMart in 2000. Today, PSA is trading at $137. So, if you think you are going to make a difference, invest early in your industry.

Thanks to: Tron Jordheim of StorageMart Self Storage.

8. Shoulda' Started Sooner

Next April, I'll be celebrating 25 years in business as an executive coach, leadership consultant and speaker.

I have only one regret. I waited until I was 38 years old to start my business. I wish I had started sooner.

If you're considering starting a business, don't wait. The time and circumstances will never be perfect.

Thanks to: Bud Bilanich of The Common Sense Guy.

9. Shut the Door!

People on the sidelines will always have something to say about what you do. The 'shouldas' they offer are often not about you, but about what they 'woulda, coulda' done better (if you weren't in their way).

I wish that I had learned earlier in my career to trust my gut first before considering others opinions. I had confidence, but was afraid it would be perceived as conceit.

Always picture yourself as smart, powerful, and 'all that'- big enough to do what's right, no matter what anyone says.

Thanks to: Janine Darling of StashDaddy.

10. Timing is Key!

I started my business three years ago. I regret that I procrastinated for four years before I followed my passion. We delay what we need to do because we think that it is either too early or too late to start. Forget about too early or too late. Start now! Follow your dream! Tomorrow may never come. Timing is key!

Thanks to: Kamran Akbarzadeh of International Academy of Leadership.

11. Business Partners Gone Wrong

My biggest regret is not having my lawyer review my business partner agreement & dissolution. I dissolved the partnership incorrectly and she suddenly turned from a nice girl into a threatening, non-logical, wounded victim who wanted to take half my company. Always, always, have a lawyer review your contracts!

Thanks to: Kim Flynn of Kim Flynn Consulting: for Women.

12. Follow Your OWN Dream!

Way back 33 years ago, right during the start up of my own business, I decided it would be fun to join forces with a colleague who wanted to start a roller-skating rink. I always loved to skate, but that is NOT a reason to start a rink! I distracted myself from my own mission and it was a disaster from start to finish!

Get yourself straight about what YOUR niche and mission is, and go for that. Later, you can start a foundation to help fund other's dreams. FOLLOW YOUR OWN DREAM FIRST!

Thanks to: Sheila Van Houten of New Light Consulting Corporation.

13. Clueless and Kool-Aid Solution

When I transformed my practice from training to individual and organizational development, I drank the Kool-Aid specific to the great tools that I discovered. However, the best Kool-Aid needs to be drunk by others and I was clueless about this obvious fact. My regret is that I failed to invest one hour per day in expanding my own marketing knowledge. Now, everything begins and ends with creating engaging marketing actions so others will at least find my Kool-Aid, if not drink it.

Thanks to: Leanne Hoagland-Smith of ADVANCED SYSTEMS.

14. Regret? Never!

My biggest regret in business is that I should never have spent a nanosecond in regret.

It's vital to view the world as teeming with unending opportunities. To regret missing out on an opportunity is to suffer from myopia, focused on limitation. The only true restriction is generated in the mind. Opening it to unlimited possibilities squelches any feelings of regret.

When I was younger, I wasted precious time on regret. Now, I live from my best intentions without any regret.

Thanks to: Catherine Divingian of TIER 1 Performance Institute.

15. Connect Via Emotion- Not Info

We connect with each other through emotion, not information. When starting out, I spent too much time on the info & not on the emotion. In addition to learning about the client's biz, learn about the decision-making person, such as their hobbies, interests, family, etc. When first connecting with a prospect, I research them (e.g., school attended, social group involvements, etc.). Know the biz AND the person making the decisions! It is all about establishing rapport.

Thanks to: Edward Leigh, MA of Center for Healthcare Communication.

16. Researching Resources

We started this company in January 2008. Looking back, I am amazed that we survived the first couple of years. My biggest regret was not taking the time to find out what FREE government (well, our tax dollars pay for them) services were available to help jump start new ventures. There was capital and expertise that we could have tapped into that would have accelerated the process and made us profitable sooner. Take the time to research what is available; you will be pleasantly surprised!

Thanks to: Ben Baker of CMYK Solutions Inc.

17. No Loosey Goosey Contracts!

I wrote my own contract for an agreement with a ghostwriter. The client didn't like the writer's work and I had to agree with the client. The ghost had already been paid and wouldn't refund the payment. I had to eat $5K and pay another ghost to do the job correctly. It hurt worse than a bee sting!

Thanks to: Randy Peyser of Author One Stop, Inc.

18. We Worked for a Year on This!

A PR colleague and I planned a joint venture and we worked on it for a full year. As soon as we launched it, she told me that she was pregnant. The venture never got off the ground.

Thanks to: Jane Blume of Desert Sky Communications.

19. Give-A-Way

In my earlier days of business, I bartered away services that were more lucrative than what was being received in exchange. This taught me and the business a valuable lesson to be reasonable and fair within your own business first, so that you can assist others as you grow.

Thanks to: S. Capri Edwards of AGC Transport & Services LLC.

20. Not Realizing the Potential

I regret not realizing the potential that my business had to scale early on. I was too satisfied with breaking even and having a good time, without realizing that there was real money to be made if I got more organized and serious. I didn't go in with a business plan and I was only thinking short-term. That's the problem with starting a business with your hobby and not investing yourself into it completely. I'm getting my MBA now to arm myself with tools for a more successful future in entrepreneurship.

Thanks to: Pathik Bhatt of RAAHI Design & Apparel.

21. No Second First Impressions

When we began our company, we picked licenses that we thought would be good to brand with our product- ones that were more affordable and popular enough. Popular enough, however, is not good enough. As they say, you never get a second chance to make a first impression. We should have started out with spending the money on at least one or two really big name licenses, as in the end, it would have gotten us more exposure and sales. When introducing a brand, bottom line, come out as strong as possible!

Thanks to: Craig Wolfe of CelebriDucks.

22. Choose Your Mentor Wisely!

My ONE biggest regret as an entrepreneur was not choosing the right mentor when I started my business. A mentor should be someone that can add to your knowledge base and strategy - someone who amplifies your own skills and can see clearly where you need additional help. They must be honest and supportive, yet not sugar-coat the difficult messages that will surely help move you toward success.

Thanks to: Dianne Daniels of The DivaStyle Coach, Inc.

23. Started Sooner

I wish I started my business sooner. If I would have know then what I know now, I would have started much earlier in my life. Being an entrepreneur is the best thing that I've ever done and there are so many benefits and rewards to being your own boss. Not starting sooner is my one true regret.

Thanks to: Eula M. Young of Griot's Roll Film Production.

24. Regrets are a Personal Killer

One of my biggest regrets is not taking advantage of many of the free/low cost business classes that are either offered locally or online/teleconference. I spent much time "reinventing the wheel." As a way to stop myself from feeling regretful ongoing, I lead a group of individuals with many years of experience that have been downsized and are looking for options for starting a business or increasing a part-time business they have. I share what I have learned, so others do not make the same mistake.

Thanks to: Carol Coots of Practical Cost Reduction.

25. You're Not Perfect!

While there are many things that I wish I'd done differently, I'd have to say my biggest regret is having the attitude of perfectionism. Nobody gets it perfect right out of the box. It's too easy to say "Let me tweak this or that before I launch". If you keep tweaking, you'll never get anything launched. Before you know it, you've acquired a fear and have no business because you can't get anything put out for public consumption. Just get it out there and tweak it later. You'll be happy you did!

Thanks to: Becky Fisher of Magical Media Solutions.

26. Play Big and Burn the Boat!

My biggest regret is simply that I waited so long to play big. I held on to my 'bread and butter' monthly contract as a freelancer and consequently, was unable to give 1000% to my new biz.

But life has a way of intervening and our big contract came to an organic end after 7 years.

Since that time, only a month ago, I have made HUGE strides in my business in every way imaginable. I wish that I had made the commitment to burn the boat sooner. Wow!!

More energy put in = more success!

Thanks to: Share Ross of Video Rockstar University.

27. My Biggest Business Regret!

My regret is letting my employees know that I was the owner. I have many strengths, but managing employees is not one of them - I am too nice. I have learned to pretend that I am only "the manager", not the "mean boss." Now, my employees happily follow my rules because now, they see me as one of them. If they don't follow the "owner's rules", I tell them I will get fired. I get to be good cop and bad cop all at the same time, but everyone still likes me. It works great!

Thanks to: Aimee Elizabeth of Become a Self-Made Millionaire.

28. Better Late Than Never

The biggest regret that I have in my online business is - I wish I would've known then what I know now! SO much useless time could have been saved!

To those just starting out, here's a few things that I learned:
1. Even baby steps will get you there if you keep moving forward.
2. If it is not working for you - stop it & try something else!
3. Find the thing that you love to do & tie it to your daily business.
4. It's ok to ask for help when you need it.

Oh yeah... RELAX!

Thanks to: Barb Roehler of BR Innovations LLC.

29. Going Corporate

I started as an entrepreneur when I was 14 and was doing well, but at around 21, somehow, I got convinced that a MBA & high paying corporate job was the right career. I wasted 2004-09 on multiple corporate roles at Fortune 50 companies only to realize I did NOT want it. So, my biggest regret is the lost years that I could have spent building an awesome business. I learned many skills, developed a strong network, & made good money while doing the time at 9-5 jail, so no hard feelings.

Thanks to: Devesh Dwivedi of Breaking The 9 To 5 Jail.

30. Learning from Mistakes

Ugg! I feel like I have too many to mention! But when I was running my first company, the skateboard brand Saturday Skateboards, I can honestly say that we were spending far "bigger" than the company was. We went to tradeshows, ran full-page ads and overall, just spent more than we should have. We really would have been better served skipping the tradeshows - not enough "hypodermic" sales. Those funds would have been far better allocated as a bonus to a salesperson or more organic sales efforts.

Thanks to: David Collier of Ink Floyd, inc.

31. Well, Shut My Mouth!

I so regret not taking advantage of a warm lead that I received a year ago- a potential email intro to a powerhouse decision maker at American Greetings (the card company.) A friend had met this bigwig at a trade show in Vegas and had gotten her insider email and shared it with me. I never followed up. To this day, I don't know why, but right now, I'm going to send that email prompted by this invitation to share my regret KNOWING that this is a Universal prod to own my power. Thanks Carol!

Thanks to: Ellen Whitehurst of ellenwhitehurst.com.

32. Pay Yourself First

While every entrepreneur I know has gone without a paycheck occasionally, my regret is not paying myself what I'm worth during those early years. Instead, I chose to reinvest in the business. I now believe that I would have adjusted my business model more quickly had I not been willing to "bootstrap" the business. Lesson learned!

Thanks to: Elene Cafasso of Enerpace, Inc. Executive Coaching.

33. Should've Made Values Public

It was only in 2002 that I started being very public about my commitment to ethics and green principles. The commitment was there all along, and when I embraced it very publicly, my business took a quantum leap.

Thanks to: Shel Horowitz of Green And Profitable.

34. It was Retail!!!!

A retail business was the last thing that I ever wanted. The public is not easy to deal with.

With access to a new fleet of vehicles every year, I opened a car rental bus. It seemed easy. Rent the vehicle and off goes the renter.

I could not have been more wrong. It's the most retail of all retail businesses.

You live with the vehicle and the renter from the time that they pick it up until the time that they return it.

I lived with this regret for 7 years until it was successful enough to sell.

Thanks to: Harris Glasser of Serving The People Press.

35. Techie Love

The man who is the co-creator of my website, owner of its web-hosting company, and my technical administrator, is now my ex-boyfriend; I regret his input and participation. He has mismanaged my personal trust, yet his energy is interwoven permanently into my dreams and vision. I do believe that my site still contains residuals of his energy; a concrete example is that on the day that I conducted a cord cutting ceremony to personally heal from this break up, the server to my site went down.

Thanks to: Joy Holland of Facets of Joy.

36. Let Mentors Mentor!

Early on, three successful people, whom I did not know well, went to bat for me, made phone calls, asked good questions, and offered advice. I didn’t realize the importance of these gifts, nor did I maintain relationships with the individuals. I realize now that they were mentors and I could have benefited from these associations. I try not to repeat the process when I advise people just starting out.

Thanks to: Flo Selfman of Words à la Mode.

37. Why Wait?

Like many entrepreneurs, I always knew that I wanted to own a business. I also knew it was risky. So, I waited. I needed more experience, a better business plan, and more financing. The truth is that sometimes, you just have to make the leap. Two years prior to starting the business, I was bored with my job and disillusioned with corporate politics. Would those years have made a huge difference to the success of the business? Maybe not. But, I would have been happier and that counts for a lot.

Thanks to: Cynthia Kay of Cynthia Kay and Company.

38. Wandering Minds

One of my biggest regrets on my journey of entrepreneurship was selling too early. I was so eager to get my business out there & build my network that I began pitching too early. The problem with that strategy was that my business model was UNCLEAR,& I did not understand what service I wanted to bring to the marketplace. When I would network, I would always pitch a different service; This lead to the networks lacking confidence in my ability to deliver.
Case in Point: Get CLEAR & Get FOCUSED.

Thanks to: Justina Ajusma of JSC Management.

39. Not Following My Own Protocol

We all have some sort of format or rules that we follow as we get a sale for service and follow up on client. My biggest regret every time that I do it is trying to please a client by making it easy on them and breaking my own protocol. Saving time, not getting their feedback, or doing a step for them, not matter how much they "trust" me or I think that I understand what they want- it always, always, comes back to bite me.

Thanks to: Gwen Hawver of Vision Interface.

40. Little Faith

My biggest regret as an entrepreneur is that I did not have faith to start sooner. I have struggled with self-esteem issues and that has delayed my progress. I am a successful real estate owner and have just formed a company teaching people how to manage their money without
deprivation. However, I sometimes wonder how much more I could've achieved had I just believed. I encourage everyone to never believe the naysayers and hype.

Thanks to: Timmie The Teacher of NewFitWorldTV.com.

41. Fitting the Closest!

Indeed, you are always thinking of the best people for your most-cared startup company for a feel good operation. And with an intention to help the favorite among your social network - family and friends, you are going to make them fit, not thinking of your vision - are they the right ones? That is my biggest business regret! The BIG DEAL - win the argument and lose the person OR lose the argument and still win the person? The rest of the story is the BIG IMPACT to your image. Be blessed!

Thanks to: Jennifer Pacatang of Forefront Solutions Builder Intl Co.

42. The Truth About Passive Income

Passive income is great, but it takes a lot longer for most people to create it than active income. So, you tend to focus on the active income when you are starting out. But, if you don't start building passive income too, you never get out of the job you've created for yourself. The challenge for most people is not creating the products, but the copy and driving traffic to it. Knowing what I know now, I would have studied how to build passive funnels and drive traffic to them a lot sooner!

Thanks to: Ellen Violette of The eBook Coach.

43. I Won't Do That Again!

We always have regrets, don't we? My biggest regrets are definitely about not doing my due diligence. I trust referrals and just take them at face value - I've learned that I have to do my homework, because lots of referrals (especially now with social media) are not as solid as we hope. Blindly trusting can be a costly lesson. Now, I do my homework no matter what it is I'm considering, in terms of adding to my business growth or service.

Thanks to: Kellie Auld of Simply Communicating.

44. Investment Loss

I once told a special friend and mentor, who was looking for a real estate investment, about an opportunity to invest in a property already in the process of being sold. It was a timing issue that looked like an opportunity to help both a motivated buyer and seller. I felt like this was just the opportunity that my friend was looking for, but the buyer walked at closing and my investor lost her money. I had no regrets in business until this situation and won't have peace until I fix it.

Thanks to: Shelia Samuels.

Do you have a business regret that wasn’t included? If you do, please share it below. And as always, many thanks to everyone that contributed to this article!

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