Business Development · Entrepreneurship

Is it normal to feel like you are sabotaging yourself in business?


January 27th, 2020


I am new to cofounderslab, so please excuse me if I come off as naive in posting this question here.

First of all, let me lay a little context for the question... Some people are obviously unfit for the stresses, responsibilities, and liabilities of entrepreneurship. They choose to spend their time watching GOT reruns, spend frivolously, and enjoy a more consumerist lifestyle than most productive people can afford.

However, what if you spend all your time reading, exercising, working on your small business projects, trying your best to apply all the lessons you learn, sacrifice consumerist activities that you used to enjoy, yet you still can't seem to reach your goals?

I feel that I may be missing something because I'm uneducated compared to many of the members here. I was homeless and out of school at age 16. Got my GED, but no college degree. Didn't get those "normal" formative years of finishing high school or college and still experience the effects of something like PTSD from my years on the streets (I am 39).

I've done what I could to educate myself: Great Courses, Certificate programs from Cornell, Duke, etc. I got jobs in video production, web development, then project management... But despite knowing others that were making lots of money in these fields, I barely ever made enough to get by. Most of my jobs were freelance and when I was able to get a position in a company, it was rarely a coveted slot. Most of the companies were fly-by-night.

A relative died and left just enough money for me to get in trouble with. I was very blessed and am thankful to have received the opportunity. I bought a short sale house to live in, paid for. Then used the rest to put a down-payment on an existing Bar in Downtown Atlanta (2017). In my zeal to purchase a business, I pretty much made a bad purchase. I can't really blame the sellers.

Though the bar is in much better shape now, I had to go through the gruelling process of raising revenues 100k year-over-year *just* to make a small profit. I still have to work on this business around the clock and the effort is simply not compensatory with the amount of time and effort.

I don't know if I suffer from "Poor Dad" syndrome or what. I am not in any way trying to mope or create the illusion that the cards are stacked against me. I want to find what I am doing wrong. My biggest concern is that I am subconsciously sabotaging myself. I see myself as "poor". I try not to allow myself to do that, but I've literally been broke since I've owned the bar (I didn't even have debt over $2k before owning the bar, now I'm in for about $20k left on the bar, $20k in debt accumulated just to cover the slower parts of the season and year 1). Combine that with growing up poor + a 2-year homeless stint in New Orleans and it's been tough for me to see myself as affluent or successful. I try to have a positive mindset and to follow the instruction of business people, but after the better part of a decade of intense effort and self-education, I've gotten my ass kicked.

Though I logically don't believe it, I *feel as if* I am some kind of repellant for profitable ventures. I should at least be able to make a "comfortable living" if I am adequate at entrepreneurship, right?

Anyone else just keep hitting roadblocks and making mistakes with their investments (both time and money)? I want to do the right things, I want to be productive and provide value to people, I want to be a team player, but I don't feel like I'm making the progress that I wish I could make.

Paul Garcia marketing exec & business advisor

January 29th, 2020

Having run the trade association for bar owners, I am exceptionally familiar with your scenario. And while you've probably already kicked yourself for what may have turned out to be a bad choice in buying a bar, a bar is just like any other business. It requires the same 6 fundamental business skills as any other. And no owner ever masters more than 2. You will always need support for your business to thrive, whether that's employees, consultants, or advisors.

A bar has a few quirks because it's a regulated business, but like I said, it's just another business. Too often people go into owning a bar wide-eyed and excited because they want the lifestyle they imagine to be attached to it. That's an illusion and an almost sure path to hardship.

My guess is that you are working hard, but you probably lack the kind of support you actually need, making everything harder. Frankly $40K isn't a lot of debt for a bar. Many people are in for hundreds of thousands. But depending on your size and overhead, it can be a scary number no matter what the amount.

Here are the six fundamental skills I want you to think about: marketing, sales, organization, efficiency, people, and leadership. They aren't the only skills, but they're the fundamental ones. Which one or two are yours? Then I want you to think about who is filling in the skill gaps you lack. Yes, you might touch them all, but you're not the expert in more than two. No one is.

Do not, and I repeat it, do not treat your employees like family. You run a business, you're in business to make money, and if you don't make money, all the people you care about at work are out of a job and so are you. You can like, respect, and be friendly with your employees, but first you have to train them properly, hold them to a high standard, and support them properly (meaning set them up for success).

I could give you a lot more specific advice if I was still doing that kind of consulting work. And I would be willing to read email and give you some initial guidance if you want to get into specifics off this forum.

The only thing that sabotages your business is not taking the steps to get the support you need. Yes, I know everything takes money. But the longer you wait to get it under control, the harder it is to spend what money is left.

Every bar owner could fix their struggling business if they applied themselves, owned their mistakes, and made changes to adopt best practices. I'm a nice Jon Taffer, I don't yell. But I also don't sugar coat the situation when something needs adjustment. There are always nuances because every bar and market is different, but that's not what most people need to worry about. Most people fall down on the fundamentals, and that's trainable.

Doug Slattery Founder of AECS Consulting Inc. Developing apps for IoT smart home & office.

January 27th, 2020

I think you will find as you meet more entrepreneurs is that you are not alone. It took me a while to realize that myself the more people, uhm, I mean entrepreneurs I talked to personally.

If you are passionate about what you are doing, do it for all it's worth and never give up.

I don't have a college degree either, but have a knack for what I'm doing - technology.

I used to feel insecure about that, mostly about getting employment until someone once told me "You don't need a piece of paper to prove how smart you are." When I heard that I realized the sky is the limit and took off to a really successful career.

I left the work force mid-2018 to pursue my startup full time & don't regret the decision even with the anxiety, uncertainty and everything else that goes with being an entrepreneur. The alternative is the depression & dreading Sunday evening of having to go back to the job on Monday morning.


- Doug

"Nothing is impossible if ImPossible"

Lisa Cutter Marketing Maven

January 31st, 2020

I wish this wasn't posted anonymously, as I'm in metro Atlanta and would love to connect with you. Hope you've had a chance to read the other great responses here. In the meantime, looking forward to getting a connection request from you on LinkedIn. :)

gkraeger Looking for a partner that can setup a sales team and/or partnerships.

January 27th, 2020

Don't give up don't ever give up. I was homeless for a short time, it happens, but it didn't stop me and it didn't stop you. You have already overcome so much. I'd like to talk to you offline depending on the bar you own I might be able to help you drive revenue.

EJ Steele Business and Executive Coach at Task At Hand Consulting, LLC

January 28th, 2020

What you are experiencing comes along with the territory of entrepreneurship. In fact, "hitting roadblocks and making mistakes" is part of the ride. Without those moments, you'd have little or nothing to reach for. One item that comes to mind; I remind clients to remain mindful and intentional about the words and language, etc. that you use (to describe) [read: against yourself]. The way that you speak of (and subsequently treat) yourself has a greater impact than any outside influence ever will. Suggestion: Take another (read: closer) look at how you describe your progress to date - and consider what it might look like if you viewed your journey through another lens - one that illuminates/acknowledges the obstacles you overcame and progress made (versus the "downside"). It sounds to me as if you have come quite a ways - keep going and pushing yourself. The toughest parts are the self-examination and evaluation - and that's what will get you to where you want to be. Reach out if you'd like to speak further.

June Jewell

January 28th, 2020

Hi - I feel your pain. I have been an entrepreneur and CEO for 30 years and even sold a business but still suffer from self doubt, frustration and thoughts about quitting. I agree with the others that the most important thing is changing your mindset. What has been helpful for me is listening to Abraham-Hicks on Youtube. I believe it has helped me and has helped many others to find success by changing your thoughts.

Another thing that comes to mind is how to grow revenue in your bar. Sit down and ask your bartenders and servers how the bar can be better and serve customer better. Collect the contact info for every customer that comes in and offer them discounts for coming back (free appetizer with drink, etc.) and incentivize them to bring their friends. Ask them what they like and don't like about coming there and make changes they recommend. I am shocked at how many restaurants and bars don't do these simple things to grow business and especially regulars. There are many things I don't know about your business such as location, but there probably are ways to make it better.

Good luck and believe in yourself. You can do anything!

epueme emmanuel Tech Serial Entrepreneur/ Start-up Strategist and Analyst/ Business Analyst

January 28th, 2020

My friend, currently I am in a similar situation but something brought hope to me.

It was a sentence I heard it says "God always places your next big step within your present step, within your reach".

Meditating on this I found out that what I need to breakthrough is within my capacity and reach in fact within my environment in my mind, I just need to discover it.

And suddenly I found a breakthrough idea.

So you can sustain this mindset.


Ilana Hakim Cofounder, CXO

January 28th, 2020

Hi, My suggestions to you are 1. Hire a business mentor that will help you sort everything out 2. Work on your beliefs that your are unable to succeed or bad in business. It’s a self fulfilling Prophecy... I understand where you are coming from because I myself think of my self as bad in business but I also don’t really feel like it interests me. I focus on doing the things I like and am passionate about... Good luck in your path, and believe in yourself (which also means asking for more money because you deserve it), because if you don’t believe in yourself , why should anyone else? נשלח מה-iPhone שלי