The 13 Most Common Entrepreneurial Pitfalls: Source, Symptoms and Remedies

It seems that everyone on Instagram is an Entrepreneur or CEO. What used to be a high risk and scary choice, has now been glamorized into fast money, luxurious lifestyles, and ready-set-go businesses.

A picture is worth a thousand words, but the stories behind the glossy pictures are anything but fancy. I know the true stories of self-doubt, self-sabotage, and business burnout.

Over the years I’ve seen the same 13 challenges and entrepreneurial pitfalls in myself, my clients, and other entrepreneurs:

  1. Not Having a Clear Focus/Mission
  2. Trying to Be All Things to All People
  3. Lack of Revenue Diversity — Relying on One Client
  4. Imposter Syndrome
  5. DIYitis
  6. Isolation
  7. Burning the Candle at Both Ends/Lack of Self-care
  8. Taking it Personal and Not Making it About the Client/Customer
  9. Not Going All In/ Not Showing Up at 100%
  10. Not Charging the Appropriate Amount (usually too little)
  11. Investing in Tactics and Not Youself or Business
  12. Not Taking/Accepting Help
  13. Expecting Success to Come Easy with Minimal Effort

But how do we overcome these challenges and entrepreneurial pitfalls?

We start a new conversation.
We get honest
We get real and we get to the root of the issue.
Simple right? Now go do it!

It would be unfair to leave you with a list and a simple three-sentence plan.

In the next section, we’re going to dive into the source, symptoms, and remedy for each pitfall. Before we get going, I suggest writing down, the numbers of your pitfalls. Don’t be afraid… I deal with and have dealt with all 13!

1. Not Having a Clear Focus/Mission

Source: Information overload. The entrepreneur starts with an initial excitement and idea to follow and then, like Pac Man, starts gobbling up all the ideas. With a lack of organization and filtration device, the ideas get muddied. What once started as vibrant colors and ideas have now mixed into a glob of muck.

Symptoms: Squirrely focus. Distracted easily. Persuaded easily by others. Overwhelmed. Frustrated. Frazzled. “Yes” to all the things.

Remedy: Stop. It’s time to go back to square one before the business was ever in motion. What was the core idea or inspiration? What about it excited and motivated you? This is where your new mission and focus will be developed. If you are still unclear, reach out to trusted advisors or a business coach for clarity. This will be uncomfortable at the start but stick with it until you feel a focused energy.

2. Trying to Be All Things to All People

Source: People pleasing tendencies. Not wanting to disappoint people by saying no. Desire to be “The Nice Girl or Guy.” Seeking of Likeability.

Symptoms: Burnout. Overloaded schedule. Triple bookings.  Feeling of being taken advantage of. Plays roles that don’t suit skillset. Feeling of being helpful, but helpless. May suffer from reoccurring colds or illness.

Remedy: The Triple D Method to Time Management. All decisions will be based on the following three criteria:

  • Doability: Can it be done with the current resources (time, skill, and manpower) as requested? If no, see “Delegatability.” If yes, see “Desirability.”
  • Desirability: Does this feel like a treat or punishment? If it’s a treat, get it done! If it’s a punishment, see “Delegability” or use the power of “No.”
  • Delegatability: Can this task realistically be performed by someone other than you?  If yes, delegate away. If no, and it failed the “Desirability” and “Doability,” that’s a “Triple D Fail.”

You are only to say yes if it’s a “Triple D Success.”

3. Lack of Revenue Diversity — Relying on One Client

Source: Security. High Levels of Trust. Single Focus.

Symptoms: Scarcity mentality. Anxiety around outside factor. Worry around when the well will dry up. All or nothing mentality. Increased stress. Lack of sleep. Weight gain/Weight loss related to stress.

Remedy: Business Development. Who are the next 3-5 organizations/clients that would benefit from your services? It’s time to pick up the phone or write some emails. If a client is responsible for more than 40% of your revenue, it’s time to diversify. It’s easier to make up 40% than 100%.

4. Imposter Syndrome

Source: Lack of confidence. Self-doubt. Limiting beliefs around being qualified/verified. Past examples of failure, being unsure, witnessing failure in others.

Symptoms: Self-sabotage. Not showing up as an expert or thought leader. Playing small. Selling self-short.

Remedy: Create Your Credentials. Just like in school you had to pass a core curriculum, now is your chance. Write down a list of the credentials you need to be a qualified entrepreneur. Seriously. Don’t make it about anyone else. What do you need to learn, experience, gain expertise in, connect to? Create a 101, 201, 301 and 401 syllabi and go from there. After you’ve accomplished your course load, you get to graduate! Yes, you need a ceremony, cap, gown, and diploma!

5. DIYitis

Source: Lack of trust. Past disappointment. My-way-is-the-only-way mindset.

Symptoms: Overwhelm. Overload. Burnout. Distrust. Micromanaging others. Taking back control after delegating. Not outsourcing when appropriate. Slowing down progress. Project stall out.

Remedy: Recruit a Trusted Partner. Whether it’s a colleague or coach, you need someone who has your back and will give you honest feedback and input. You can’t do it all and you shouldn’t have to. What do you need support with? What can you easily move off your plate? Start small and work to build trust with others. If you assume everyone will burn you, you’re probably attracting in people who will. What if you could set your sites on someone who will be truthful and direct with you? Even if you don’t like what they have to say, at least you know where they stand. And how awesome would it be to move things off your plate and focus on your strengths?!

6. Isolation

Source: Fear of rejection. Desire to focus inwards. Introversion.

Symptoms: Refuses social invitations. Lack of networking and connection with others. (See DIYitis). Rejection of idea sharing and brainstorming.

Remedy: Exposure. Sign up for a Meet-Up group or networking event. Call a friend or two. Meet a colleague or client for coffee. Get a shower, get dressed and get out there. Your home office funk is seeping into your pores, it’s time to fresh up your body, mind, and brain!

7. Burning the Candle at Both Ends and Lack of Self-care

Source: Assumption of Machine-Like Abilities. False Sense of Unlimited Energy.

Symptoms: At its most extreme level, illness and burnout. Initially, it is shown as an unstoppable force. Others envy their unstoppable abilities that seem like the Energizer Bunny. For outsiders, they keep going and going without sleep. Without necessary care and recharge, they undoubtedly crash.

Remedy: Sleep (7 hours+), Meditation (5-10 minutes per day), Walking outdoors, Yoga, Nutritious food. If you’re familiar with Maslow’s hierarchy of needs, these are at the foundation. If you want to run efficiently like a machine, you’ve gotta keep it fueled and serviced.

8. Taking it Personal and Not Making it About the Client

Source: Fear of being wrong. Fear of failure. Scarcity mentality. Over-personification with business.

Symptoms: By only focusing on one opinion, the entrepreneur is either all right or all wrong. There is no gray area. With a personal single focus, decisions are made on emotional impulse and reaction. Feelings of disconnection and rejection. Internalization of rejection. Judgment. Energy sinks with each rejection.

Remedy: Objectification. You are not the business and the business is not you. Your business is your product/service for clients/customers. By focusing on the needs of those purchasing your goods and services, you can make comprehensive, data-driven and objective decisions. Each failure and success may be a result of your decision, but it does not define who you are.

9. Not Going All In or Not Showing Up at 100%

Source: (See Imposter Syndrome) Lack of confidence. Fear of failure. Fear of success.

Symptoms: Hesitation. Underselling expertise. Lack of risk taking. Unconfident body language. Fidgeting and lack of focus in conversation.

Remedy: (See Imposter Syndrome Remedies) Get to Your Why. It goes back to your why? Why are you an entrepreneur? Why are you taking some safe risks, but not the necessary ones to grow? What are you really afraid of?

10. Not Charging the Appropriate Amount

Source: Fear of rejection. Getting into Client’s Story. Assumption of Value. Interpretation of Lower Value. Lack of Confidence.

Symptoms: Stating prices and then quoting lower. Assuming client doesn’t want to or can’t pay prices. Afraid of people saying no. Consistently take money off of the table before the negotiation has begun. Acknowledges they could be making more, but find it hard to ask.

Remedy: Set Your Prices, Value, and Rationale. This is where you let the facts run the show. Do your research, how much are your competitors charging and what is an appropriate rate? What value do you bring to the table (see your credibility exercise in Imposter Syndrome)? Now write down your rationale for each price. This is your new internal and external script. Until you know it by heart and believe it, you depend on it.

11. Investing in Tactics and Not Yourself or Business

Source: Belief in the Magical Pill. Immediate Gratification. Avoidance of Discomfort. Lack of Focus or a Plan.

Symptoms: Multiple purchases of “Get Rich Quick” or “Learn this Tactic” program, but fails to full implement or see results. Thousands of dollars have been spent, but not invested. Uses language like “If only I…” or “When this gets done, then I’ll be successful.” Frustration at lack of results. Blames others for lack of success.

Remedy: The Mirror. What is it that you’re avoiding that you’ve been needing to do in your business? What are you not taking care of within yourself or relationships? The issues we see in our business are a direct reflection of what we’re not managing internally. Take a deep hard look in the mirror and start asking for help.

12. Not Taking or Accepting Help

Source: (See DIYitis) Lack of trust. Fear of burdening others. Fear of disappointing others.

Symptoms: Overwhelmed. Low energy. Dejected. Feeling like a failure.

Remedy: Stock Your Shelves. Just like in a supermarket, you’re going to do an inventory check. What are you feeling low or out of supply in? Motivation, support, a hug? Note what you need and then look at your supplies. Who around you can support you in restocking your shelves? Reach out and ask for exactly what you need. I guarantee you’ve got a long line of people ready to help you!

13. Expecting Success to Come Easy with Minimal Effort

Source: Instagram-Insta-Success Stories. Comparison. Instant Gratification.

Symptoms: Lack of patience. Frustration at delays. Anger. Dejectedness. Impulsive decision making. Quick-fix program purchases.        

Remedy: Build Your Blueprint. What does success look like for you? How long will it really take to get there? What resources do you need to support it? What daily, weekly, monthly tasks do you need to support it? What’s your contingency plan if it doesn’t work out?

The Key to Successfully Overcoming Entrepreneurial Pitfalls

The key is to think on a longer timeline. You may have daily wins and challenges, but your business will hopefully have a longer shelf-life than 2 weeks. Patience is the key.

If you have overnight success, the bar gets set even higher next time and the chances of disappointment are even greater. Start smaller and build from there. Consistency, patience, and follow through are your best friends.

It’s not sexy, but neither is losing everything and living on your mom’s couch.