Top 10 Challenges Facing the Successful Entrepreneur or What Keeps You Awake at Night?

1. Awareness – What do you know?

  • Do you know where you’re going and how you’re going to get there?
  • Do you know what you’re good at – and what you’re not?
  • Do you need to know how to do everything in your organization?

2. Needs, Resources, & Roles – What about the hats?

  • Can you wear all the hats – fill all roles?
  • Will you recognize when it’s necessary to stop wearing all the hats?

3. Time Management – Where did the day go?

  • Have you become a “fireman,” putting out fires most of the day?
  • Are you focused on details at the expense of a bigger-picture perspective?
  • Do you hear yourself saying “Why can’t there be more hours in the day?”

4. Sole Responsibility – But being the leader has perks, doesn’t it?

  • Such as – The buck always stops here?
  • And – Are you ever “off” work or “on” vacation?

5. Focus & Vision – Can you see clearly now?

  • Do you have a laser-like focus?
  • Is your vision too far ahead of your organization’s position?

6. Managing Growth – Will it grow on its own?

  • How will you scale the organization and get it to the next level?
  • Do you set aside time for association development, no matter how busy you are with existing work?
  • When is the right time to add an employee, manager or management team?

7. Employees – Do I have to be good at HR, too?

  • Are you able to hire the right employees and managers?
  • Do you know how to provide effective feedback?
  • Does loyalty to friends who are employees cloud your vision?

8. Delegation – So you hired the right people, isn’t that enough?

  • Can you delegate … or do you say “I can do it quicker and better myself, or I don’t have time to delegate!”?
  • Can you tolerate mistakes or different approaches?

9. Feedback – Where’s mine?

  • Is there anyone who will engage you in passionate debate about a business idea?
  • Where do you get objective feedback?

10. Giving Credit – Does your ego get in the way?

  • Is it enough to be good at what YOU do?
  • Can you give credit where credit’s due?

Can you answer these questions?

Michael Shapiro – Dynamic Management Solutions

One Response to “Top 10 Challenges Facing the Successful Entrepreneur or What Keeps You Awake at Night?”
  1. smallbizexperts says:


    As a fellow small business owner I found these questions awesome! It is exciting and terrifying running a small business. Just having your questions listed provides an excellent source of focus and grounding, if that makes sense 🙂 Thanks for providing a simple to follow sanity check list.


    Chris Nastav
    Owner, KC Web Specialists.

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