Success Roadblocks in Business – Insights from 6 Entrepreneurs

Success roadblocks faced by Entrepreneurs
Smart Entrepreneurs know that making a business thrive is not a joyride. It’s filled with bottlenecks, changing trends and facing personal roadblocks.

Business success is about embracing new challenges and tackling all that’s challenging you.

Having to do-it-all seems to be a common imperative of running your own show. From business development to bookkeeping, design to data gathering, excelling at everything can be quite a task.

Smart Entrepreneurs know that making a business thrive is not a joyride. It’s filled with bottlenecks, changing trends and facing personal roadblocks.

Most say they’re always learning. And re-learning. Sometimes even ‘unlearning’.

Read candid insights from 6 Entrepreneurs about challenges – what functional or soft aspects of business they find tough, and the takeaways for the all of us.

Insights on Success Roadblocks in Business


Not all Skills are created equal  

The marketing is the hardest for me because I’m not strong
in it and really don’t understand it as well as I should to get attention for my business.

Earline Marshall, President & CEO, Marshall Management Group


I always find book-keeping to be a challenge.  I love the creative side of my business,  I am more challenged to sit down with numbers!

Laurie Tieman, Owner, Arrt Promotions


 Bottomline: Recognize the Pain Points 

Also Read 20 Soft Skills for Your Road to Success

There’s a will, but maybe not enough way

 I am better utilized in the areas that make money.  My biggest challenge at the beginning is being a one woman show. It requires a lot of time and personally meeting with other people to explain the idea since it’s never been done before. The face-to-face marketing is exhausting. I am currently looking for help so we can expand.  

 Camille Miller, Founder & Executive Director, The Natural Life Business Partnership


I’m so passionate about what we do, and what our ultimate goal is, that inevitably, where there’s a will, there’s a way. I’m not very adept at social media, but for the same reason, I’ve outsourced that to another Salary Coaching teammate.

Olivia Jaras, Founder, Salary Coaching for Women


Time management and finding the right assistant.

Dr. Syleecia ThompsonDYG Management Group


 Bottomline: Seek collaboration when you need to 

Also Read 7 Winning Tactics to Do Less and Achieve More

Can do it doesn’t mean we have to like it 

I personally hate the finance part so I farm that out to a skilled professional. Task outsourcing Checklist for Entrepreneurs I really don’t like bookkeeping. Can understand it but it’s frustrating for me so I prefer not to take my time there.  I had a summer intern help with data entry too but I was doing it before that. It was a great way to learn.

I believe it’s important to do the job yourself before handing off a piece of your business for someone else to do, so you understand the challenges it brings.

Camille Miller,  The Natural Life Business Partnership


Accounting. I hate it.

Dr. Syleecia ThompsonDYG Management Group


 Bottomline: Leverage Strengths. Outsource the Rest 


Deal making Challenges


Once I get the client I am excited and enjoy the process of working with them and getting things done.  It’s making the pitch and closing the deal that I find most challenging.

Earline Marshall, President & CEO, Marshall Management Group


Sales is always the most challenging part of our business.  Acquiring new customers, diversifying into new verticals and staying ahead of the competitor are all key to staying viable and growing.

If we are not growing, we are going out of business.

Sandi Webster, Principal, C2G Partners


 Bottomline: Focus on the Success Lever 


Also Read 8 Tips to Perfect your Business Pitch

Regulatory Factors


Attracting new clients, especially because this service is not covered by insurance.

Nidhi Idnani, Owner, iReikiNow


I would say bookkeeping gets tricky because of doing business in other countries.

Olivia Jaras, Founder, Salary Coaching for Women



 Bottomline: You don’t (or can’t) Control it all 


Everyday brings a new Challenge


Most of our contracts are on a statement of work, attached to a purchase order, so payment terms and timing are already defined.  However, managing my day-to-day is challenging.  There is always a “fire drill” that happens where we have to go off course to take care of it, and getting back on track can be difficult.

Sandi Webster, Principal, C2G Partners



 Bottomline: Streamline and prioritize when things go off-track 



Self Assessment – Do you have a clear picture?

Skill Mapping is a great way to evaluate your own abilities to find out what you do best and what you instinctively avoid or prefer to stay away from. Print and fill out the worksheet below to assess your skills & strengths.

Do this Skill assessment exercise

Why not focus on what you do best!

The above exercise on Skill Mapping is a fun but spot-on way of prioritizing your work aligned with your skills.

Even if you run a tight ship and would rather not spend on hiring help right now, why not consider collaborating or bartering services. Many online platforms like Maroon Oak offer avenues to connect with other entrepreneurs who want to do the same (link).

Also Read 14 Great Ways Entrepreneurs Collaborate to Win

Add to your repertoire! We all are a work in progress 

The best leaders know at least a little of everything in their business. And you’re the captain of your ship.

Want to get comfortable with social media? Overcome the fear of public speaking? Learn a CRM system? Why not opt for learning in bite-sized pieces that’s fast and focused  towards your goal. If you need motivation, or have a friend who’s smart at a skill, make learning fun with a Girls Night Out learning.

10 Awesome reasons to join Maroon Oak

The Small Stuff Counts!

“I actually don’t mind doing the little things,” says Camille miller. “It keeps me grounded in what it takes to be a business owner.  My life is very balanced so I know when to shut off and  make time for myself and my family. Time management is a challenge for most business owners but I seem to handle it well.”

Your skills will differentiate you from the pack, but acknowledging the weak areas and finding ways to combat them will truly open up your success path.

Go ahead – Skill Up or Skill Out. You can’t lose.

Pooja Krishna

Pooja Krishna is an Entrepreneur, Consultant and Mom. She has worked both in large corporates and managed startups over the last 20+ years. A co-founder of Maroon Oak, she’s also founded Win Thinks, a small business consulting company, and Trading Paces, which educates amateur and pro stock traders. 

A trivia buff and yoga & hula hoop enthusiast, Pooja loves spending time with her family playing board games and watching documentaries. 

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  1. These are fantastic tips.

  2. Fantastic tips.

  3. Aaron 5 years ago

    This is a great read for all the entrepreneur out there!

    • 5 years ago

      Agree, Aaron. These entrepreneurs are pretty savvy at what they do and they speak from experience.

  4. kate 5 years ago

    Impressive share. Thanks for letting us know some thoughts of business skills.

    • 5 years ago

      Thanks, Kate. We don’t often think about Skills, but they are important.

  5. Tiara 5 years ago

    I am not a big fan of public speaking. I always feel like I’m going to choke or make a fool out of myself. This is such a great read. <3

    • 5 years ago

      Thanks for sharing, Tiara. Good luck with challenging and overcoming that fear!

  6. Yeu Doi 5 years ago

    Great tips! Success is a work in progress! We have to deal with the ups and downs of life. Your article is helpful for my entrepreneurship group. Thank you!

    • 5 years ago

      Thanks, Yeu. Glad you found it useful.

  7. Gennifer Rose 5 years ago

    Great insights! We all have our strengths and weaknesses and knowing where we need to improve is important in order to grow. Success is a process.

    • 5 years ago

      Well put, Gennifer. We all need to constantly improve.

  8. saidat 5 years ago

    I love the tip on doing the things that one is great at while outsourcing the ones that one really dislike.

    • 5 years ago

      Agree with you, Saidat 🙂

  9. Odette 5 years ago

    Some of these tips can be used by managers in established businesses as well.

    • 5 years ago

      Very true, Odette. Many of these entrepreneurs are managing fairly large companies.

  10. Candy Rachelle 5 years ago

    I absolutely love this post and the tips…esp from someone who’s in the process of starting her own business. Bookmarking this! Thank you…

    • 5 years ago

      Glad you found this useful, Candy!

  11. Courtney Andrews 5 years ago

    These are all great tips for emerging entrepreneurs!

    • 5 years ago

      Thank you, Courtney!

  12. Nati 5 years ago

    The insights were very informative! thank you for putting so much effort in making us aware of all there is to achieve success!

    • 5 years ago

      We all can learn from others’ insights. Thanks, Nati.

  13. Jennifer 5 years ago

    Really great tips on managing a successful business! I agree with Camille that you should first do the work yourself before you hand it off to someone else. I know it can get very exhausting and time-consuming with so much work, but in the end, I think it’s worth it!

    • 5 years ago

      Well said, Jennifer. Doing is learning 🙂

  14. Daniela Miovska 5 years ago

    These really are great tips! You can always learn and relearn, as long as there is a will to improve. One must always concentrate on what is he/she best in and to be able to try new approaches.

    • 5 years ago

      SO true, Daniela. Glad you found these helpful.

  15. Kaylee 5 years ago

    These are all great tips, I believe their is always room to improve and keep growing.

    • 5 years ago

      Spot on, Kaylee. Static is not good!

  16. chei 5 years ago

    Wow what an awesome tips! I always wanted to learn anything.

    • 5 years ago

      Thanks, Chei.

  17. priti 5 years ago

    I love the part where you say “why not focus on what you are best at”, so important

    • 5 years ago

      Agree with you, Priti. Something we all need to remind ourselves about.

  18. Sarah 5 years ago

    Great tips! Thanks so much as I’m always needing to improve.

    • 5 years ago

      Thanks, Sarah. Getting better is about having the right mindset, which you seem to do 🙂

  19. Nicola 5 years ago

    Wonderful insight, enjoyed reading this!

    • 5 years ago

      Thanks, Nicola.

  20. Gemma 5 years ago

    Public speaking is my worse fear.
    Boring book keeping is the one thing I wait until I get completely overwhelmed.

    Your advise looks great

    • 5 years ago

      Thanks, Gemma. Good luck with tackling what you don’t enjoy, but might not be able to opt out of.

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