Self-Coaching to Overcome Entrepreneurial Challenges

By Caroline Langston


Entrepreneurship is not an easy undertaking, even in the best of circumstances. It is daunting in the early stages, and challenging in a multitude of different ways as your company grows.

As an entrepreneur and owner of a startup myself, I understand the issues you may be facing now. And as a business and personal development coach, I am constantly looking for the way through and for the solutions to keep moving forward with my clients–especially when there are challenges.


I want to reassure you that you are not alone, and share some useful tips, exercises. and self-coaching techniques to help you overcome the top challenges you will face as an entrepreneur and startup founder. Below are the primary areas of challenge, and what you can do to move a step forward towards your goal.



Obtaining funding can be tough and a large stressor, as can budgeting and managing your capital. To gain funding, you may need to reach out and network, be resilient, and present your ideas in a confident and convincing manner to the right people.  After the first contact, you need to be able to make your pitch and then deliver. 

When times are tough, telling yourself “you can” is extremely important for your internal belief system and attitude. Create a plan based around what you can control with regards to your finances and funding. Work out a way forward to your next goal, however small it may be–whether it’s reaching out to five new funding/investment partners, or becoming more confident and practicing your pitch until it’s perfect. These steps will help you with motivation as well.


Time Management and Prioritization

Are you fairly rigid and able to stick to a schedule? Do you get distracted and then end up not doing what you really should be doing because something else is more exciting?  Setting yourself a schedule and sticking to it can help, but knowing when deviation from that schedule may be beneficial is also useful. So how do you decide? 

Working out your priorities helps. Are you a list maker? Do you practice the Pomodoro Technique to focus on a task? (This technique allots timed, uninterrupted 25 minute blocks to projects or jobs you need to complete.)    

Ask yourself: how essential is the task you are doing, and how does it fit into your short, medium and long term goals? Work out how you will prioritize, when to stick with your list, and when it is best to change direction. Evaluate the benefits of changing direction and go for it when you are sure it is the very best use of your time in terms of  achieving the most important goals.

Business Growth

When, how, how much? These questions apply to almost every facet of being a founder, and can be linked with money, management or your ability to delegate. 

Making decisions about when and how to grow is difficult when you are on your own. Working with a partner can be easier if both of you are well-aligned, but can actually be harder if you are not! 

Take off your “technical hat” and put on your “management hat”. Think about how to manage a period of growth and what the potential outcomes will be. It is important to consider all possible results, both positive and negative. Think about people, money and other resources you will need. Do the costs outweigh the benefits?  

Try to discuss your situation with a third party.  Sharing ideas with a trusted and experienced business leader or mentor can help you understand the right direction to take, and push you to the next level. And equally or perhaps more importantly–their input could help you avoid mistakes or steer you away from choosing a growth direction which may not work.



Self Doubt

We all doubt ourselves from time to time, but as a new business leader you need to focus on what you have, what you can do and work out what motivates you. Practicing mindfulness (focusing on the here and now, in the moment) is a useful strategy for some, enabling them to focus on what can be done. Incorporating self-coaching to work towards a positive goal (“I can, I will”) can also help you mentally move in a better direction.


However, it’s important to lean on other people from time to time as well. Ensure that you have a support network. You may have different resources for different areas of your business–friends, family, external advisers, mentors, coaches–they can all help. Remember, it’s okay to not have all the answers. Sometimes externalizing and talking it out with someone can help with internal resolution and direction.



A common saying in the startup world is, “If you have a job you love, you will never have to work another day in your life.”  I know and understand this. I truly love what I do. It is part of me and does not feel like a job. However, being able to step away from everything is important. Time taken just for you, or spent with friends and family, is essential. 

Self-care for survival is the most important part of starting up, and goes a long way toward ensuring you remain robust. Go for a walk, do some exercise, watch a movie, meditate. Taking time to do whatever relaxes you to truly replenish the fire for your business is far more beneficial than working until a burnout.

Where we are in the world today is because of people who had the courage to wake up, do something different, and take a chance in a new direction. This does not come without its challenges, but it is important to remember to create a journey for yourself that is just as fun and satisfying as the destination.

About the Author

Caroline Langston is the Founder of Successful Consultants Limited, a Coaching and Personal Development company in Hong Kong. Caroline worked within recruitment for 11 years across the world making hires from Senior Managers to Global Senior Executives in Engineering IT, Digital and Technology. This included working with global companies, entrepreneurs and business owners. In 2019, she decided to work for the candidates and set up her own company dedicated to coaching people for success in their careers and lives. Caroline is degree qualified with further certifications in Neuro Linguistic Programming at Master Practitioner and Coach level. She has completed 60 hours of training at International Coaching Federation (ICF) standards and loves working with a range of people and companies, especially startups and new businesses, helping them grow.


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