Boost Your Entrepreneurial Self-Esteem - The Oily Story
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Boost Your Entrepreneurial Self-Esteem

If you’re in business chances are you’ve compared yourself to other businesses, whether they’re a direct competitor or not, and chances are your self-esteem took a hit.

If you’re like 99% of us out there, you’ve judged yourself harshly, played that old tape that says you’re “not enough”, “who do you think you are to want a successful business”, and “you won’t stand out among the rest.” How unfortunate that many entrepreneurs fail because of their self-limiting beliefs.

Doing a SWOT analysis requires honesty with yourself, comparing your business to your direct competition (in a non self-punishing way), and willingness to accept what you uncover so you can change and improve. It’s a tool meant for you to grow so when examining the four components, remember, this is not a painful process to uncover everything that’s wrong – this is a self-love exercise for your dream.


Do you know what your Unique Selling Proposition is? Look for something you’re doing differently or better than almost anyone out there – here is what we’re doing and it’s been a game changer. Find what you love doing in your business and find a way to put a spotlight on that special something. Here are some prompts to help you find your Strengths…

  • List, in detail, everything you do in your business.
  • Detail your processes from beginning to end and look for where you’re a cut above the rest.
  • Where else do you go above and beyond? Is client care something you excel at?
  • Is creating new programs for clients something that comes easy to you?
  • What do your clients say about you? Look at your testimonials for commonalities.



I can’t say this enough – The weakness component isn’t meant to tear you or your business down. Use it as a springboard to propel your business forward. Once you become aware of your weaknesses, you need to accept them before you can take action to change them. Secondly, remember that changes take time and your weaknesses won’t miraculously disappear. You’ll create an action plan (we’ll talk about that below), and one step at a time you’ll improve. One huge key to this is being completely honest with yourself and how you show up in your business. Here are some ideas to help you uncover your weaknesses…

  • What does your competition excel at that you don’t?
  • Where do you fall-down in your business?
  • What are the important tasks you keep putting off that never get done?
  • How are you self-sabotaging? Do you have shiny-object-syndrome? Are you easily distracted? Do you lack discipline?
  • What have some of your client’s complaints been about?
  • Are you behind the times in technology?
  • Remember to stay in gratitude while you’re going through this exercise. It will show you how very adaptable you are to growth and self-evolution.



Growth can show up anywhere, not just in your bottom line. Can you recognize opportunities or do they usually get pointed out to you? You don’t have to know everything in your business and you don’t have to do it alone. Do you have tasks that overwhelm you either because you don’t know how to do them or simply don’t have the time? Look for support, whether it be from a bookkeeper, virtual assistant, sales strategist, web designer, or business coach. What are some of your opportunities to grow?

  • Can you identify where you’re leaving opportunity on the table?
  • Are you able to expand your network?
  • Would you be willing to step out of your comfort zone to seek out an opportunity?
  • Can you commit to building your skill set and shifting your mindset for a half an hour a day?



Having a 360˚ view means you’re prepared, so dive in and examine what some of your threats could potentially be. The list you’ll prepare isn’t meant to scare, intimidate or paralyze you. Using your threats as a guide to self-care, growth, and to develop a plan is one of the keys to success. Look at every area of your business and take an exhaustive inventory of how you’re showing up. Are you dedicated, always on time, creative, resourceful, seen as the expert in your field? In addition to looking at what your competition is doing, what are some of the threats that could send you on a downward spiral…

  • Negative self-talk. This is a business killer.
  • You’re overworked. You may need qualified help.
  • Procrastinating. If you’re cleaning the microwave when you should be mapping out your next client meeting that’s a clear sign.
  • Self-sabotage. Putting aside tasks that will move your dreams forward.
  • …I could go on and on.


So where do we go from here?

Here are 3 steps you can take, right now.

  1. Grab a pen and paper (no typing), and make your SWOT lists. You can take as much or as little time as you like. I recommend taking 20 minutes right now, set the timer and spend 5 minutes on each component. In the following days you’ll find yourself continuing to take inventory so take notes when your thoughts come to you and add it to the necessary component.
  2. Next to each item add specifically how you would like to improve or change.
  3. Then, detail the action of how you will accomplish each.

For example, you may have:

“Weakness: disorganized and would love to get rid of my shoebox full of receipts.”

Action: “Create system (with details) to process receipts”, or alternatively “Hire a bookkeeper.”

If you’ve been specific and set timelines then by the end of your 3 steps you’ll have a clear direction of the actions you want to take in your business and more importantly, you’ll appreciate how fantastic you really are. It may seem like an awful lot of work and it may not be easy, but you will reap the benefits in the end. You’ll have incredible clarity on how you show up in your business and how to recognize when you’re trying to put sticks in your own spokes.

Want to try the SWOT Analysis exercise? Send me a message to to share how this changed your life, and your business. 

by Eileen MacDonell


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