Letting Go of Should by @makedapenycooke

by Makeda Pennycooke | Featured Contributor

When you’re an entrepreneur it is easy to get lost in the sea of advice from Letting Go of Shouldall the experts out there. Everyone has an opinion about how you “should” be running your business and what you “have to do” to be successful.

I’m not saying getting advice from others who have walked the road ahead of you is a bad thing. What I am saying is that when following other people’s advice results in you losing yourself then you have a problem.

It’s a problem I know well because on more than one occasion, in the year that I’ve been running my business, I’ve gotten sucked into doing it the way I should and forgetting about what feels most right for me.

Without fail, every time I have done what I should without considering whether it really worked for me, I ended up failing. Success is coming to me as I learn how to let go of should and give myself permission to do things my own way. Here are a few of the lessons I’m learning.

Know what’s right for you

In the entrepreneurial world, and especially in the online world where my business resides, there are some rules that, generally speaking, work for everyone. But you still have to take those rules and filter them against your personal goals.

Hold them up against what you want to accomplish and HOW you want to accomplish it.If an idea “guaranteed” to work causes you to feel icky on the inside or compromises one of your values, it’s not worth doing it. No amount of success is worth feeling like you have to sell your soul to get there.

Understand every journey is different

Your journey as an entrepreneur or business owner will be different than the person down the block from you. You have to embrace your own journey and allow it to unfold naturally.

If you try to write the details of someone else’s story into your own, you lose the wonder and meaning inherent in your own story. What worked for one person may not work for you and that’s okay. It doesn’t mean that they’re right and you’re wrong, it simply means that your journey, your story is different and that is actually a good thing.


Finally, your business, your clients or customers, and your family and friends all win when you are simply YOU. Stop trying to be a copy of everyone else and instead be the inimitable original that you are.

Let your originality shine through in your business. You get to decide what success will look like for you. You don’t have to follow the experts’ rules; you CAN play by your own rules and still win.

So for the rest of year, give yourself permission to do things your own way.

Here’s to letting go of should and rising into your greatness!


Makeda Pennycooke, Women’s Leadership Mentor and Coach

Makeda PennycookeMakeda Pennycooke is a mentor and coach specifically supporting women leaders. I have 15+ years experience leading and developing teams, including six years serving at the executive level. I believe women are being asked to play by rules that don’t work for them and many women feel stuck living a life that isn’t right for them. After spending too many years letting other people’s opinion decide how I should live and lead, I am now committed to empowering women leaders to redefine leadership on their own terms.

In my spare time, you might find me curled up with a book in my favorite recliner; wandering around in pursuit of beauty behind the lens of my camera; or attempting to further my budding relationship with yoga.

I believe chocolate makes everything better, and life should be filled with moments that make your heart sing. I love the ocean, sun-kissed days and a good cup of steaming hot tea (always tea, never coffee). I can be found sharing tips and inspiration for women leaders at www.makedapennycooke.com Let’s be friends Twitter | LinkedIn | Facebook

Share :