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3 Mindset Shifts Every Small Business Owner Needs to be a Confident CEO

Imposter syndrome? Asking for what you want? Being assertive?

What about having the tough conversations, speaking up for what you want, setting boundaries…

When our business grows, certain things become easier… but many times we’re faced with tough mental blocks we have to work through, to fully step into our CEO shoes.

Friends, we’re heading into territory many business coaches and mentors call MINDSET! These are 3 mindset shifts I’ve personally made to be a confident CEO and act like the CEO I need to be, to look out for my business and myself.

Mindset Shifts to step into your CEO shoes

Starting my business I had common mindset blocks I’m sure you can relate to on some level…

  • Imposter syndrome
  • Scarcity mindset
  • Jealousy

Scaling my business, I noticed those 3 mindset blocks will always loom in the back of my mind, but I had other mindset blocks that came about. Other mindset blocks that I dealt with were…

  • Feeling deserving
  • Comparison
  • Shiny-object syndrome

I could write a huge post talking about ALL the mindset shifts I needed to overcome – hah! Today I want to trim it down to the 3 biggest mindset shifts I faced as I scaled my service-based business and owned the fact that I am a CEO.

1. Cute doesn’t get things done

I scaled my business by hiring a team member, winning larger projects, and helped clients bring in thousands of dollars through copywriting. I couldn’t be “cute” anymore. My “cute” personality was actually holding me back, A LOT.

To put it simply, I realized that:

  • “Cute” doesn’t do business.
  • “Cute” doesn’t get taken seriously.
  • “Cute” gets overlooked.

I thought I was being humble when I played ‘coy’. I downplayed my skills as a brand strategist and copywriter, leading to downplaying my authority and expertise.

The more I play the *cute* card, the fewer people take me seriously, which is a cycle I would throw myself in. I didn’t take myself seriously because I didn’t feel like a CEO, like I hadn’t made it yet! It was all in my mind what a CEO was “supposed” to look like and for me, I didn’t look like one!

READ: 2019 Business & Marketing Lessons

Because I didn’t take myself seriously, no one else took me seriously and thought I was playing business. In actuality, I had clients in English and Spanish from around the world, was giving workshops in English and Spanish, and more!

The shift: When I realized that I AM the boss. I AM the CEO. I brought in clients, helped them achieve visibility and sales, and grew my business to a 3-person team!

two women talking while looking at a laptop in front of a window

2. Head down & work hard is a myth

As a first-generation Asian-American woman, I grew up being told by my parents that I needed to put my head down, don’t make a fuss, and work hard. I took this belief with me when I worked in a full-time office job. Then when I left, I took it with me into running my business.

Many Asian women deal with the stereotype of being quiet, dismissive, passive, and docile. I grew up shy, passive, and was considered a “doormat”! I adopted this work ethic from my parents alongside the Asian woman stereotype. Because of this, I barely spoke up for myself and had a hard time setting my boundaries.

If you know – when you don’t set boundaries or protect yourself, others will push their boundaries and limits with you. This comes in the form of clients pushing boundaries, collaborators, and people who want to be in the same spot as you!

READ: 27 Business Myths, DEBUNKED

On top of my mindset block of acting “cute,” unconsciously playing into the stereotype, and adopting this work ethic – a lot of clients, leads, collaborators, etc. acted like I was a “little Asian girl” who “played” business. When I asked for contracts, emails of written proof, and business meetings, people brushed me off.

The shift: If I’m going to do business, I will ask for contracts, email chains, and more to protect myself. I won’t make a fuss, but I will ask for certain things that businesses require to do business – because I am running a business! I’ve also learned that if someone doesn’t respect these requirements, I will not work with them!

3. Assertive doesn’t mean bitch

Asking for what you want, asking for clarification, and expecting excellence is not being a bitch. What this means is you are clear of what you want and by asking for it, you are closer to receiving it!

As my business grew, my fear of being called a bitch or overly bossy was constantly holding me back. I was afraid to I would be…

  • Annoying someone
  • Needy
  • Asking for too much

Because of this fear, I never told people what I wanted, needed, or expected because I was terrified of displeasing them.

READ: Most Important Lessons in Entrepreneurship

Truly, the root of this problem is people-pleasing tendencies. My fear of making someone uncomfortable made me hide. I hid from my own power, I hid from my voice, and I hid from success because I didn’t want to make someone uncomfortable.

The shift: I realized to gain visibility, run my business, and do what’s best for me, I needed to use my voice and stand up for myself! I need to protect myself, this business, my work, clients, ideas, time, energy, AND money. My being assertive, I help my business grow.

Cassandra of The Quirky Pineapple Studio scrolling on her laptop and laughing in an office

3 Mindset Shifts for Small Business Owners

We have plenty of mindset shifts in entrepreneurship and business ownership! They never stop and the more you grow your business, the more these shifts will come up in different situations in your life. The 3 biggest shifts I made to confidently be a CEO of The Quirky Pineapple Studio were…

  1. Stopped being the “cute” business owner and owned my role
  2. Protect me and my business, and not being afraid to do so
  3. Use my voice and ask for what I want or share when I don’t want something

These 3 shifts have been a catalyst in moving The Quirky Pineapple Studio forward. Since actively working on these blocks, we’ve been able to close higher proposals, bring on another team member, and streamline our marketing strategy!

What 3 mindset shifts have you made in your business to be a confident CEO? Were any of these similar to yours? Send us a DM on Instagram @thequirkypineapplestudio to chat about it!

*Want to learn how to USE YOUR VOICE and get more visible? Schedule a free Clarity Call with us to learn about the Use Your Voice 4-month Mastermind for service-based business owners who want to make more impact and share their message.


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