We caught up with the brilliant and insightful Rashidat Odeyemi a few weeks ago and have shared our conversation below.
Rashidat, thanks for joining us, excited to have you contributing your stories and insights. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.
The biggest risk I’ve taken was leaving a great career to pursue a yearning that I had no idea where it would take me…
Like most professionals, I went to college, got a degree, and I was fortunate to get a job in my field just 3 months after graduation. But it started in my first career position, and then continued into my second, and I even thought I’d quit it all a become a dog walked during the 2008 recession, but my career pulled me back in then, too. I kept going back to my career in fashion because I was good at it, I made good money, and my life was stable. But I also would think “there’s got to be more to it than this!!” It was this crazy feeling where nothing was inherently or explicitly bad, but I also wasn’t happy.
Fast forward to 2016, I was making my last payment on my last student loan… As I made the click for that payment and became debt free, I realized I didn’t NEED much of anything. I could finally prioritize what I WANTED. So, I went looking for more even though I had no idea what “more” looked like. I went on the Dave Ramsey show and did my debt-free scream. Then I quit my job and did international missions to 13ish countries for a little more than a year and I attended a leadership academy in Spain for 9 months. And through all of that, I figured out what more looked like for me. I wanted the autonomy and freedom to live life and make money on my own terms without being tied to a specific location. I wanted to build my own career that allowed me to show up fully and be fulfilled. I wanted to do something that I could feel connected to the impact it was making for a purpose greater than me.
Yep, I’m a Millennial – LOL
But I figured out how to do it – how to live the freedom I was looking for. Leaving a great career might’ve been the biggest risk, I’ve ever taken, but it’s also been the biggest reward!

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
My former career, as I said before, was in fashion specifically as a technical designer. But as I was on my journey to find “more” I had someone say to me “Hey, you should be a life coach.” At that point, I’d never heard of a life coach and had no idea what they did, so, frankly, I ignored the suggestion.
But as I traveled, I realized that I loved being the accountability, encouragement, and sounding board to others looking to change their lives. But I still didn’t really get it – it never really crossed my mind that I could make a business of helping people strategize, plan, and reach their big goals and dreams until a friend asked me to help her do exactly that.
We started with mapping out her long term vision, breaking it down to focus on her top priority, and setting up routines and habits for her to execute her plans in manageable chunks that built into the goals she was working on. She was amazingly grateful for all my help, but I was just as grateful to her too because it helped me see the need for such services. It allowed me to see that I could help people with 2 things that most aren’t adept at using – vision and organization.
Hence, in mid-June 2019 I started my business as a life coach, helping people create a vision and get organized to create a 5-star business and life through these two products…
In the first product, I help visionaries who want to do it all create & implement a strategic plan without burnout so they can accomplish all their goals despite life’s interruptions using my Dream Strategist method. It’s called the Productivity System and I affectionately say this is the person who has ideas for days but can’t keep up with themself! It’s a course and community, with the option to upgrade to 1:1 coaching sessions, where I guide them through getting good at articulating their life priorities, creating a long-term & short-term vision, and them implementing routines, habits, and manageable chunks of “do-time” to execute their goals for the year. What makes this different than anything else out there is that most people get freaked out about making a long-term plan because it seems so hard to think that far in advance. I make that process easy and that allows them to put a destination in their life GPS. With a destination, it simplifies decisions, gives them focus, and makes it easier to get stuff done. This system makes even the WILDEST dreams possible.
In the second product – which is specifically for multi-passionate entrepreneurs and creative entrepreneurs – I help them organize their business so they can pay themselves and hire help. With the pandemic so many people “just started” a business and I LOVE IT! They didn’t let the fear of the unknown hold them back! But now that they’re a year or two in, they’ve made some sales and they’ve learned so much that now it’s time to set up strong foundations and get strategic about reaching their goals (because scaling, paying themselves, & hiring help doesn’t happen by accident!). This is the person who left their traditional 9-5 or is trying to make their side hustle their main income because they want more freedom in their lives. But right now they’re tied to their business working harder and longer than they ever did in their 9-5. They want their business to empower the freedom they’ve been looking for and the Evergreen Business Accelerator will help them do that! This course and community, again with the option for 1:1 coaching, will help create and implement a strategic plan for growth so they can achieve their goals. While most products focus on getting their brand and marketing in place the Evergreen Business Accelerator sets entrepreneurs up to manage all 6 areas of their business and accomplish their goals all without burnout or working longer hours. This is what autonomy and freedom are supposed to look like!
I’m most proud that I took that risk to leave my job! It’s far from easy to leave stability, but it’s been so rewarding! And I’m even more proud that I’ve created two products that help others who are going through the transitions I’ve gone through. Past me is proud that we’ve made the most of figuring it out and can make it a lot easier for others to successfully make that transition.
Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
The biggest lesson I had to unlearn was how to stop being an employee and start being a CEO.
I’d been a corporate professional for longer than you can believe… When most people had their first jobs in McDonalds, I remember my first summer job was as a receptionist at a non-profit at age 14. So by the time I decided to become an entrepreneur, I’d been an employee for almost 20 years! Yes, I’d always been entrepreneurial per se, but it’s a whole other ballgame and mindset change to be doing it all on my own. Being a great employee was engrained so deeply in me that when I started my business I had unrealistic expectations about… everything.
I tried to wear all the hats all the time and that quickly turned me into a burning-out, work-a-holic CEO. I hadn’t figured out how to zoom out and look at the big picture and vision, choose priorities, create a plan, and then zoom back in to focus on and execute said priorities & plan. Instead, I was treading water. I couldn’t see the forest for the trees! And IT WAS SO TIRING! I was constantly jumping from task to task and felt I rarely finished anything, always trying to deal with emergencies, stretching my capacity way too thin, and putting my life on the back burner all in hopes that I could finally get far enough ahead in my business that the craziness would level out.
I could use vision and organization in life, but I needed to take those practices to the next level and use them in my business as well, but it all had to start with changing my mindset on these 3 things:
1. I had to get over my scarcity mindset, stop trying to DIY stuff, and pay for business mentorship and coaching. It’s this weird thing where we know it’ll make our lives easier (and more profitable) to get help, but our culture has this stupid undercurrent mindset that we want to be the outlier – the one who did it all on our own without help. And it’s complete BS! Business coaching took my life coaching to a whole new level! Now I have a whole team – a business coach, a therapist, an entrepreneurial community, and any other help I need so that I can be my best me for myself and for my family and provide an amazing service and product for my clients. Paying money for mentorship and coaching is not a waste. Instead, it’s a huge return on investment.
2. I also had to get over my mindset blocks about selling. I had to realize I’m not a sleazy salesman. I have absolutely no need or want, for that matter, to see to someone who won’t actually use or benefit from my products and services. Instead, I want to make life easier for others by sharing the things that changed my life and will change theirs for the better too and that’s the complete opposite of being a sleazy salesman. It’s my honor to serve people and rather than selling I get to listen to their story, empathize with their struggles, and share how I can help them come out victorious on the other side. If it’s a good fit, then I get to invite and offer for us to work together, but I never have to convince them to take part in something they don’t already want for themself. This mindset change has made it so much easier to take up space in the market and share my products & services with people.
3. Hi, my name is Rashidat and I’m a recovering work-a-holic. 😅 I mean even before becoming an entrepreneur it was my default to take responsibility for more than my fair share and do everything in my power to not only accomplish it, but to make it perfect. I think I’ve always known it wasn’t healthy, but really didn’t know how NOT to do it. I had to get, and still am, obnoxiously intentional about scheduling rest and FUN. So much so that I call it my Anti-Super Hero practice and I teach it in my program. This practice helps me create a work/life balance that sets me up to be successful AND happy.
I needed this freedom of mind to get to freedom in work and life. As an employee, I could fly by the seat of my pants on these things, but as a CEO I have to be crazy intentional to unlearn those tropes and take hold of the freedom and autonomy I wanted.

Can you tell us about a time you’ve had to pivot?
I have made so many pivots! Most of my life is pivots! 🤣 I used to think that maybe I had an issue with commitment, but then I had a revelation…
I wasn’t changing my end goal, I was simply pivoting my path to get there. I started thinking about it like a GPS. You need an address in the GPS so that it can create a path. My address for where I’m taking my life and business is my vision. But on the way there, there are always obstructions, roadblocks, and redirects – a lot of times I’m the obstruction, roadblock, and redirect. I had to get out of my mind that there was a perfect path or that I could have everything perfectly figured out from the beginning without any derailments because that was not realistic. Instead of a perfect path, I learned to ride the waves and keep going.
I’ve pivoted where I’ve wanted to live so many times. I’ve lived in 6 different states. And in my last pivot, I thought I wanted to move to Costa Rica. After a year of living there, after selling my car, and starting to get settled I realized it ultimately wasn’t for me. So I came back.
The first business I started was a non-profit. I thought it’d be perfect because I was looking to do something more fulfilling. After I got into it I realized that I really didn’t have as much passion for that topic as I thought and I closed its doors.
These are just 2 of many times when I changed my mind. I used to beat myself up about it because I felt like I’d made a mistake. In hindsight, I’d sometimes feel like I should’ve known better. But now I realize I would’ve never figured out what I know now if I hadn’t taken the risk and tried.
Another thing I teach in my program is about learning to articulate our character. It’s super important for tearing down limiting beliefs and self-affirming our worth and value so we can move forward. Of the top 3 ways I describe my character, my favorite is to describe myself as wise. I love it because when I define it has nothing to do with getting things right or perfect and everything to do with making mistakes, taking risks, and stepping out trying, and learning everything I can about who I am and how I want to show up every day. I think what makes me wise is that I’ve learned to have fun rather than fight the waves. Rather than being stick-stiff on a surfboard trying to avoid falling off, I’ve learned to ride the wave and if and when I fall off I know how to get back on the board. In practice, I’ve learned to give myself some grace, get a nice drink, and take in the view.
Contact Info:
- Website: RashidatO.com
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