Rose Castillo-Komoda
Stefania Curto

Embracing uncertainty, Imani Ribadeneyra takes a chance on herself, leaning into the risks to create a creatively fulfilling life.

Guided by a desire to live life on her terms, Imani takes a leap of faith. Read on to discover how she defines her own trajectory, the conversation with her mom that gave her confidence to face uncertainty head on and how she embraces the gap between where she is and where she wants to be.
Rose: Describe yourself in a few sentences. 

Imani: A New Yorker in every sense - ambitious, creative, hardworking, competitive. I love interacting with different types of people, and New York gives me the ability to go out and be able to do and see something completely different every single day. I draw a lot of my energy from people around me doing incredible work across industries and backgrounds.

Tell us a little bit about your background. 

A big part of who I am is defined by the bond I have with my Mom and sister. We are incredibly close, closer than I can even describe. In many ways it feels like we all grew up together. We didn’t live the perfect textbook life, but we figured life out together. My mom taught us early on that life was never going to be picture perfect, but you have control to make your life what you want it. Learning from an early age that I am powerful in my choices was really important for me. We are all so loving and supportive of each other, I wish every girl could grow up being surrounded by such strong, incredible and loving women.

There’s this anecdote from growing up I always look back to. My mom had this famous line she’d use with us anytime we asked her why she worked so much. She’d say “Do you like this house? Do you like your school? Do you like the food we eat?” and I'd obviously say “Yes”, and she’d say “Well if you want to give up those things, I won’t go to work. I can stay home with you everyday, but if you want to have this life I have to go to work.” This is my mom to a tee - loving, supportive, but most importantly, real. She never really cared too much about what people thought, she is who she is. It doesn’t matter what people think or how things are 'meant to be done', as long as you're doing the best you can, something I’ve totally inherited from her.

How did you find your way to media and marketing?

I went to NYU and was undeclared for the first 2 years of college. I was pretty artistic as a kid, but being a realist, I obviously knew I was not going to make money being an artist, nor was I even that good. I knew I had to figure out how I could use my creativity in a way that would allow me to be financially comfortable.

At NYU you had to take all of these general classes, and the classes that I became most interested in were anything involving media. I was drawn to this because of the way the media affects everyone. Everyone watches television, everyone uses their computer, everyone reads the news. To be able to understand more of why and how we are consuming things, or what makes certain things captivating to the masses, was really interesting to me.  

I always thought that I’d work for a magazine, but not long before I graduated, Facebook and social media advertising became really popular. When I graduated the more exciting opportunities were in the digital realm and things kind of shifted for me. I was still very interested in creative content, but didn’t quite know how it was going to manifest itself. 

After college, I worked for a startup which was fun and crazy, with all the business development and growth, it was your typical startup environment. There wasn’t a clear structure or titles, there was no real “boss” to define your work, which in a sense, allowed me to do whatever I thought was interesting. I was definitely working a lot of hours, but it was exciting having all this freedom and being part of building something from the ground up. 

What were the catalysts that led you to create Imani Creative Consulting? Do you recall the moment where you decisively made the decision to go out on your own?

After leaving the start up, I worked for a larger company doing digital marketing communication. While the company was a great place to work and I learned a lot, the rate at which I was learning and growing plateaued. I got to a point where I realized that I had no interest in having my boss’ job or the position ahead of that, and so on. None of it sounded fulfilling to me. The timeline of rising within the firm was clear, but also rigid. I thought to myself, even if I am getting promoted, they are treating me well, and for all intents and purposes, I’m on this steady trajectory of rising up the corporate ladder - Is this what I really want? Why am I waiting to have autonomy over my work and salary? Do I have to wait 20 years? Am I willing to wait?

It became pretty clear that I had two options. The first, would be to take the risk, bet on myself, and try to make a good living while creating a flexible and creatively fulfilling life for myself. The second option, of course, would be to stick with my stable 9 - 5 and keep progressing on the 'normal' track. Ultimately, I felt like the first would come with a lot of risk, but the latter would come with a lot of regret.   

At the end of the day, it was a conversation with my mom that really helped solidify my choice. I floated the idea of going out on my own to her and she basically said something along the lines of “By the time I was your age, I was divorced with 2 young kids and making less money than you. What are you afraid of? You, right now, are older, wiser, and more financially capable than I was. What’s the worst that could happen, that you’d want to go back? What's the best thing that could happen - that you never want to go back?”

This conversation, at an LPQ (Le Pain Quotidien) on the UWS (Upper West Side), made it real. People do things that are way harder than this under less advantageous circumstances. Having her say that made me realize that there was no real risk, probably just fear of the unknown or failure. 

I’m still young, I don’t have kids, and I don’t have any debt — I am super lucky that my mom paid for all of my education. Not to mention the fact that my skill set is digital, which meant that I didn’t have a lot of overhead.

Once I got over the fear of not having that elusive "stable trajectory", the opportunity to create the life I wanted right now felt super attainable. The reward outweighed all of the risks. 

How does it feel to take a chance on yourself? 

Scary, and also at times painfully awkward because of these self doubts I had; maybe this is uniquely a woman thing. I had lots of internal battles. “Do I really think I can do this? Am I just projecting to be better than I actually am? Am I overvaluing myself? Am I being obnoxious? Am I overconfident? Am I being completely naive?” These were the questions that I kept asking myself.

Being able to negotiate and really advocate for yourself, at least to me, is awkward. Every time I send a proposal I fear someone gawking at the price. Every time I try something completely new, like accounting (ha!), I literally feel like a fish out of water. Throughout this process, accepting myself exactly where I am has been beyond awkward, but also really fulfilling. Every time I overcome these little moments of self doubt I feel like I become more myself. Every day I feel like I'm getting better at it. 

On the serendipitous timing of it all...

The year I decided to go on my own, the start-up I helped build was acquired. When I left, I exercised my stock options and purchased stock in the company. I worked incredibly hard, was invested in them, and knew that if they did something in the long run, I wanted to benefit.  

About a month after I started my own business, the company notified us of the acquisition. Within 2 - 3 months, I received the stock option money. It felt really crazy, in the sense that I had helped them start their company, and to have this dividend come in just as I was starting mine. This made everything feel more concrete, like this little entrepreneur life cycle came full circle and it was my turn to build something for myself.

I learned a tremendous amount and gave so much in helping build that start-up. When it was my turn to take a chance on myself, all that work I did fueled my confidence. The timing was uncanny, just when income was going to be uncertain, the dividend really gave me a boost and made me feel that forging this path on my own was meant to be.

What were some misconceptions that you’ve had to push through in order for you to move forward and initiate this change? 

The people close to me were extremely supportive, but some in ancillary circles felt like it wasn’t my time and voiced their opinions on how "hard" it would be. I got a lot of “you’re too young to even understand what you're taking on”. There were definitely people who said “sure have fun but it obviously won't be sustainable”, or others “you have so much room to grow within the corporate world, why are you leaving”. Thinking I didn’t have perspective because I was young, that I wasn’t aware of what I was leaving on the table because I hadn’t worked for a company long enough. I thought well, if I stay in my comfort zone too long I’m going to live with a lot more regret than a missed bonus or promotion cycle. 

My naivete and inexperience benefited me in certain ways. I felt that I had enough time to fix this “mistake” if it went poorly. I can go back to a corporation if I need to, but if I worked for a company for 30 years and then I realized I wanted to go backwards, it would be out of the question. 

How did you find your way through the doubts? 

This is the kind of person I am - I’m like a light switch. Once I decide I’m going to do something, whether it’s a good or bad decision, I'm set on doing it. It’s like this tunnel vision occurs. When I realized starting my own company was something I wanted to pursue and it was attainable to work where I wanted, charge what I wanted, within reason, and still live my life to its fullest extent; I was committed. Everyday from then on, that I didn’t do some work for it, or take a step closer to doing it, I would feel this almost crippling anxiety; and full disclosure I’m not an anxious person. Most of my friends refer to me as the least anxious person they know. 

Either way, once I decided this was my path for now, I felt like I was wasting time any second I wasn't chipping away at this goal. At some point the anxiety and fear of regret overrode the fear of failing. 


Lessons on comparing yourself with others as you create this space for you to explore your interests, your purpose, and finding your rhythm...

I have 3 friends from college, we are super close, and all share characteristics of being driven and wanting to do well in our own fields.  One is a designer at Apple, the other leads a creative team at Pepsi, the other works at Facebook. 

Of our little female power crew, I am the only one who’s not working at a big brand name anymore, and sometimes this is tricky - How do I define that I'm doing as well as my peers if there’s no yearly promotions or corporate ladder to climb? What does success mean for me now? In some ways it’s knowing that I'm financially stable and creating freedom for myself is enough. In the end, my work and the way I carry myself have to be enough. And I have to truly believe it, because if I don't, no one else will. 

When I first started my career I could lean into the fact that I went to NYU, studied a certain major, took certain classes, had a certain GPA. This was brand recognition enough. When I was at the start-up similarly, I could lean into my title and the industry. Again, at my corporate job, I leaned into a brand name to give quick credibility with others. Other people may have a straightforward simple answer. Any time I feel self conscious about something like this I have to remind myself of the liberties that I have in my life; like being able to go on a run at 10 am on any day I want, or being able to work from London and see my sister for 3 weeks if I really wanted to. In creating my own business there are things that I am afforded, but a simple, straightforward certification of success is not one of them. I recognize that I gave that up, but I also gained a lot.


In the process of transitioning from working for a company to creating your own, what were some of the challenges you faced? 

Someone recently said something to me along the lines of - “Learn to embrace the gap between where you are and where you want to be, rather than let it freak you out”. This is something I’m working on constantly.

My website doesn’t look exactly how I want, I’m not working with all of the clients that I want, some of my projects aren’t as creatively appealing as I want. But I am sustaining myself financially, I am working with clients that I like, and I’m getting a lot of word of mouth recommendations. Trying to focus on the little steps and momentum, versus how much I have to go, is usually helpful. A year ago I just wanted to start, I just wanted to be able to make enough money to live by working on anything that came my way, just to push the momentum forward. Creativity and caliber of clients was secondary on some level. Now that I’ve done step 1, launching and building a client list, I can do step 2, expanding on the work I’ve done and taking on projects that spark more creativity -  I wouldn’t be able to do step 2 unless I did step 1. Taking it step by step, understanding and embracing the process and not freaking out about being far from my end goal helps me feel more grounded and less overwhelmed.

"Once I got over the fear of not having that elusive “stable trajectory”, the opportunity to create the life I wanted right now felt super attainable. The reward outweighed all of the risks."
On learning to embrace the fears and mistakes ...  

I got over the idea I was going to be comfortable on a daily basis. I accepted that this was not going to be perfect, that I am not going to be ready, that I was gonna fuck things up here and there. It was a lot easier to have this outlook of, well, that was a learning experience. I've started embracing the mistakes big and small as future wins.  

Once you accept these things are going to happen, that to some degree it is what it is, you learn and keep going. It's been super important for me to have a sense of humor and recognize that I am not a CEO with a ton of experience, I’m me, and that comes with lots of pros and cons.

What motivates and drives your ambitions?

I am someone who is very self-motivated, mostly driven by the fact that I have this deep desire to live my life the way I want, on my terms. 

I’m a very ambitious person but not in the sense that I want to make the most amount of money, build a huge Fortune 500 company, make the Forbes 30 under 30 list, or any of those accolades that have been ingrained in our heads; these are not super important to me. What’s important to me is having the flexibility to live the way that I want, to be happy, and to be challenged. 

The drive to grow my company is one thing, but the reason towards that is so that I can do things that are fulfilling, have financial stability, and to have experiences versus material things.

I also think about my mom. Her life was much more difficult than mine, with much less opportunity, and she has create a beautiful life that she loves. With a lot of determination and hard work, it can happen. The opportunities that I’ve had are so much greater than hers, so if she can make this beautiful life with less, I feel like I can probably do the same.

On feeling fulfilled…

There’s something to be said about creating a history for yourself, and the ones you love past, present and future. In the same way that my mom created a path that’s easier for me, her mom did the same thing for her. I feel really excited and powerful knowing that I can push these personal histories forward by creating success for myself right now. I feel very fulfilled and happy knowing that I am building on the success and hard work of the people that came before me and that my efforts are also going to be expanded upon. 

The idea that what I’m doing hopefully not only honors the things that people have done before me, but also contributes to creating opportunities for people that are going to come later is so fulfilling. It’s about being part of this life cycle, knowing that you are part of something bigger.  

How do you define success? 

Freedom and flexibility to live how I want and where I want. To be able to live, eat, dress and do what I want on any given day. That is not a luxury that many have. There are people who make a lot of money but they don’t have the freedom to live the way that they want. I was willing to take the risks on a stable income for this freedom. 

In what ways have you changed since the start of your journey?

I’ve become more confident in who I am and what I bring to the table. It’s really easy to label yourself based on what you do, especially in NY. People say I’m “X” and it’s their job title and it's not who they are. I think I've become aware of what my strengths are, and that also comes with figuring out what I'm not good at and knowing what to do with that information. There’s a confidence that comes with knowing your strengths and weaknesses.  

I’m also more trusting of myself. It’s really easy to make mistakes when you work for a company. There's a safety net within a team, and a boss, who’s decisions you are most likely following. It’s completely different when it’s just you. You have to trust that even if you aren’t making the right decision, you are going to be able to handle it.

How did you fully allow yourself to trust your intuitions?

I don’t know that I fully trust my intuition all the time, but when I do it usually involves me accepting that whatever happens is fine. Those dire moments when you are questioning everything, the details, is this perfect? No. To be honest, it never is. To get past this I usually end up asking myself, is this the best that I can do right now? If the answer is yes, then you just have to trust that and go with what you have. 

I often feel like working within the constraints of the present is really fun. If I'm doing the best I possibly can in the present, that’s all I can offer. If I choose to harp on what might be better in the future or what could've been done better in the past, that decision paralysis just completely hinders the present. If I feel like I'm not putting out my best work then it gets tricky, but as long as I’m putting in as much effort as possible to make it as good as possible, right now, then that’s all I have. It’s all anyone else ever has.   

What are you most grateful for from this process?

Confidence. It’s given me a lot of confidence and I'm very grateful for this. 

In the past my measurement of myself, how I was doing, was based on external factors. But for this, I’m the only person who’s deciding what is successful. It’s given me a lot of confidence to set big goals and keep myself accountable towards them. I’m not waiting for a promotion or for my manager to say you did a good job. I'm not waiting for someone else to validate me.

Where are you in your journey?

The beginning - not even scratching the surface, I hope! Where I am right now gives me a lot of runway, which gives me the flexibility to make mistakes, to discover. I’ve taken the first steps fully and have decided to forge ahead to continue, whereas maybe even 6 months ago I was still giving myself an out. I'm entrenched and know this is sustainable -- at least for a little while. 

There’s perspective, the experience has changed me enough that my experiences moving forward will be affected by it. I’m still in the beginning, but I’ve done enough where I know I’ve grown and changed forever.  

As you continue to evolve, what are your guiding principles?

One that I have been working on in the past year is being kind and patient with myself. It’s easy to tell yourself, you aren’t doing enough all the time. But being a little bit patient and kind to myself is something that I’m coming back to a lot and trying really hard to embrace. 

Something that is helpful is having people close to me that give me perspective. They remind me of how far I’ve come and how much I've done within the past year; it’s hard to have this perspective sometimes. It's hard to be patient, work hard and trust that it’s going to be fine. The outcome isn’t something that I can always control. But what's the worst that could happen? If I fail at anything I have to trust that I'll be better for it in the long run. 

How does chasing sunshine manifest in your life? 

In my daily life, I've decided to take a chance on myself. It takes a lot of courage and grace to take a chance on yourself, to be who you are and be ok with that. It takes a lot of courage to live authentically. 

To feel the end result of pure joy or sunshine, you have to endure a bit of struggle and rain. Something I circle back to a lot is that I can’t be brave unless I'm afraid, I can’t be courageous unless I have doubt, I can’t be happy unless I’m sad. I have to confront all of these contrasts and be accepting of both sides. It’s manifested itself in this way and hopefully I am learning to do it better everyday. Everyday that goes by the stakes get a little higher, but I also get a little more confident, a little more courageous. 

Is there an image that comes to mind that embodies chasing sunshine” for you? 

This vision of myself waking up in a home that I am happy to be in, with people that I love, being challenged in some way, being able to be active and exercise, and having time to unwind. This idea of a balanced life. Acknowledging and recognizing what I’m grateful for but also holding space for improvement and the drive to want more. 

Working really hard and being challenged is funny in that it inevitably comes with some uncertainty, but ultimately leaves me feeling more certain with myself. 

For those who are in the midst of discovery and finding their sunshine, what are some words of wisdom that you’d share with them?

If anyone is looking to make a change but feeling unsure of themselves, I would encourage them to really dig into what they're afraid of and face that head-on. For me the desire to be courageous and adventurous in my career and life came naturally, but it was a lot harder to accept that I had to feel scared and uncomfortable to get there. Get uncomfortable and embrace the scary stuff, the good stuff is on the other side.