A decade is a lifetime in entrepreneurship. Back when I started my company, I was a bright-eyed recently graduated 24-year-old, engaged to my college boyfriend, brimming with optimism and unyielding determination. 10 years on and I'm still resolute in my pursuit, despite many unexpected pivots along the way. It's been the best journey yet and the thing I'm most proud of. My only regret is not having had the humility to ask for help–a coach, a mentor, a business role model–until a few years in.
As such, I'm sharing the 10 lessons I've learned through the years as atonement for my less-savvy twenty-something self. I hope it helps, and if you still have questions, let's talk online.
1.Prioritize Your Own Health and Happiness.
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I always believed that entrepreneurship would be my vehicle to freedom. Executed thoughtfully and with care, it can and should reinforce your lifestyle, ideals, and how you want to contribute to the world. When I speak of freedom, I'm not referring to the version glorified on social media. I'll be the first to admit that much of my day-to-day activity includes fulfilling requests made by our clients and my team. So, the social media version of being your own "boss" is a false narrative. Instead, seek the type of freedom that creates a space for you to always work from a place of authenticity, and allow that work to act as an extension of how you see yourself in the world.
2.Create Your Own Definition of Success.
For years, growth looked like a beautiful office with chandeliers, high ceilings and a chalk wall (because...millennials, duh). I made it my reality and delighted in it for a bit. But once I "had it all", I realized I was chasing society's standards of what an established agency should look like. I had grown attached to superficial definitions of success by watching my competitors–without having any clue what they were bringing in monthly or what kept them up at night. I lacked meaningful measurements to draw comparisons from – the Internet will do that. Once I spent some time introspecting about my business, it became crystal clear that my utmost desire in life is to contribute meaningful work to the world and to create opportunities for others. Since then, I wake up every morning full of disbelief and amazement at the stories we get to tell each day.
3.Seek Mentors and Always Know the Ask.
One day, you'll look up and realize that it's up to you to seek and find inspiration and to hold yourself to your promises to others. This can be problematic because there's always a new way to be more efficient and there are constantly new ways to innovate. A mentor should hold you accountable and ensure you're always refining your skills. But the relationship should be mutually beneficial. Be thoughtful about how you add value to the life of your mentor and always be prepared prior to meeting with them. Know what the asks are and what you hope to gain during each encounter.
4.Continue Developing, Growing, and Learning.
In addition to mentors, I've enrolled in business development programs (Goldman Sachs 10,000 Small Businesses was one). If you skipped business school and went right into entrepreneurship, I can't stress enough how important this is. The truth is, some of your competitors may not offer an exceptional product or service, but have the advantage of a greater business acumen. Developing your business skills helps you to scale up or down based on business performance, not emotions. For example, I've had up to six full-time employees, down to two and back up again to six. I've realized that growth doesn't always have to be linear. It can look like expanding on your existing services and offerings. You can increase your monthly fee or add additional services to existing accounts. Ultimately, growth requires investment, which can feel risky, however worthwhile.
5.Be Ready to Sacrifice.
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By 30, I was on my way to divorce while being forced to face some hard truths about my personal finances. I had neither traveled much nor cultivated new friendships beyond my college peers. I'd put everything into my company and I had missed out on many adventures and personal growth opportunities as a result. What's still true is that entrepreneurship can be lonely, so be ready to commit to radical self-care. So many of your personal and professional highs and lows will be determined by you, you alone and (if you believe) the God or Goddess you serve. The upside is that sacrifice can yield a life from which an abundance of joy, balance, and options flow.
6.Ask for What You’re Worth.
Through the years I've received some pretty amazing offers for full-time employment on political campaigns and within corporate organizations. In order to say "no" with confidence, I had to increase our rates so I'd sleep well at night feeling valued. However, it wasn't until year five that I added myself to our payroll. Again...nothing worth having is without sacrifice. I wish the 25-year-old version of myself had the confidence that I do in my 30's to fight for me, my team and my contractors the way I do now. Don't get me wrong, the pay gap still exists. I'm constantly reassessing our value proposition and trying to set a new standard for women who look like me. Frankly, we're taken advantage of the most in business. But it's a wonderful time to be alive. We have access to thousands of data points and digital content to allow our work to speak for itself.
7.Make Mistakes. Revel in Them.
It wasn't until year five that I enrolled in a business development program and acquired many of the tools and resources I needed to structure my back office in a meaningful way. As you can probably imagine, mistakes tied to finances, operations and administration are often the most costly. However, if you asked me today to get a business up and running within 48 hours, I'd gladly accept the challenge. The mistakes I've made through the years forced me to sit down, analyze, and ultimately continue to develop better ways to do business. I am grateful for that.
8.Stay Networking.
When we initially launched, our team committed to three networking events per week. Yes, it was exhausting. Yes, it paid off. Most of the contacts I have now are people I met in those early years. I never tire of picking up the phone and hearing, "I met you many years ago…" There is so much power in putting yourself out there. Stay open to the possibilities of budding relationships–they can flower and bear fruit.
9.Lead with your Heart, and the Money will Follow.
I kid you not, for every phase I've gone through in life personally, there's been a campaign or client I was able to channel that energy into in a positive way. In recent years, we've been able to shape dozens of stories around women, health, equity, access, community development and more. This isn't always easy when you're just coming out the gate. Once you become confident in your ability and certain in your values, you won't even blink at the opportunities that aren't aligned with you. I firmly believe in the law of attraction and Medley is proof.
10.Play to Your Strengths.
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Recently, a friend encouraged me to slow down on acquiring new skills and focus on what's right in front of me. This became an opportunity to reflect on the past 10 years, while nurturing the best area to build upon over the next 10 years. What she was referring to was my need to cultivate my leadership skills. I'm grateful for having been able to steer this ship for so long, but my company only grows if I grow. As mentioned, I've always seen entrepreneurship and leadership as a path to freedom – I was being called "bossy" in kindergarten (before Beyonce and friends banned it). But good leaders grow both themselves and others and are constantly modifying their style of leadership.
Play to your strengths. That's how I plan to spend the next decade.
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Answers have been edited for context and length.
xoNecole: How did the pandemic lead to you leaving the cubicle?
Randi: I was becoming stagnant. I was working in mortgage and banking but I felt like my personality was too big for that job! From there, I transitioned to radio but was laid off during the pandemic. That’s what made me go full throttle with entrepreneurship.
Gabrielle: I moved around a lot for work. Five times over a span of seven years. I knew I needed a break because I had experienced so much. So, I just quit one day. Effective immediately. I didn’t know what I was going to do, I just knew I needed a break and to just regroup.
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Randi O
xoN: Tell us about your journey after leaving Corporate America.
Randi: I do it all now! I have a podcast, I’m an on-air talent, I act, and I own a public relations company that focuses on social media engagement. It’s all from my network. When you go out and start a business, you can’t just say, “Okay I’m done with Corporate America,” and “Let me do my own thing.” If you don’t build community, if you don’t build a network it's going to be very hard to sustain.
Gabrielle: I realized in New York, there was not a lot to do for Black lesbians and queer folks. We don’t really have dedicated bars and spaces so I started doing events and it took off. I started focusing on my brand, Raw Honey. I opened a co-working space, and I was able to host an NYC Pride event in front of 100,000 people. I hit the ground running with Raw Honey. My events were all women coming to find community and come together with other lesbians and queer folks. I found my purpose in that.
Lisa-Gaye: After being laid off, I wrote out all of my passions and that’s how I came up with [my company] Shakespeare Agency. It was all of the things that I loved to do under one umbrella. The pandemic pulled that out of me. I had a very large social media following, so I pitched to hotels that I would feature them on my blog and social media. This reignited my passion for travel. I took the rest of the year to refocus my brand to focus solely on being a content creator within the travel space.
Gabrielle
xoN: What have you learned about yourself during your time as an entrepreneur?
Randi: [I learned] the importance of my network and community that I created. When I was laid off I was still keeping those relationships with people that I used to work with. So it was easy for me to transition into social media management and I didn’t have to start from scratch.
Gabrielle: The biggest thing I learned about myself was my own personal identity as a Black lesbian and how much I had assimilated into straight and corporate culture and not being myself. Now, I feel comfortable and confident being my authentic self. Now, I'm not sacrificing anything else for my career. I have a full life. I have friends. I have a social life. And when you are happy and have a full quality of life, I feel like [I] can have more longevity in my career.
Lisa-Gaye: [I'm doing] the best that I've ever done. The discipline that I’m building within myself. Nobody is saying, ‘Oh you have to be at work at this time.’ There’s no boss saying, ‘Why are you late?’ But, if I’m laying in bed at 10 a.m. then it's me saying [to myself], 'Okay, Lisa, get up, it's time for you to start working!’ That’s all on me.
xoNecole: What mistakes do you want to help people avoid when leaving Corporate America?
Randi: You have to learn about the highs and lows of entrepreneurship. You have a fast season and a slow season and I started to learn that when you're self-employed the latter season hits hard. Don't get caught up on the lows, just keep going and don't stop. I’m glad I did.
Gabrielle: I think everyone should quit their job and just figure it out for a second. You will discover so much about yourself when you take a second to just focus on you. Your skill set will always be there. You can’t be afraid of what will happen when you bet on yourself.
Lisa-Gaye: When it comes to being an influencer the field is saturated and a lot of people suffer from imposter syndrome. There is nothing wrong with being an imposter but find out how to make it yours, how to make it better. If you go to the store, you see 10 million different brands of bread! But you are choosing the brand that you like because you like that particular flavor.
So be an imposter, but be the best imposter of yourself and add your own flair, your own flavor. Make the better bread. The bread that you want.
Lisa-Gaye Shakespeare
xoNecole: Will you ever return to your 9 to 5?
Randi: I wouldn’t go back to Corporate America. But I don’t mind working under someone. A lot of people try to get into this business saying, “I can't work under anyone.” That’s not necessarily the reason to start a business because you're always going to answer to somebody. Clients, brands, there’s always someone else involved.
Gabrielle: I went back! I really needed a break and I gave myself that. But, I realized I’m a corporate girl, [and] I enjoy the work that I do. I’m good at it and I really missed that side of myself. I have different sides of me and my whole identity is not Raw Honey or my queerness. A big side of me is business and that’s why I love having my career. Now I feel like my best self.
Lisa-Gaye: I really don’t. For right now, I love working for myself. It's gratifying, it's challenging, it's exciting. It’s a big deal for me to say I own my own business. That I am my own boss, and I'm a Black woman doing it.
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Featured image courtesy of Lisa-Gaye Shakespeare
Originally published on February 6, 2023