

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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There is a unique place where PR, technology and digital media overlap and in that place is where I thrive. In 2009, when social media was newly on the rise, I set out on a mission to marry traditional PR with the latest trends in technology. Since then, I've launched a boutique PR and digital marketing agency, Medley Inc. Through my work in the community, I have educated and trained more than 400 hundred girls and budding entrepreneurs in the areas of technology, social media and leadership development. I'm always eager to connect with others! Twitter: @AshleyRSmall.
'He Said, She Said': Love Stories Put To The Test At A Weekend For Love
At the A Weekend For Love retreat, we sat down with four couples to explore their love stories in a playful but revealing way with #HeSaidSheSaid. From first encounters to life-changing moments, we tested their memories to see if their versions of events aligned—because, as they say, every story has three sides: his, hers, and the truth.
Do these couples remember their love stories the same way? Press play to find out.
Episode 1: Indira & Desmond – Love Across the Miles
They say distance makes the heart grow fonder, but for Indira & Desmond, love made it stronger. Every mile apart deepened their bond, reinforcing the unshakable foundation of their relationship. From their first "I love you" to the moment they knew they had found home in each other, their journey is a beautiful testament to the endurance of true love.
Episode 2: Jay & Tia – A Love Story Straight Out of a Rom-Com
If Hollywood is looking for its next Black love story, they need to take notes from Jay & Tia. Their journey—from an awkward first date to navigating careers, parenthood, and personal growth—proves that love is not just about romance but also resilience. Their story is full of laughter, challenges, and, most importantly, a love that stands the test of time.
Episode 3: Larencia & Mykel – Through the Highs and Lows
A date night with police helicopters overhead? Now that’s a story! Larencia & Mykel have faced unexpected surprises, major life changes, and 14 years of choosing each other every single day. But after all this time, do they actually remember things the same way? Their episode is sure to bring some eye-opening revelations and a lot of laughs.
Episode 4: Soy & Osei – A Love Aligned in Purpose
From a chance meeting at the front door to 15 years of unwavering love, faith, and growth, Soy & Osei prove that when two souls are aligned in love and purpose, nothing can shake their foundation. Their journey is a powerful reminder that true love is built on mutual support, shared values, and a deep connection that only strengthens with time.
Each of these couples has a unique and inspiring story to tell, but do their memories match up? Watch #HeSaidSheSaid to find out!
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Are Your Relationships Serving You Or Sinking You? It’s Time To Take Inventory.
Relationships reflect our inner world and what we believe is possible for us. As we navigate our lives, relationships serve as invitations to do inner work with others. When we are unaware of what is happening internally, it can be a recipe for disaster. You are no longer authentic.
Sooner than later, you may feel drained, depleted, and resentful due to unmet needs and boundary violations.
When your needs aren’t met, you will serve someone else's standards while neglecting your own. This is why it is so vital that we take inventory of our relationships and assess if they are relationships that honor our needs, our boundaries, and our truth.
1. You allow yourself to build more intimacy in your relationships.
Intimacy is the heart of a healthy relationship. When we understand our partners, we build intimacy with them. Vulnerability is a conduit for emotional intimacy in safe relationships. Our relationships thrive when we feel emotionally connected and supported by our loved ones.
Nevertheless, a healthy relationship does not mean a perfect relationship, and sometimes we need to assess and address what's working in our relationships and what may need some fine-tuning. When we are open to learning, growing, and developing deeper bonds with our loved ones, we invite them to preserve our relationship through open dialogue centered around honesty, love, respect, and safety.
2. You are choosing yourself and are being honest with yourself.
When you consider spring cleaning your relationships, you offer yourself a token of love. You are communicating that YOU matter, and your feelings, energy, and the overall health of your relationships matter. Spring cleaning your relationships allows you to be there for yourself.
When we choose ourselves, we advocate for ourselves.
So many of us are starting to realize that we have every right to advocate for ourselves, even if the environment we grew up in did not support our emotional or physical well-being.
Now that we can advocate for ourselves as adults, we get to choose our relationships, not from a place of obligation or fear but from a place of reciprocity, love, and respect.
3. It can help you to get clear on things you may have suppressed.
Suppression happens when we actively push uncomfortable thoughts and feelings out of our minds. When something painful happens, and we are left with no resolve, we can suppress how we truly feel as an act of self-preservation for the relationship.
Nevertheless, with honesty also comes vulnerability with yourself. Maybe you have been unhappy in certain relationships for a while, but it was too painful to address, or maybe you have been suppressing how you feel because that is what is expected of you in your relationships.
Although concealing your feelings may protect you from experiencing them, keep in mind that the body stores all of our emotions. There can be serious long-term side effects of emotional suppression, such as physical ailments linked to autoimmune disease.
Our mind, body, and heart are all interconnected, so assessing your relationships through spring cleaning not only improves your overall wellness but can also prevent anxiety, depression, and other chronic illnesses.
4. You can reflect on how you’re showing up in your relationships.
This one is my favorite! Spring cleaning your relationships gives you an opportunity to see yourself more clearly. If you are going through an imaginary checklist of what everyone in your life is doing wrong, you may be a part of the problem. Spring cleaning your relationships is not about what everyone else is doing wrong; it’s about accountability.
Take this time to reflect on how you show up in your relationships.
Are you kind and respectful to your loved ones? Do you honor their boundaries? What can you do to improve? How can you become a better listener? A better communicator?
Use this time to put a flashlight on your heart and take inventory of the places you love people from. Relationships are co-created, meaning both people play a role in the dynamic. Assess your role in your relationships and be the change you want to see.
5. Setting boundaries will reveal the health of your relationships.
Nedra Tawwab, the author of Setting Boundaries, Find Peace: A Guide to Reclaiming Yourself, defines boundaries as a "verbal or an action that you communicate to someone to feel safe, secure, and supported in a relationship." As we are spring-cleaning our relationships, it’s imperative that we check in with our boundaries.
As humans, we are forever evolving, growing, and changing. As we grow, the boundaries that worked for us ten years ago may no longer serve us today. This is why it is important that we communicate our boundaries as they change. People cannot read our minds, and it is unfair to expect them to, no matter how much you think they should just “know” you.
All relationships need boundaries because people need to know how we want to be treated. In healthy relationships, boundaries are honored, and differences are respected. In unhealthy relationships, boundaries are constantly violated and not taken seriously.
When you learn to set healthy boundaries and you start communicating them through your season of spring cleaning, allow your boundaries to reveal the health of your relationships. This may come with a sigh of relief, or this may come with immense grief, but I once heard someone say, “Struggling with the truth is much better than being comforted by a lie.”
Let your relationships reveal themselves to you so you can form healthier bonds, repair broken bonds, or release connections that no longer serve you.
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Originally published on March 24, 2023