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What I Learned From 10 Years Of Being An Entrepreneur
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.
Did you know that xoNecole has a new podcast? Join founder Necole Kane, and co-hosts Sheriden Chanel and Amer Woods, for conversations over cocktails each and every week by subscribing to xoNecole Happy Hour podcast on Itunes and Spotify.
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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.
This article is sponsored by Hulu.
UnPrisonedhas returned for its highly anticipated second season, delving deeper into the complex dynamics of the Alexander family.
The series premiere comes a year after its debut season garnered rave reviews from fans and critics and earned record-breaking ratings for Hulu's Onyx Collective brand. UnPrisoned's success can be attributed to its raw, relatable themes and comedic appeal.
Inspired by creator Tracy McMillan's life, the show follows Paige (Kerry Washington), a therapist and single mother whose life takes an unexpected turn when her father, Edwin (Delroy Lindo) --who was released from prison-- moves in with her and her teenage son, Finn (Faly Rakotohavana).
Throughout UnPrisoned's first season, viewers witnessed how Edwin's incarceration deeply affected Paige's life and relationships. In the series, Paige unpacks her trauma through interactions with her inner child and her online followers. Meanwhile, Edwin is overcoming specific struggles with his own past that led to his life of crime, including a dysfunctional upbringing and his mother's arrest. As the Alexanders attempt to reconcile, new challenges arise.
This new season promises to further explore their unconventional family dynamic. Here are several compelling reasons why season two of UnPrisoned should be on everyone's watchlist.
The Alexander Family Life Is Still In Shambles
UnPrisoned's second season resumes where the series left off, with Paige grappling with the fallout from her troubled therapy practice and Edwin navigating life independently after moving out. Meanwhile, Finn faces his own challenges. The teenager is battling anxiety and seeking information about his father—a topic Paige avoids discussing.
The Alexander Family Are Attending Therapy To Resolve Their Underlying Issues
Amid the chaos in their lives, the Alexander family decides to mend their bond by confronting their past traumas. They seek professional help and attend therapy sessions with a “family radical healing coach,” played by John Stamos, a new cast member. This collective effort aims to unravel the complexities of their shared history and strengthen their relationships.
The process of unraveling each character's internal conflicts and their potential impact on future relationships may clash with Paige's textbook therapy approach. While Paige is used to being in the therapist's seat in both career and family, this forces her into the unfamiliar role of a patient during therapy sessions. This shift would compel her to look in the mirror and try a radically different approach.
The Alexander Family Learned A Big Lesson During A Therapy Session
In therapy, the Alexanders are tasked with addressing their individual traumas to salvage their remaining relationships. One of the family therapist’s eccentric suggestions was an exercise involving a family wrestling match. During this session, Paige faces tough questions about her refusal to share information about Finn's father.
While it's unclear whether this scene is reality or fantasy, the image of the family duking it out in the ring certainly makes for hilarious yet compelling television.
Paige Tries Dating Again Following Failed Relationships
Amid her life's chaos, Paige decides to step back into the dating field. However, her many attempts have left her with mixed results. The dating apps have turned out to be a fail, and an outing with her ex Mal (Marque Richardson), who is also her father's parole officer, doesn’t go quite as expected after he brings an unexpected guest – his new girlfriend.
The situation takes an awkward turn when Mal's new partner learns why the former couple split, partly due to Paige's self-sabotage.
UnPrisoned Is A Perfect Balance Of Comedy And Drama
As a dramedy, UnPrisoned takes a comedic approach to its heavy subjects. The show takes us on a ride with Paige's dating misadventures and navigating a friendship with her ex.
Other lighthearted moments include Edwin's attempts at CPR based on online videos and, of course, the antics of the Alexander family's unconventional new healing coach.
The second season of UnPrisoned is now available on Hulu.
UnPrisoned | Season 2 Trailer | Hulu
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The Common Denominator Is You. So, Why Do You Keep Choosing The Wrong Men?
Everywhere you go, there you are. It’s one of those popular sayings (kind of like “It is what it is”) that I find myself using a lot, especially when I’m in sessions with my clients. Why? Well, it’s kind of likean article that I once read that pretty much said our culture likes to play the toxic game of blaming other people because it’s an easy way to deflect from personal accountability (check out “What It Actually Means To 'Hold Yourself Accountable'”). So true, so true,
Well, another way of saying “everywhere you go, there you are” is using the math term “common denominator” — and today, what we’re going to attempt to tackle is, why is it that some of us, if we stepped back a moment to take a very real and honest assessment of our dating life, do we always end up with the same kind of guy? One who really isn’t the best for us; sometimes, not even close.
Before getting into some questions that I think can help you get to the answer, let me just say that this is definitely one of the kinds of pieces that may step on at least your pinky toe before it’s all said and done. At the same time, although this might not be the most comfortable of reads, keep in mind what the late poet, singer, and publisher Tuli Kupferberg once said, “When patterns are broken, new worlds emerge.”
And so, if when it comes to the caliber of men you’ve dated, what you’ve been doing is revealing that your pattern is not really working for your ultimate good, spend a bit of time trying to unpack just why that could be the case — why, at the end of the day, you truly are the common denominator in it all.
How Self-Aware Are You?
About five years ago, I penned an article for the site entitled “These Are The Things Self-Aware People Do Daily.” You know, of all of the things to be in this life, prioritizing self-awareness is king because self-aware people do things like hold themselves accountable, know their strengths and weaknesses, identify their triggers, have good boundaries, self-reflect, pay attention to their own “blind spots” — and they can — eh hem — take feedback and constructive criticism pretty well.
That last one? If you’re constantly in a hamster wheel or even a cul-de-sac when it comes to men, be honest with yourself: did your family, friends, hell, even your co-workers warn you about some of the guys you dated, and you found yourself either defending, deflecting or getting offended? Yeah, self-aware people don’t get down like that because they would rather have peace and be wrong than act like they are always right and remain in chaos.
So yeah, if you’re always in some foolishness or even in relationships that are simply a counterproductive waste of time, pondering how self-aware you actually are is a really good place to start. Self-reflect. Know your weaknesses. Listen to what others have to say about your tendencies. All of this can do you a whole lot of good.
How Humble Are You?
Society is a wild place, boy. The reason why I say that is because, while it’s out here acting like humility is a bad thing, Scripture says, “By humility and the fear of the Lord are riches and honor and life.” (Proverbs 22:4) And why is humility such a vital spiritual attribute? Because, when you’re humble — you’re grateful; you’re teachable; you’re open to seeing things outside of your own perspective; you’re compassionate and empathetic; you’re flexible; you’re forgiving, and you’re able to release your ego so that you can accept what you need over what you want.
What you need over what you want. Chile, if that doesn’t keep some people in cyclic stuff, I honestly don’t know what does. There’s a client that I have right now who only contacts me when she’s basically blown up her life because she constantly gets caught up in a man’s looks and bedroom performance. When I tell her that she needs to stop making that #1 and #2 of things to look for in a relationship, she “uh-huh's” me and then does what she wants to do anyway — only for it to end up wreaking all sorts of havoc…again.
It’s another message for another time about how some of us could stand to look within to see if wanting a fine man above all else is more about validating some deep-rooted insecurities that we have about our own looks (ouch). For now, I’ll just say that if your ego is out here telling you that looks and sexual performance should trump things like character and consistency, it is LYING to you. If you chose to heed the humble side of yourself, you would know that.
And this actually brings me to my next question.
How Stuck Are You in Your “Type”?
The reason why I wrote “According To Experts, We All Have A ‘Type’” back in the day is because it’s true — pretty much all of us have a type which is pretty much a preference; there’s absolutely nothing wrong with that either. At the same time, I’m advising, from very up close and personal experience, that it’s a good idea to spend some time pondering “the origin story” of where your type came from.
Me? I’m always gonna be down for a very tall, hella chocolate, basketball (or soccer) build Black man. However, I’m a sexual abuse survivor and my molester looked a lot like that, so during the healing process of what he did to me, I had to factor in his influence. Plus, my first love also fits the physical mold and he definitely had quite an impact on my life. So…see what I mean? My type didn’t just come out of nowhere. Yes, sometimes your type may have some trauma or drama attached to it. And yes, that might be really uncomfortable to think about; still, that doesn’t mean it’s not true.
Now my late fiancé? He was right at about 6’ and, complexion-wise, he was lighter than I am. He treated me better than most of the men of my past, though — and even though he definitely pursued me for a while to get me to consider us beyond being friends, because I took a risk outside of my type, I learned what it was like to be loved in a healthy way. And what that did for me was it taught me to remain open outside of my standard type. I still like a tall-ass Godiva man, chile (and don’t let him have a beard and be in a tailored suit!). I don’t limit myself to that package, though. To do so would be severely limiting — potentially tragic even.
How Healed Are You?
“Healed” is a word that comes up A LOT in the social media space. When it comes to relationships, specifically, it’s important to ask yourself if you are healed from your past because, if you aren’t, you very well could be reliving it over and over…and over again, whether you realize it (or choose to accept it) or not.
Just so that we’re all on the same page, the word “heal” means things like healthy, sound, and whole. Synonyms for the word include improve, restore, mend, soothe, and rehabilitate. Signs that you have healed from past hurts of a relationship (or a series of relationships) include you don’t think of them with anger or bitterness; you can see the silver linings from the experience; you’ve forgiven them for things that they did wrong (or that simply hurt you — and no, that’s not always one and the same), and you don’t pick (or avoid) other people to be in your life solely based on what someone else did to you.
What I mean by that last one is an unhealed woman may say something like, “I don’t want to do [such and such] for a first date. That’s what my ex liked to do.” The new guy isn’t him, so why does he have to be beholden to your past? Or, “I don’t trust men who won’t let me go through their phone. That’s how I found out my ex was cheating.” You know, for all of the women who like to play a non-animated form ofInspector Gadget (the real ones know), they sure don’t want their phones inspected as much as they like to do all of the inspecting. SMDH. Anyway, I don’t go through phones. For what? I don’t pay the bill and I’m not anyone’s parent. And so, your next guy not preferring it either? That doesn’t automatically mean that he’s up to no good — he may just want his boundaries respected. An unhealed person may not accept that. A healed one tends to, though.
And how can being unhealed play a direct role in you choosing the same guys over and over again? It’s weird because, sometimes you will go back to what’s familiar to you — because the new guy is such a risk, you’d prefer to “stick to the devil you know” than take a chance on someone who rolls very differently. It’s a cryptic way of remaining the common denominator in your dating dynamics. Oh, but it happens all of the time, chile.
What Makes a Man WRONG for You? Specifically?
Okay, with a lot of the inner work out of the way, how do you even come to the conclusion that someone (or several people) is wrong for you? Because you know what? Once you’ve done some real healing (and serious maturing), you can oftentimes find yourself accepting the fact that just because someone may not be right for you, that doesn’t automatically or necessarily make them a bad person. No, not at all.
Although the word “wrong” can mean that something or someone isn’t morally right, wrong also means things like erroneous, not suitable or appropriate, not in accordance with certain requirements, or — and please catch it — out of order (which sometimes consists of the right thing happening at the wrong time). So, if it does seem like you keep choosing (because it is always a choice; that is also where accountability comes in) men who aren’t appropriate, aren’t in accordance with your needs or standards, or who aren’t what you need at the time — why is that? Is it rooted in fear? Impatience? Settling? What?
I have had enough clients go through this to know that it’s not good enough to be abstract about someone being “wrong” for you. You need to set aside one weekend, get some wine and a fresh journal, and really get into what wrong looks like. For instance, if you keep lowering your standards (which is the wrong thing to do, by definition), why is that? Because no matter how wrong the guy may ultimately turn out to be, what you have to be willing to accept is — again — you chose him. Why do you choose what’s wrong? Because, more times than not, some red (or at least orange) flags were waving long before the relationship came crashing down; oftentimes, they reveal themselves within the first couple of dates. You just chose to ignore them.
One more.
Do You Know a Good Man When You See One? You Sure?
As we close all of this out, when you get a chance, please check out “Question: Is The Man In Your Life Good 'TO' You? Good 'FOR' You? Or...Both?” Learning the difference between “to” and “for” took my own relational processing to an entirely new and freeing level. And you know what? Back to the healing point, another way to know that you’ve healed is you don’t generalize men. Meaning, that if you’re out here declaring that there aren’t any good ones, that’s not true; you’re just jaded (I mean, it’s the truth), and that head and energy space is affecting your judgment and perspective.
That said, if you’re constantly selecting the wrong men, ask yourself if you even know what a good man looks like (cue India.Arie’s “Good Man”). Again, by definition, good means things like morally excellent, right, kind, friendly, benevolent, educated, financially sound (not rich, stable and responsible…goodness), genuine, reliable, dependable, responsible, attractive, warm, intimate — satisfactory to the purpose (yes, that’s a literal definition).
For a man to be good for you, you need to know what purpose he is to serve at this particular point in your life because if, for example, all men seem to do, in your eyes, is use you for sex, why are you prioritizing sex over an emotional connection if the latter is the purpose that you seek right now? A lot of women can stop being the common denominator when it comes to choosing the wrong man if they 1) become the good that they seek and 2) do not betray the purpose behind why they even desire a relationship in the first place.
____
I know. When things aren’t going your way when it comes to matters of the heart, it can be easy to always say it’s the man’s fault. If there’s a pattern, though, please be a bit more self-reflective than that.
Once you do, you’d be amazed by how much about you shifts — to where the wrong guys can’t even get close to you, in the way that they used to, anymore.
Because you cease to be the “common denominator” you once were.
And how wonderful is that?
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