Why I Had to Find My “Slightly Gangster” Side

For most of my life, I was the ultimate people-pleaser. Raised in a traditional southern family, I was taught to always respect my elders, be polite, and make everyone else comfortable. It was a great foundation, but it wasn’t setting me up to stand up for myself, especially in business. And while I was over here working to make everyone happy, I found myself in situations where people took advantage of my kindness.

Over time, I learned that it’s okay to assert myself. In fact, sometimes it’s necessary to be a little “gangster” when the situation calls for it. I don’t mean becoming disrespectful, but adopting a mindset where you’re not afraid to say what needs to be said or ask for what you need.

How Being “Slightly Gangster” Helped Me Grow

In 2020, I chose “slightly gangster” as my word of the year. I needed to step into a bolder version of myself to push through some major business goals. Adopting this mindset taught me a few valuable lessons:

1. Assertiveness Leads to Respect

Being a pushover isn’t sustainable. I realized that by softening my stance in business, I was actually preventing myself from making the best decisions. But when I started speaking up, people began to listen. I even had clients tell me they wanted this bolder version of Ashley because they knew I could deliver real results.

2. Setting Boundaries Boosts Your Energy

Being assertive doesn’t just help you reach your goals; it helps you preserve your energy. Rather than feeling exhausted after managing everyone else’s needs, I found myself more energized and capable. Being a little “gangster” means you can create boundaries that allow you to give your best without draining yourself.

3. Confidence in Communication

We all know that person who talks over you, refusing to hear what you have to say. Recently, I had to deal with a dismissive banker while trying to secure a construction loan for my home. It was frustrating, but rather than shrinking back, I decided to hold my ground. And guess what? He stopped talking over me, and I got my message across. Sometimes a direct approach is the only way to get results.

How You Can Embrace Your “Slightly Gangster” Side

To succeed in business, you need a balance of kindness and assertiveness. Here are some ways to find that balance:

1. Define What Assertiveness Means to You

Maybe you’re someone who finds it hard to ask for what you want. Start by taking small steps to assert yourself in situations where you’d usually let things slide. You don’t have to dive in headfirst; just try being a bit clearer with your expectations and see how it feels.

2. Speak Up, Especially When It’s Uncomfortable

If you feel taken for granted, it’s often because you haven’t communicated your needs. Be vocal and honest, especially in professional settings. It doesn’t mean you’re being rude—it means you’re respecting yourself and your time.

3. Establish Boundaries Early On

Boundaries are vital, particularly in client relationships. By setting boundaries early, you save yourself the struggle of having to assert them later when you’re already stretched thin. Embrace that “slightly gangster” side upfront, and people will learn to respect your time and expertise.

The Wins of Being “Slightly Gangster”

Learning to embrace assertiveness has brought some significant wins my way. For one, my communication has improved. By speaking clearly and directly, I’m able to eliminate misunderstandings and create more productive relationships. It’s also empowered me to make decisions more quickly and confidently, freeing me up to focus on what truly matters.

As we move into Q4 and start planning for the year ahead, I’m keeping my “slightly gangster” side alive. October is the perfect time to map out 2025 goals, so when December arrives, I can wrap up the year stress-free. This mindset has already shown me that I’m capable of more than I realized—I just needed a little edge to bring it out.

Takeaways

To all my fellow business owners out there: Don’t be afraid to assert yourself. Being “slightly gangster” doesn’t mean sacrificing your kindness or values. It means having the courage to speak up, make your needs known, and take charge of your business with confidence.