10 Bold and Innovative Success Habits to Level Up Your Career, Issa Rae Style

You want to win in your career? Then it’s time to flip the script and shake the table! Let’s leave the basic stuff behind—because you’re not here to blend in, you’re here to stand out like that one bold color in an otherwise beige meeting room. Here are 10 habits that’ll have your career glowing and growing in ways you didn’t even know were possible.

Kamy Charles

1/29/20253 min read

a large chalkboard with a chalkboard saying,'10 bold habits for your
a large chalkboard with a chalkboard saying,'10 bold habits for your

1. Create Before You Consume

Before you check your inbox, scroll through LinkedIn, or dive into other people’s to-do lists, do something for you. Whether it’s jotting down a big idea or mapping out your vision for the week, give yourself the main character energy.

How to do it: Spend the first 30 minutes of your workday working on YOUR goals, not someone else’s.

2. Build a “Brag Bank”

Stop waiting until annual review time to remember what you’ve done. Document your wins—big, small, and “I made it through that Zoom call without rolling my eyes”—on a regular basis.

How to do it: Keep a running list in your phone or planner of every time you kill it at work. When someone asks, “What have you been working on?” you’ll have receipts.

3. Stay Nosy (a.k.a. Stay Curious)

Don’t just be good at your job—be interested in how the whole game works. You’re not just here to play; you’re here to eventually write the rules.

How to do it: Ask questions in meetings. Read books or listen to podcasts about industries you don’t even work in. Be that person who knows stuff.

4. Outsource Your Weaknesses

Listen, you don’t have to be good at everything. You’re not a Swiss Army knife. Successful people don’t waste time trying to be “well-rounded”—they delegate, collaborate, or automate.

How to do it: If it takes you three hours to format a presentation, let someone who loves that kind of thing handle it. (Or use AI!)

5. Treat Every Email Like a Pitch

Every email you send is a chance to influence someone, build trust, or advocate for your ideas. Stop sending boring, dry emails—make them work for you.

How to do it: Start with a punchy subject line, be clear and concise, and always end with a call to action.

6. Host “Solo CEO” Meetings

Don’t just go with the flow. Sit down with yourself once a week and review your progress, challenges, and next steps—like a boss.

How to do it: Block 30 minutes on your calendar every Friday for a “Solo CEO Meeting” to strategize your career moves like the powerhouse you are.

7. Be a Connector, Not Just a Networker

Networking is cool, but you know what’s cooler? Being the person who connects people. When you help others win, your name will always stay in the room.

How to do it: Next time you hear someone mention a problem, think about who in your network can help. Then make the intro—it’s free, and it makes you unforgettable.

8. Say “No” with Your Chest

Don’t water down your “no” with apologies or excuses. Saying “no” is how you protect your time, energy, and mental health.

How to do it: “No, I can’t take that on right now, but let’s revisit next quarter” works wonders. Be firm, kind, and unbothered.

9. Build Your Own Board of Directors

Who’s advising you? Who’s hyping you up when you’re doubting yourself? Build a personal board of directors with mentors, peers, and people who want to see you win.

How to do it: Identify 3-5 people you trust and admire. Schedule quarterly check-ins with them to get their insights and advice.

10. Start a “Why Not Me?” Mentality

Stop talking yourself out of opportunities. Don’t have all the qualifications for the job? Apply anyway. Scared to speak up in the meeting? Do it anyway.

How to do it: Next time you hear that little voice of doubt, ask yourself, “Why not me?” Then go for it.

Final Thoughts: Stay Bold, Stay You

Success doesn’t come from playing it safe. It comes from showing up, showing out, and knowing that you belong in every room you step into. These habits aren’t just about climbing the ladder—they’re about owning it. So, get out there, and remember: You’re the plot twist they didn’t see coming.