Why Does This Keep Happening? A Conversation on Repeating Patterns

When Life Hits Repeat: Recognizing the Lessons in Your Patterns

Dear Friend,

I’ve been thinking a lot about patterns lately—the ones that keep showing up in our lives, even when we think we’ve moved past them. Have you ever noticed that certain situations seem to play on repeat? Maybe it’s the same kind of relationship dynamic, the same struggle at work, or that familiar feeling of not being enough, no matter how much progress you make. It’s frustrating, isn’t it?

But I’ve come to realize something: patterns aren’t punishments. They’re invitations.

Life has this way of circling us back to the same lessons we need to learn, hoping that this time, we’ll catch on. If the same situation keeps showing up in your relationships, career, or sense of self-worth, there’s likely a message beneath the surface waiting to be acknowledged. The question is—are we willing to pay attention?

Recognizing Your Patterns

One of the best ways to start understanding your patterns is to step back and look at them with curiosity rather than frustration. Ask yourself:

• What situations or feelings seem to repeat in my life?

• Do I keep attracting the same types of relationships (romantic, friendships, work dynamics)?

• Are there certain beliefs I hold about myself that keep me stuck?

• Do I react the same way in familiar challenges, even when I know it doesn’t serve me?

For me, one of my pattern used to be people-pleasing. No matter how much I thought I had worked through it, I’d find myself in situations where I was over-giving, over-explaining, and afraid to disappoint. Different faces, different settings—same pattern. It wasn’t until I asked myself, What am I afraid will happen if I stop? that I started uncovering the deeper lesson.

Getting to the Root

Patterns usually stem from something deeper—an old wound, a belief we’ve carried for years, or a lesson we haven’t fully embraced. If you notice a repeating pattern, try asking:

• What fear, belief, or wound is driving this?

• When was the first time I remember feeling this way?

• What am I being invited to heal, shift, or understand?

Sometimes, we need to sit with the discomfort of our patterns long enough to see what they’re teaching us. They show up, not to frustrate us, but to help us grow.

Breaking the Cycle

Once you recognize a pattern, the power shifts back to you. You get to choose a different response. This doesn’t mean the pattern will disappear overnight, but small shifts in awareness lead to big changes over time.

• Interrupt the pattern: The next time you catch yourself in a familiar situation, pause. Ask yourself, What would I do if I truly believed I deserved better?

• Change your response: Even a small shift—saying “no” when you usually say “yes,” speaking up instead of staying silent, or choosing self-worth over self-sacrifice—can start rewriting the script.

• Give yourself grace: Breaking patterns isn’t about being perfect. It’s about awareness, self-compassion, and a willingness to grow at your own pace.

A Loving Reminder

If life keeps handing you the same lesson, don’t get discouraged. The fact that you’re noticing it means you’re already on the path to change. Patterns repeat until we learn from them, and once we do, we open the door to something new—new relationships, new opportunities, new levels of self-love and freedom.

So if you’re in the middle of a repeating cycle right now, take a deep breath. This isn’t happening to you—it’s happening for you. The lesson isn’t here to hurt you; it’s here to set you free.

You’re not alone in this. I see you, I support you, and I believe in your ability to break through.

With love,

Jennifer ❤️❤️