How to Get Your 20s Self-Confidence Back

Jan 27, 2021. 27/365 days of Daily Writing Practice + life lessons journal of sorts. I’m committing to writing ~100-word article daily. Short or long-form. Ugly or brilliant. The objective is to write daily for 15 mins without fail, even when life happens.

Jayme del Rosario
4 min readJan 27, 2021

If you were like me, you’ve had your most daring, risk-taking, audacious years in your 20s. The decade when you were so full of ideals and energy. When potentials were still full.

I’ve probably tried almost everything I thought of doing in my 20s. I started businesses. I wrote freelance even if I didn’t have the credentials for it. I worked abroad. I traveled solo. I shifted careers. I tried different jobs. I went to unknown territories. I attended events, conferences, seminars I know no one in as a no one. I’ve enrolled in classes. I jumped into relationships. I tried different personas from diplomatic to confrontational. I played with fashion from classic to experimental. I dyed my hair in different shocking colors. I talked to strangers a lot. I explored who I can be and who I want to be.

For sure I went to a lot of places I knew nothing about carrying with me just my youth full of confidence — a silent belief in myself that I will be all right, that I will get by.

It was fun and scary but I tried everything, I didn’t bat an eyelash. I just went for it. I was never afraid to fail. I knew it was the time that was okay to try and fail because I was young. I had no responsibilities. I had no one depending on me to be so serious about life. I loved it even if I also struggled a lot in it because of all the uncertainty. Self-sabotage also seems to be what people in 20s are inevitably doing.

And then I hit my 30s and there was a gradual transition to quiet. Probably also because energy started to dwindle but also because I started settling down in things I discovered I wanted in my life.

Through experiencing different work setups, I discovered I don’t like a 9–5 or a boss, or the office politics. After all the parties and socialization, I realized, I love my peace and time alone. After going through crowded, stressful airports, I still love being in one because that means I’m going somewhere new.

After what felt like a whirlwind of a decade, I wanted to slow down for a bit and dive deeper into the things that I wanted to do. And when you’ve been so tunnel-focused on a few things, you stop doing a lot of other things. I unknowingly stopped exploring and discovering. And then one day I just woke up doubting myself if I can still make my big and small dreams happen.

Self-confidence seemed to have left without saying goodbye. Without practice, like a muscle, it slowly atrophied while I take care of the adult life.

So now I find myself listing, gain self-confidence back in my to-do list.

After a journal-long intro to answer the question, how to get your 20s self-confidence back, the colon is here:

  1. Say yes to one thing that gives you the nerves. I keep joining Zoom meetings to relearn how to talk to strangers not in writing. I join online communities. I jump in calls with clients, which I wouldn’t normally prefer. I just want to show myself I can work my way to small wins again.
  2. Write every day in your future self journal: the person I’m becoming is self-confident. Make this a brain tattoo until you start to believe it again.
  3. Dye your hair. Dress up. Get made up. Do the little things that made you feel confident before, even these superficial ones.

The first 3 things, I already did.

Below are the things I plan to do:

4. Travel solo once possible.

5. Say yes to speak to a crowd.

6. Lead a group or a community.

7. Do a podcast.

8. Film yourself and publish on a Youtube channel.

9. Teach a class.

10. Launch a new product.

I guess the answer to this is to just keep throwing yourself in the ocean. Keep putting yourself in a vulnerable spot so you can keep giving yourself a chance to emerge victorious. Keep collecting small wins. And then brave big win moments.

We don’t get confident by accident. We become confident with repeated daily deliberate choices. This daily writing challenge is one of those acts of bravery for me. What’s for you tomorrow?

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Jayme del Rosario

I write about self-development, mindful living, and discovering life’s work. Get my FREE email course on how to discover your life’s work here: eepurl.com/dms4u