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Lonnie Webb

  • Recent Work
    • Fifty-Two
    • Flyhomes
    • Redfin San Francisco
    • Allen Stone, 2022
  • Editorial
  • Portrait
  • Spaces
  • Archive
    • Sean Woolsey Studio
    • Tour from Home for Redfin
    • Bobby Berk for Redfin
    • Redfin Los Angeles
  • Contact
  • Journal
Puerto Rico Portrait 1

Portrait in Puerto Rico

August 07, 2020
Puerto Rico Portrait 2

I asked this guy on the beach in Puerto Rico to take his portrait. I was terrified he’d say no and I would feel embarrassed and rejected. I have battled the fear of rejection for a very long time - often it has felt crippling. I can’t explain why I struggle so much with this, but it’s true.

He was kind and very appreciative - he said yes. Every time I see these photos, I’m reminded that what’s on the other side of fear is often worth the uncomfortable feeling of the unknown.

Tags: portrait
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Webb Journal

A place for thoughts, photos and family life.


@kaitlin.e.webb you’re the last to eat, the last to sleep, the first to comfort. Their chef, stylist, doctor, first love, lifeguard, teacher, and their best friend. You’re the Easter bunny, Santa clause, and the tooth fairy. You lost your
Los Angeles photo booth. | Nov. 2022
I’m an early riser, I always have been. One of my favorite things to do is go on walks. Life slows down a little bit and I’m able to see a little clearer. | Feb 2022
A little over a year ago, I spent time with one of my favorite humans. We laughed a lot and I left feeling full of life. Thank you for trusting me and encouraging me always. Love you Al 🧡.