Surfacing: From the Depths of Self-Doubt to Winning Big and Living Fearlessly

by Siri Lindley
Surfacing: From the Depths of Self-Doubt to Winning Big and Living Fearlessly cover
Good Books rating 4.0
Technical
  • ID: 1849
  • Added: 2025-10-10
  • Updated: 2025-10-10
  • Reviews: 3
Reviews
play.google.com · Unknown · 2025-10-18
endearing 3.50

The book is a meandering adventure that focuses on spending time with the author, Abbi Jacobson, as she shares her experiences and reflections. While some parts may feel uninteresting or overly casual, the book is largely praised for its wit, honesty, and the personal connections it fosters with readers.

This book is more than just a recount of a cross-country road trip; it's an intimate journey with Abbi Jacobson, filled with her observations, vulnerabilities, and personal growth. Readers appreciate the time spent with Jacobson, finding her voice sharp and witty as she tackles themes of loss, love, and self-discovery. Some parts, like the drawings and casual observations, may not resonate with everyone, but the overall experience is touching and endearing. The book's strength lies in its ability to make readers feel connected to Jacobson, as if they are sharing these moments with a close friend. While not every segment is equally engaging, the raw emotions and honest reflections make it a pleasure to read.

Quick quotes

    This is not just a book about a cross-country road trip. It is also very much the cross-country road trip of books: a meandering adventure in which the main draw is spending time with the person in the driver’s seat

    While asking many questions about adulthood — like what the impact of tucking in her shirt has had on her life — Abbi Jacobson infuses her sharp and witty voice to tell stories about loss, love and finding yourself.

    A sweetly wistful collection ... touching ... Older readers, however, may feel like Gandalf the Grey ... wanders pleasantly along ... Jacobson asks more questions than she answers, which is as it should be.

goodreads.com · Unknown · 2025-10-18
charming 3.50

The book is a delightful collection of essays and drawings that offer a meandering adventure through Jacobson's thoughts and experiences. While some parts may feel trivial, the overall charm and wit make it a enjoyable read.

Abbi Jacobson's book is a charming mix of essays and drawings that take readers on a journey through her cross-country road trip. The book is filled with sharp and witty observations about life, love, and self-discovery. While some sections, like the drawings of everyday items, might feel unnecessary, the majority of the content is engaging and relatable. Jacobson's honest and quirky reflections make it a delightful read. The book successfully creates a personal connection with the reader, making it a memorable experience. However, not every anecdote is equally compelling, but the overall charm and wit of the writing make up for it.

Quick quotes

    This is not just a book about a cross-country road trip. It is also very much the cross-country road trip of books: a meandering adventure in which the main draw is spending time with the person in the driver’s seat.

    While asking many questions about adulthood — like what the impact of tucking in her shirt has had on her life — Abbi Jacobson infuses her sharp and witty voice to tell stories about loss, love and finding yourself.

    Part travelogue, part diary, you come for the delightful observations about road snacks and the life-changing magic of tucking in your shirt, and stay for the endearingly honest, quirky reflections on life, love, art, and work.

ericalippy.com · Unknown · 2020-12-14
brilliant 5.00

The reviewer absolutely loved this book, finding it to be a deeply personal and introspective journey. They appreciated Jacobson's honesty about her experiences as a woman and her awareness of privilege, making it feel like a trip with a close friend.

The reviewer found 'I Might Regret This' to be a heartfelt and engaging memoir. They particularly enjoyed Jacobson's candid discussions about being a woman in a male-dominated industry and her reflections on relationships and self-doubt. The book's blend of humor and introspection made it feel like spending time with a close friend, sharing both silly moments and deep conversations. The reviewer also appreciated Jacobson's acknowledgment of her privilege and the need for broader discussions on inequality.

Quick quotes

    That ultimately I’m admitting that I’m scared of being alone. But aren’t we all? Isn’t that… the main thing? Aren’t we all secretly terrified that we’re not understood, not seen, not loved, not wanted? Okay, great, cleared that up.

    Mediocrity isn’t a part of the successful women’s handbook, but I’m sorry, boys, for you it is. Women have to push harder, jump farther, stay later, think better, shit faster, all while trying their best to maintain whatever society says today their body should look like, how they should parent, what they should wear, when they should find love, what's inappropriate for them to do, say, be, feel, or fuck. The outward pressures are constant, but the inward congestion of doubts and insecurities are sometimes louder — women really can have it all!

    And I’m a white woman in a leadership position — I can only speak from my point of view. The challenges that women of color face in the workforce are even greater, the hurdles even higher, the pay gap even wider. The ingrained, unconscious bias is even stronger against them. It’s overwhelming to think about the amount of restructuring and realigning we have to do, mentally and physically, to create equality, but it starts with acknowledging the difference, the problem, over and over.

Appears in Lists