18 Comments

You really nailed the rollercoaster of being a writer – those highs and lows, and the whole struggle with self-identity. It's comforting and kinda cool to see someone else put those messy, hard-to-explain feelings into words. Your personal touch makes it super relatable. Keep sharing these gems!

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Mar 23, 2023Liked by Tobi Ogunnaike

I really enjoy reading your writing. You have such a great way with words and really is a delight to read. To me you are writer 😊, keep writing, it is inspiring

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Mar 19, 2023Liked by Tobi Ogunnaike

I enjoy your writing style Tobi. Looking forward to reading more of your work and following your journey.

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Thank you Jonny! I appreciate you saying that. How did you find my writing?

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Mar 28, 2023Liked by Tobi Ogunnaike

Via Michelle Varghoose's excellent recent guest post on Paul Millerd's newsletter. 2 other writers who I really rate.

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Ah awesome, yeah I enjoy reading their work too. Welcome aboard 😬

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Mar 4, 2023Liked by Tobi Ogunnaike

Yes yes YESS!!! This is amazing tobi. Connected with what you described on so many different levels. This line reallllly resonates with my experience lately: “I have this beautiful affliction where words, ideas and thoughts visit me unannounced and demand that I stop whatever I’m doing to attend to them.” Since I’m just starting to write more regularly and publicly, I lose sight of the fact that the struggles I’m experiencing may just be a natural part of the writing experience and not because there’s something wrong with me. Thank you for sharing your experience and helping me see I’m not alone. So comforting 🙏

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I’m glad this resonated with you! Yeah I feel like even experienced writers struggle with the writer label. Have you thought about writing about those struggles?

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Thank you for writing this, Tobi. I can relate to so much of what you've written here, from our schooling, to that one probing question (i get it more for being a musician than a writer, as people are now accepting writing more as a career path than music). May the universe guide you with every word that you write and let you shine over the entire Substack readership and beyond. You have a wonderful way with words!

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Thank you Jo for the very kind words. It's honestly so rewarding to hear that this resonated with you so much. It's crazy how we often connect most with people when we write the most personal things. If you don't mind me asking, how do you respond when you get that probing question haha

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Not always that well, to be honest! I often remain silent in the hope that they will realise that the new world we are living in is now more in favour of the arts as viable jobs and career paths!

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Thank you for this. I’m also planning to take a break to pursue the pathless path- building a career built of joy rather than what looks good aka the corporate. Reading your work is so inspirational and helps me not feel alone in this journey. I’m also a writer, and I feel like you captured the feeling of the challenges and joys of a writer perfectly. Not sure if you’ve read big magic by Elizabeth Gilbert, but your essay reminds me of her book. Looking forward to reading more of your writing!

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Thank YOU for this heartfelt response. I truly mean that. Congrats on making the decision to leave. I know it's not easy. Even when you've made the decision, it's still tricky to kick the tyres into motion. I wish you the best!

I haven't read that book, but I remember watching a YouTube video a long time ago where she described her fears and anxieties being a writer. It's possible she was referencing this book. I'll check it out.

Do you know what you'll do on your break?

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You are (also) a writer. Among other things. Whatever that means in terms of respective expectations. And I’m happy to be with you on this path. I wish you energy and success.

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Thank you Livio! I love this framing and I will carry it onwards. I wish you the same!

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Tobi! You're story is inspiring and I had so much fun reading your writing. The questions you pose to yourself in writing have me wanting to highlight them all to spend time answering myself. Add me to the list of pathless path folks untangled from the golden handcuff arena hoping you continue to share.

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Thanks Tobi!! Appreciate the heartful response. I'm super inspired by Daniel's Small Bets stuff, so my plan is to launch some small bets (including a coaching biz), travel, and spend more time on creative writing. I'm trying to balance having some structure but also not, since I'm someone who needs some sort of structure to not totally freak out hah. Any upcoming travel plans for ya? Also, if you're interested, would love to chat more about your journey in a 1:1! But also totally understand if you're busy.

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that sounds cool! I've thought about coaching too. I will probably explore that at some point. Yeah I will be travelling soon. Would love to chat! Can you book sometime here? https://calendly.com/tobi-og/30min

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