Skip to content

I Tried AI as a Life Coach for 365 Days - Here’s What I Learned

2025-05-31 · Long video (solo, talking head or whiteboard) · Ali · recording, 36:42 · watch on YouTube

Topic: Tools, apps and tech (also: Mindset, motivation and happiness) · mode: Explanation and tutorial · tags: AI, His own products discussed, Sponsor segment present, His own numbers, Lesson from a book, Family

Ali shows how he has used AI tools as a personal life coach for 18 months: treat the AI as a mirror whose answers are useful rather than true, ask it to challenge you and argue the opposite, remember it gives no accountability and is no therapist, and try workflows such as VoicePal frameworks, Readwise's chat with highlights, Alex Hormozi's 90-year-old-self method, persona and podcast prompts, and a ChatGPT memory prompt that, he says, moved him almost to tears.

What is said

The parts of the video and what is said in each (★ — how much it matters to the video).

00:00:00 — Introduction: 18 months of AI as a life coach

  • ★★ For the last 18 months Ali has used various AI tools as a personal life coach; he was sceptical at first, but the results surprised him. — 00:00:00

00:00:29 — Conceptual framework: raw inputs, and what the AI does with them

  • ★★ Ali sees a lot of value in giving an AI life coach more kinds of raw input than typing: voice recordings, photos of handwritten journals, call transcripts and screenshots. — 00:01:28
  • ★★ Feeding the transcript of a coaching call into AI usually gets Ali a lot more value from the coaching session, because he can reflect on it afterwards. — 00:01:28
  • ★★ An AI can ask you clarifying questions, one of a life coach's main uses: coaches tend not to give advice but mirror what you said, reflect it back and ask follow-up questions. — 00:01:57
  • ★★★ To get around AI sycophancy, which he calls glazing, Ali asks the AI to challenge his thinking: for a steel-man counter-argument, the strongest counter-argument, or a scathing critique of what he said. — 00:02:26
  • ★★ Even an experienced human life coach cannot give you the correct explanation of why you procrastinate on something, Ali says; arguably there is no correct answer. (hedged) — 00:02:55

  • ★★★ Expecting truth from an AI's explanations of you is a recipe for disaster, Ali says: they are not necessarily true but can be useful, so treat them as a suggestion or hypothesis, not a commandment. — 00:03:25

    “The goal is useful rather than true.”

  • ★★ Ali says reflecting with AI on arguments with his wife, which he can probe without limit, has genuinely improved his marriage: he sees what went on from another perspective and finds his action points. — 00:04:23 · Izzy Sealey

  • ★★★ Ali runs an AI's recommendation through his own filter of whether he thinks it is a good idea, rather than outsourcing that thinking to the AI. — 00:05:22
  • ★★ AI tools are very good at synthesis, Ali says: feed one thousands of words of your own journaling and ask it what patterns are coming up. — 00:05:22

00:06:00 — BetterHelp sponsor read

  • ★★ Ali has worked with executive or life coaches for about the last five years, with a weekly session. — 00:07:18

00:07:30 — AI as a mirror, the missing accountability, and when to get professional help

  • ★★★ Ali thinks of both a life coach and AI as a life coach as a mirror, not a source of gospel truth or a superintelligence that knows everything about you. — 00:07:48

    “It's simply a mirror that can reflect back the stuff that you give it.”

  • ★★★ The one key thing a coach does that an AI does not, Ali says, is accountability: people tend to care about accountability only to other people, and people they respect. — 00:08:35

  • ★★ Ali thinks a solid half of the value of all the money he has spent on coaching has been a one-on-one accountability mechanism to make him do what he knows he needs to do. — 00:08:35
  • ★★★ AI chatbots are not designed to be therapists, Ali says: he would not use them to diagnose a serious mental health issue or explore childhood trauma, which is for trained professionals. — 00:09:20 · Mental health
  • ★★ Ali's test for what to ask AI: would he take the problem to a smart, well-read acquaintance without qualifications who does not know him well? Not crippling depression or suicidal thoughts. — 00:09:49

00:10:47 — Brainstorming frameworks in VoicePal: the obituary method

  • ★★ Ali recommends the obituary method, a brainstorming framework in VoicePal: following its reflection prompts you write your own obituary, a good way to clarify what you care about and your values. — 00:10:47 · VoicePal
  • ★★ VoicePal, the app Ali's team built, is a ghostwriter in your pocket: it transcribes what you say and asks follow-up questions, and has recently added brainstorming frameworks. — 00:10:47 · VoicePal
  • ★★ Ali has written his own obituary by answering VoicePal's obituary questions and asking the AI to write it from the cleaned-up transcript. — 00:11:50 · VoicePal
  • ★★ Ali uses VoicePal's frameworks extensively on what he wants from his life and business, and finds speaking his thoughts and going back and forth with AI far easier than typing. — 00:12:19 · VoicePal

00:12:31 — Chatting with your highlights in Readwise

  • ★★ Readwise's basic feature, Ali says, takes you through random highlights from your books and sends a daily email of five, a good way to remember what you read. — 00:12:51 · Readwise
  • ★★★ Readwise's chat with your highlights answers a question from the books you have read and highlighted, which Ali finds far more useful and personal than asking a generic chatbot. — 00:13:20 · Readwise
  • ★ Readwise's chat answers Ali's question about his life's direction with wayfinding versus mapping your life, from Designing Your Life. — 00:13:20 · Readwise
  • ★★★ Ali uses AI for the Solomon Method of journaling, which he took from Alex Hormozi: ask the AI to act as your 90-year-old self; he also recommends doing it without AI. — 00:14:18 · Alex Hormozi

00:14:33 — The Solomon Method: the AI as your 90-year-old self

  • ★★ Ali starts the Solomon journaling by giving the AI raw material such as his journal entries, call transcripts and VoicePal entries. — 00:15:02 · VoicePal
  • ★★ Ali calls his AI 90-year-old self's answers useful, not true, after the title of a Derek Sivers book: none of it is necessarily true or necessarily false. — 00:16:31 · Derek Sivers
  • ★★ Questions Ali brings to his CEO coach include how to balance doing what feels good against doing what sells, and the creative against the commercial incentives of his business. — 00:16:31
  • ★★ Ali suggests giving the AI different personas to distort the mirror, such as a drill-sergeant prompt he found on the ChatGPT prompts subreddit. (hedged) — 00:17:00 · ChatGPT

00:17:11 — AI with different personas: the drill sergeant arguing both sides

  • ★★★ Ali says making videos became a chore when he went full-time on YouTube: monetising a hobby shifts it from something you get to do to something you have to do. — 00:18:54
  • ★★★ One of Ali's top tips for using AI in general: get it to argue the exact opposite of what it first says, which avoids it affirming everything you say. — 00:20:41

00:21:04 — The long-form podcast prompt with two guests

  • ★★ Ali's long-form podcast prompt: tell the AI you are the host of a long-form podcast with two named guests, such as Kapil Gupta and Jed McKenna, who answer your questions. — 00:21:04
  • ★ The podcast prompt came about a few weeks before the video, when Ali was reading Kapil Gupta's book Atmamun. — 00:21:04
  • ★★ Ali, married with a child on the way, asks whether following spiritual enlightenment's elimination of attachments would leave him non-attached to his family. — 00:21:04 · Izzy Sealey
  • ★★ In the podcast prompt Ali likes to pit two guests with very different outlooks against each other to see what happens. — 00:22:52
  • ★★ Ali says many people in his audience struggle with wanting financial freedom while having lots to do and wanting a balanced life. — 00:25:22 · work optional
  • ★ You could turn the podcast-prompt conversation into an audio podcast with NotebookLM, Ali says, but he finds reading quicker than listening. — 00:25:51

00:26:13 — Memory-based deep dive on ChatGPT: his hidden narrative

  • ★★ Ali's memory-based workflow does not work on Claude, which has no memory feature, but works nicely on ChatGPT. — 00:26:13 · ChatGPT
  • ★★ Ali's memory-based prompt for ChatGPT, from the ChatGPT prompts subreddit, asks: what is my hidden narrative and subtext, the one thing I never express, the fear I don't admit? — 00:26:13 · ChatGPT
  • ★★ Ali says he definitely feels the sense ChatGPT describes, that if he pauses long enough something unbearable will catch up with him. — 00:27:35 · ChatGPT
  • ★★ Reading ChatGPT's unpacking of his hidden fear, Ali says he feels himself almost tearing up. — 00:28:53 · ChatGPT
  • ★★ Ali asks whether this is why he always feels guilty when he is not working. — 00:29:23
  • ★★ Ali has paid probably around $100,000 to $200,000 to various coaches over the years. (hedged) — 00:31:55
  • ★★★ A single ChatGPT prompt copied from Reddit hit Ali, he says, in a way none of the professional coaches he has paid ever have. — 00:31:55 · ChatGPT
  • ★★ Ali says he often feels lost when he does not have goals to go after. — 00:33:31

In the description and comments

  • ★★ Ali says he is probably never going to make study content again, as it is far outside his life: his last exam was in 2018 and he studies only for general learning. (hedged) — creator comment

Threads in this video

Where the stories that moved here went next

Mentioned

Central: ChatGPT · Readwise · useful, not true · VoicePal

Also: People: Alex Hormozi · Angus (general manager) · Derek Sivers · Eckhart Tolle · Eric Partaker · Izzy Sealey · Jed McKenna · Jim Rohn · Kapil Gupta · Lewis Howes · Zig Ziglar

Works: A New Earth · Atmamun · Designing Your Life · The Greatness Mindset · The Power of Now · Useful Not True

Organizations: Reddit

Concepts: acceptance and commitment therapy · cognitive behavioural therapy · hustle culture · Mental health · Solomon's Paradox · spider diagram · wayfinding · work optional · writing your own obituary

Products: Claude · Gemini · Grain · Grok · Kindle · NotebookLM · Readwise Reader

← Previous: Getting Rich is a Game. Here’s How to Win. · Next → Most people forget 90% of what they read.