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What to do if you hate your job

2025-03-11 · Long video (solo, talking head or whiteboard) · Ali, Sahil Bloom · recording, 21:27 · watch on YouTube

Topic: Work and career · mode: List of tips or lessons · tags: Lesson from a book, His medical past, Sponsor segment present

Ali says that besides suffering through a job you hate or quitting to start a business there is a third option, and sets out three paths: a short-term path (energy calendar, energising side projects), a long-term path of building career capital (swallow the frog for your boss, become the person who figures it out, broaden your definition of compensation, dive through cracked doors) and an exit path, a side-hustle experiment while keeping the job; clips of Sahil Bloom add his views.

What is said

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

00:00:00 — Two usual answers to hating your job, a third option, and Ali's own story as a doctor

  • ★★ For people who hate their job, Ali says, the internet offers two options: suffer and grin and bear it, or, as online influencers including Ali suggest, start your own business. — 00:00:29
  • ★★★ Ali thinks the entrepreneurship path is good for a lot of people but not for everyone, and offers a third option for people who hate their job. — 00:00:29
  • ★★ Ali used to be a doctor and did not particularly enjoy the job, so he researched how to make it more fun, put those insights into his book Feel-Good Productivity, and eventually built a business that let him quit. — 00:00:58 · Feel-Good Productivity (book)

00:01:27 — Understanding job satisfaction: autonomy, mastery and purpose (Drive) and career capital (So Good They Can't Ignore You)

  • ★★ Daniel Pink (quoted): In his book Drive, Daniel Pink says intrinsic motivation at work comes down to three things: autonomy, the freedom to decide how you do your work; mastery, learning and getting better; and purpose. — 00:01:27 · identified motivation
  • ★★ Cal Newport (quoted): In So Good They Can't Ignore You, Cal Newport dismantles "follow your passion": to get autonomy and mastery in your job, become really good at the thing even if you are not passionate about it. — 00:02:10 · Cal Newport
  • ★★ Cal Newport (quoted): Cal Newport says that by becoming really good at your work you become more valuable and build career capital, which you can cash in for autonomy and flexibility. — 00:02:39 · Cal Newport
  • ★★★ Ali says that if you don't enjoy your job, you are probably missing some elements of autonomy, mastery or purpose. — 00:02:39

00:03:08 — The three paths to job satisfaction and what is within your control

  • ★★★ Ali sets out three parallel paths to improve job satisfaction: a short-term path of tactical adjustments to your daily experience, a long-term path of building career capital to cash in for autonomy and mastery, and an exit path, a thoughtful transition into something new. — 00:03:08
  • ★★ Even in the most constrained job situations, Ali has found, there is usually something, even something small, that you can control or influence. — 00:04:36

00:04:51 — The short-term path: deconstruct your day and create an energy calendar

  • ★★★ Sahil Bloom says "I hate my job" is a blanket statement to deconstruct: you rarely hate all of your job, so break your day down from start to finish and see which parts create energy and which drain it. — 00:05:05
  • ★★★ Ali's first strategy is an energy calendar: at the end of each day colour-code the day's activities green if they created energy, yellow if neutral and red if draining; after a week the trends show which aspects of your job you actually hate. — 00:05:55
  • ★★ To reduce the red in an energy calendar, Ali suggests micro-adjustments: changing where you do certain tasks, using play, power and people from his book Feel-Good Productivity, or telling your manager which part of the job you find draining. — 00:05:55 · Feel-Good Productivity (book), play, power, people
  • ★★ Ali says it is pretty much impossible to make your calendar entirely green: as an entrepreneur who can do what he wants, his own calendar is not entirely green either. — 00:06:24

00:06:53 — Sponsor read for Brilliant

00:08:21 — Energising side projects and job crafting

  • ★★ Ali's second strategy is energising side projects: a friend of his, drained as a junior doctor in the UK, followed her curiosity about the hospital computer systems as a side project and crafted a role of part-time clinical work and part-time digital transformation. — 00:08:21
  • ★★ By treating her interest in digital systems as a side project, Ali's friend found more fulfilment and energy in her job as a doctor and crafted her own role, now doing part-time clinical work and part-time digital transformation work. — 00:08:50
  • ★★★ Citing psychology research on job crafting, Ali says that in many workplaces what you do need not be what is on your job description, and that most of his viewers, likely in white-collar jobs, have reasonable room to craft their own job. — 00:09:19
  • ★ Partway through filming this video, Ali breaks off to go to a Muay Thai class and comes back to continue it. — 00:09:49
  • ★★ Sahil Bloom says his mentor Tim Cook did not start his own business: he rose through the ranks at IBM creating a ton of value, then joined Compaq, where Steve Jobs looked at his résumé and brought him in. — 00:09:49

00:09:50 — The long-term path: become irreplaceable; Sahil Bloom on Tim Cook rising through other people's businesses

  • ★★ Sahil Bloom: At Apple, Sahil Bloom says, Tim Cook created a ton of value for everyone he encountered and kept rising until he became CEO, and is now a billionaire. — 00:10:28 · Apple
  • ★★ Sahil Bloom says some of the richest people in the world, such as Paul Allen, worked their way up through other people's businesses. — 00:10:28
  • ★★★ Sahil Bloom says that for most people the best path to financial wealth is to create so much value at your job that you are irreplaceable and rise up in someone else's business, without needing to be an owner. — 00:10:58
  • ★★★ Ali's long-term path: to build career capital you can cash in for autonomy, mastery, purpose and more interesting work, aim to become absolutely irreplaceable by adding loads of value, then cash that value in over time. — 00:11:27
  • ★★★ Ali's third strategy is to swallow the frog for your boss: identify something your boss hates doing, figure out how to do it and take it off their plate, which immediately creates value for your boss. — 00:11:27

00:11:38 — Swallow the frog for your boss

  • ★★ If you are unsure how to add value, Ali suggests asking your boss which of their least favourite tasks you could take off their plate, what being twice as good at your job would look like, and what would make them delighted to give you a £50,000 raise in six months. — 00:11:56
  • ★★★ Ali says you do not first get the raise and then show more value: you show increased value over a long enough time until you are irreplaceable and have far more leverage for a raise, a promotion or more flexibility. — 00:12:42
  • ★★ To anyone who doubts that adding value first works in their workplace, Ali recommends Cal Newport's So Good They Can't Ignore You, which cites research behind it. — 00:12:42 · Cal Newport

00:13:13 — Become the person who figures it out

  • ★★★ Ali's fourth strategy is to become the person who figures it out: when handed work you have never done, do some research, ask a couple of key questions and get the job done, and you will constantly be given new things. — 00:13:40 · imposter syndrome
  • ★★ In Ali's own team, the people with a reputation for figuring anything out are given far more opportunities beyond their job description, generally the more interesting things the growing business is doing. — 00:13:40
  • ★★ With ChatGPT, Claude and other AI tools it is increasingly possible to figure almost anything out, Ali says; even if you fail, showing your boss how you tried to solve the problem makes them feel you are irreplaceable. — 00:14:34 · ChatGPT
  • ★★★ Ali's fifth strategy is to broaden your definition of compensation: research shows salary is a hygiene factor rather than a motivating factor, so bad pay demotivates but good pay does not motivate. — 00:14:56

00:15:00 — Broaden your definition of compensation

  • ★★★ Sahil Bloom says compensation is not only money: especially early in your career you can be paid in new opportunities, access, travel and networks, and seeing compensation that broadly is a cheat code. — 00:15:25
  • ★★ As you add more and more value at work, Ali hopes you find you no longer hate your job, because you get mastery, getting better and learning new skills, which feeds intrinsic motivation. (hedged) — 00:15:25 · identified motivation
  • ★★ Ali says most workplaces, managers and non-toxic bosses are totally happy to give autonomy to someone who is doing a good job. — 00:16:10
  • ★★ Sahil Bloom says there will be long periods when you create more value than you receive and others when you receive more than you create, and over really long stretches the two balance out. — 00:16:10

00:16:48 — Dive through cracked doors: the TikTok pitch and the plastic surgery charity website

  • ★★★ Ali's sixth strategy is to dive through cracked doors: some of the most transformative career opportunities, which can change the trajectory of your career and help you enjoy your work far more, are often not presented to you on a silver platter. — 00:16:48
  • ★★ Sahil Bloom says opportunities in your career and life present themselves as a tiny crack in a door, and your sole responsibility is to figure out how to throw yourself headfirst through it. — 00:17:17
  • ★★ Sahil Bloom recalls two young men who asked to meet him for coffee in New York on a Tuesday; only later did he learn they had no plans to be there and booked a flight once he said yes, and two years on they work together on things unrelated to TikTok. — 00:17:46 · TikTok
  • ★★ Sahil Bloom says spotting a tiny crack in the door and diving through it is how you unlock nonlinear, asymmetric things in life. — 00:17:46
  • ★★★ As a medical student, Ali heard a surgeon at a conference lunch say their plastic surgery charity's website was not very good; having designed websites for ten years, he offered to help, and the surgeon accepted. — 00:19:01
  • ★★ Ali says most workplaces have more to do than people to do it, and the most interesting opportunities are not advertised as official job descriptions. — 00:19:30

00:20:00 — The exit path: the side-hustle experiment

  • ★★ Diving through a cracked door at work, such as an unexpected problem that needs solving, cements your reputation as someone who figures things out and is irreplaceable, and you end up enjoying the job more, Ali says. — 00:20:00
  • ★★★ For the exit path, Ali's single biggest recommendation is not to quit your job to start a business but to run a side-hustle experiment: start your first two or three businesses on the side of a day job and build your exit plan. — 00:20:00
  • ★★★ Sahil Bloom says not everyone should start a business: entrepreneurship means being willing to chew glass for a long time and crawl through the mud on crappy problems, and its glamour is survivorship bias. — 00:20:29

Threads in this video

Where the stories that moved here went next

Mentioned

Central: autonomy, mastery and purpose · career capital · cracked doors · energy calendar · job crafting · Sahil Bloom · swallow the frog for your boss

Also: People: Cal Newport · Daniel Pink · Paul Allen · Steve Jobs (entrepreneur) · Tim Cook

Works: Drive · Feel-Good Productivity (book) · So Good They Can't Ignore You · The 5 Types of Wealth

Organizations: Apple · Brilliant · Compaq · IBM · TikTok

Concepts: hygiene factor · identified motivation · imposter syndrome · Plastic surgery · play, power, people

Places: New York

Products: ChatGPT · Claude

Also centred on career capital: Follow Your Passion is Terrible Advice. Here’s Why.

Also centred on Sahil Bloom: This Book Changed How I Think about Time

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