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How to Pick a Career (That Actually Fits You)

2023-12-01 · Long video (solo, talking head or whiteboard) · Ali, Helen Tupper · recording, 15:01 · watch on YouTube

Topic: Work and career (also: Mindset, motivation and happiness) · mode: List of tips or lessons · tags: Lesson from a book, Feel-Good Productivity thesis, Sponsor segment present

In a voice-over built on clips of his Deep Dive interview with career expert Helen Tupper, Ali gives seven tips for picking a career that fits: reflect instead of running on autopilot, find your values, skip shiny objects, treat strengths as what gives you energy, explore roles by talking to people, make it easy for people to help you, and remember that everyone has confidence gremlins.

What is said

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

00:00:00 — The problem: stuck in jobs that drain you; the interview with Helen Tupper

  • ★★ Ali says there is a way to build a career you find meaningful and fulfilling without upending your life. — 00:00:00
  • ★★ On his podcast Deep Dive, Ali interviewed career expert Helen Tupper, author of The Squiggly Career, a book on breaking free from the corporate ladder and finding new possibilities at work. — 00:00:00 · Deep Dive
  • ★★ Helen Tupper says a squiggly career means not being limited by a ladder or thinking success only means becoming more senior; dropping those constraints is liberating. — 00:00:45

00:01:04 — Unplug autopilot

  • ★★ Helen Tupper says people rarely reflect on what makes them happy and drives them, so they bounce between jobs; reflecting more first leads to better career decisions. — 00:01:15
  • ★★ Ali says school and university leave little room for self-reflection, so people are often stuck with career decisions made as teenagers, before they knew who they are. — 00:01:44
  • ★★★ Ali's first tip for picking a career, unplug autopilot: think about small details by asking yourself whether you enjoy helping people, are motivated by autonomy and freedom, or need a friendly environment. — 00:02:11

00:02:40 — Play the values game

  • ★★★ Ali's second tip, the values game: to find your core needs at work, ask what qualities your perfect team would have, what work fills your perfect day, and what culture you like to work in. — 00:02:40
  • ★★ Ali's own values: he likes working with energising, entrepreneurial people who are also fun and friendly, his ideal day includes learning and teaching, and his company culture should be chill and positive. — 00:03:16
  • ★★ Helen Tupper: To find someone's values, Helen Tupper listens for "sticky words" that other people don't say, rather than ticking values off a list, because those words are more memorable and get used in career decisions. — 00:03:16
  • ★★ Ali suggests playing your values off against each other in pairs, such as curiosity against ambition, to see which comes out on top; a handful of values is enough to show which roles suit you. — 00:04:02

00:04:20 — Sponsor read

00:05:19 — Skip the shiny objects

  • ★★ Helen Tupper says people get very attached to shiny objects such as grades in large organisations, moving from a B level to a C level, or literal ones like cars. — 00:05:19
  • ★★ Helen Tupper once took a job because of the car it came with, and remembers sitting in the car unsure the job was making her happy. — 00:05:19
  • ★★★ Ali's third tip, skip the shiny objects: perks such as a big salary seem like benefits but can distract from a daily working life that is unfulfilling; focusing on your values avoids a shiny-object career. — 00:06:08
  • ★★ Ali calls working out what you want to be known for an important step in choosing a career; it need not be something you are good at yet, and can be a new skill, a reputation or a personal brand. — 00:06:08

00:06:37 — Switch your strengths

  • ★★ Ali's fourth tip, switch your strengths, follows Helen Tupper: strengths are things that energise you and weaknesses are things that grind you down. — 00:06:37 · energisers and drainers

  • ★★★ Helen Tupper defines strengths as the things that give you energy in your work, even if you are not great at them yet: people who think a strength must be something they excel at dismiss their own. — 00:06:59 · energisers and drainers

    “strengths are the things that give us energy”

  • ★★★ In choosing work, Ali says to focus on what you enjoy: data analysis you are good at but find draining counts as a weakness, while talking to people that energises you is a strength even if you are bad at it. — 00:07:53 · energisers and drainers

  • ★★ Ali likes the energy view of strengths because work should be about how the job makes you feel, not just outcomes: doing well at work does not have to be painful. — 00:07:53

00:08:17 — Be career curious

  • ★★★ If you are unhappy in your job, Ali says, a drastic change such as quitting, starting something new or an MBA is sometimes right, but most of the time much smaller changes make you way happier. — 00:08:17
  • ★★★ Helen Tupper advises being proactively curious about your career: start by exploring specific career possibilities, which is not applying for jobs. — 00:08:41
  • ★★ Helen Tupper's obvious move at Microsoft was her manager's job; now that she runs her own company, her sensible move is to stay in it as it grows. — 00:09:02
  • ★★ Helen Tupper says many people assume the obvious career move, such as their manager's job or a promotion, is right for them; it is a good fit only if it fits their values and strengths. — 00:09:32
  • ★★★ To try out a new role, Ali suggests taking something on where you already work, sharing your skills more widely and, most importantly, talking to people who do the job you are interested in. — 00:10:06
  • ★★ Instead of looking straight up the career ladder, Ali suggests looking across at other roles to see what is available. — 00:10:36

00:10:57 — Help people help you

  • ★★ Ali says networking can feel like a club he does not belong to, but most people genuinely want to help and will lend a hand if asked the right way. — 00:11:20
  • ★★★ Helen Tupper: When asking a possible mentor for their time, Helen Tupper says to explain why you are coming to them and what you want to learn, and to ask for half an hour to hear their insights. — 00:11:20
  • ★★ Helen Tupper says asking "will you be my mentor?" asks for a recurring commitment of time; people should make it as easy as possible for others to help them. — 00:12:04
  • ★★ Ali advises always following up with mentors: try what they suggest and report back, because people like to feel their time and advice were worthwhile. — 00:12:33

  • ★★★ Ali's last tip, collective confidence, comes from Helen Tupper's idea that everyone struggles with confidence; she calls these problems confidence gremlins, inner voices that hold us back. — 00:12:33

    “She calls our confidence problems confidence gremlins, the little voices inside our heads which hold us back.”

00:12:45 — Collective confidence

  • ★★★ Helen Tupper says the first step with confidence is knowing you have a confidence gremlin and that everyone else has one too, however senior. — 00:13:14
  • ★★ Helen Tupper: In a recent confidence session with a group of lawyers, Helen Tupper had everyone raise a hand for each of the 10 most common confidence gremlins they identified with, and they realised they all had them. — 00:13:43
  • ★★★ When thinking about your next career move, Ali says to remember that even the most qualified people have doubts and anxieties, and not to let yours hold you back from a job that would make you happier. — 00:14:24

00:14:50 — Sign-off and the full episode

In the description and comments

  • ★ Ali says making this video entirely as a voice-over was a bit of an experiment. — creator comment
  • ★★ Ali Abdaal (channel): Ali's team says it will share the recording of the Feel-Good Productivity annual planning workshop afterwards for those who cannot attend live. — creator comment

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Mentioned

Central: confidence gremlins · energisers and drainers · Helen Tupper

Also: Deep Dive · Microsoft · personal brand · The Squiggly Career

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