How to Become the Person You’ve Always Wanted to Be
- Guest
- Chelsea Handler
- Read time
- ~5 min
- Uploaded
- 4 Aug 2025
- Duration
- 1:18:04
- Views
- 549.8K
KEYPOINTS
- 01
Let yourself want what you want, without apologizing
Mel's main lesson from Chelsea Handler's book I'll Have What She's Having is that most of us see something we'd love, like a first-class seat, a beautiful house or being a good dancer, and immediately decide 'people like me don't get that.' Handler adds a second step: don't just decide you deserve it, also stop apologizing for wanting more. She notes that men rarely apologize for ambition, while women struggle to claim what they want and to talk about what they got.
- 02
Seeing what you don't want can be just as clarifying
Handler, the youngest of six, grew up with money problems: phones were cut off and there was no extra. In a Wall Street Journal op-ed she wrote that the two people in charge of her family were the two she had the least confidence in. Mel points out that most people look around and say 'I want that.' Handler looked at her home and said 'I don't want that.' By six or seven she had pictured a fierce, independent woman who would lead rather than follow.
- 03
You are never too far gone
Whether you're in a marriage, job or city you don't want, or even sick, Handler says you can still take control of your life and stop tying your happiness to other people. 'No one is unrecoverable. You're never cooked.' She adds that you aren't responsible for other people's happiness. She chooses to spread joy on stage, but nobody can require it of her.
- 04
Mel's definition: confidence is the willingness to try
Mel says Handler models confidence as simply being willing to try: wanting something and going after it, having a problem and moving. Proof that you're capable comes from the trying. Handler separates this from banging your head against the same wall. Be willing 'to make a fool out of yourself one time,' because it might work out. She says real confidence took her more than 25 years of stand-up to build.
- 05
Your worst mistake can open a door
Handler's DUI at 21 led to 48 hours in jail and a DUI class where everyone had to tell their story. Terrified of public speaking, she hid at the back for about 12 weeks until the last session, when she told her story and the room laughed. Classmates told her to try stand-up. The next week she waited about 24 hours in line at the Laugh Factory for a three-minute set. She is clear she is not proud of the DUI.
- 06
One failure doesn't decide your future
After bombing her big showcase at the Montreal Comedy Festival, Handler sat in her hotel room wondering if she would have to work in an office. Within about 72 hours she had crushed a set at Luna Park for an NBC executive who hadn't been in Montreal, and she got her first development deal. Her lesson is that you only need one person to say yes, and that 'lightness and darkness follow each other around like partners.'
- 07
Anger is usually hurt in disguise
Handler's brother died when she was nine, and her father 'fell apart at the seams.' Her nine-year-old brain heard her brother's 'I'll be right back' as a lie. She covered the grief with anger, drugs, alcohol and bombast, and she didn't cry about him until she was 40. In therapy she learned that anger is a shield against vulnerability, that resentment usually means you're hurt and never said what you needed, and that annoyance and judgment say more about you than about the other person.
- 08
Growth can feel like losing yourself for a while
Therapy with Dr. Dan Siegel, whom she met when he was a guest on her Netflix talk show, lasted about two years. One lesson was 'you don't have to be everyone's entertainment.' She went quiet at dinner parties, and friends said they wanted the old Chelsea back. For about two years she felt ungrounded and questioned everything: whether she was unlovable or a narcissist, and why she didn't want a husband. She stopped gossiping, lost some friends and gained better ones, and took about six years off stand-up after burning out in her 30s.
EXAMPLES
- 01
The 10-year-old's hard lemonade stand
On Martha's Vineyard, a regular lemonade stand made her about $17 to $20. She fired her sister Shauna for refusing to sell spiked lemonade to adults, knocked on doors asking for 'other 10-year-olds,' and hired a neighbor kid named Nelson as her barback. By week three she had hundreds of dollars and paid Nelson a 1% commission. She then posed as a 15-year-old to run a babysitting business through Edgartown hotels for three years.
- 02
Seat 2C at age 13
Ever since walking through first class at 10 ('This seems like my group'), she had saved her money. At 13, on a family trip to California, she bought her own first-class ticket from a travel agent on her street without telling anyone. She sat in 2C in kitten heels while her older brothers Glenn and Roy sat in coach. When one came up to protest that she should have given the seat to them or their mom, she told him to go back to his section.
- 03
Leaving home with four new tires
Her dad, a used-car dealer, was thrilled to put four new tires on an old Audi Quattro so she could drive to California. Her mom handed over her sister's birth certificate so she could get into bars. She landed with an aunt and uncle in Los Angeles: nine kids, four dogs and a parrot in a two-bedroom house.
- 04
Dinner with Jane Fonda
Fonda emailed asking Handler to come talk about 'a couple things,' that same night. Over dinner she told Handler she had been awful, obnoxious and under a dark cloud at a party at Fonda's house. Having just started therapy, Handler didn't defend herself, thanked her and called it real sisterhood. Fonda told her: 'Go find out what your problem is because your gifts are plentiful... make your environment be a product of you.' Handler borrowed a line from Maria Shriver: make the first time the last time.
OTHER RELEVANT
- 01
Tell a friend the truth when it's inconvenient
Instead of writing someone off or venting about them, offer a clearer picture of who they could be, as Fonda did. Handler now does this for others, more carefully after therapy, knowing not everyone wants her directness.
- 02
When resentment shows up, ask what you never said
After a weekend with people she loves left her resentful, Handler sat with it for three days and realized she had never told them what she needed. Mel takes the same question for herself: did I actually ask?
- 03
Catch judgment and turn it back on yourself
Each time Handler notices herself judging, she asks what she isn't feeling good about in herself. Her goal is to be someone who is judgment-free and just gets a kick out of people.