Skip to content
How To Let Go of the Timeline for Your Life artwork

How To Let Go of the Timeline for Your Life

On Purpose with Jay Shetty

September 9, 2026

Jay unpacks why it can be so hard to let go of the life you thought you’d have by now.

Speakers Jay Shetty

TopicsMental HealthHealth & FitnessBusiness

Jay Shetty (0:00)

This episode is brought to you by Mazda. Confidence isn't something Mazda finds, it's something they practice. That's the thinking behind every Mazda, with proactive safety features designed to help keep you more aware, more connected and more engaged with the road ahead. It's why Mazda has been named Consumer Reports' Safest New Car Brand and has won more 2026 IIHS Top Safety Pick Plus Awards than any other car brand, as of July 2026 Visit www.iihs.org to learn more. A lot can happen when an accident doesn't. Visit mazdausa.com to learn more. Consumer Reports does not endorse products or services.

This episode is brought to you by Chase Sapphire Reserve. One of the greatest gifts we can give ourselves is the chance to step outside of our routine. Travel is a way of slowing us down and shifting our perspective. And with the Chase Sapphire Reserve card, every journey becomes even more rewarding. Earn four times the points on flights and hotels booked direct. Enjoy access to award-winning airport lounges, three times the points on dining and reserve exclusive tables. Learn more at chase.com/sapphirereserve.

Cards issued by JP Morgan Chase Bank, NA member FDIC, subject to credit approval, terms apply.

Hey, it's Jay. I don't know what your day's been like, but I was just thinking about you for a minute. And I hope you're being a little patient with yourself because you deserve it. And yeah, I'll talk to you soon.

I know many of us had certain expectations for how we thought our life would turn out. And a lot of us get down on ourselves for not reaching certain dreams or milestones by the time we wanted them done. But here's my take. The biggest thing holding you back isn't your past. It's the future you thought you'd have. When you were younger, you probably had a picture in your mind of what your life would look like by now. Maybe you imagined you'd be married, or you'd have children running around your home. Maybe you thought you'd finally have your dream job, own a house, live in a different city, or simply feel like you'd figured everything out. Whether you realized it or not, somewhere along the way, you started writing a blueprint for your future. Then, life happened. Maybe some parts of that blueprint came true, but others didn't. Maybe you found yourself in a career you never expected. Living somewhere you never planned, healing from a relationship you thought would last forever. Or wondering why everyone else seems to be moving through life while you're still standing still.

And without even noticing it, you began comparing the life you're living to the life you thought you'd be living. I don't think we talk enough about how painful that comparison can be. We spend so much time comparing ourselves to other people that we overlook an even more common comparison. The comparison between who we are today and who we expected to be by now. Sometimes the person we're competing with isn't the influencer on Instagram or the co-worker who just got promoted. Sometimes it's the 20-year-old version of ourselves who confidently believed they knew exactly how life was going to unfold.

You're measuring your real life against an imaginary one. And reality almost always loses to that comparison. So today, I want to talk about letting go of the expectation of what you thought your life would be. I think there are five ideas we need to understand if we're ever going to make peace with that. We'll go through each concept and by the end of this episode, I hope you'll have a completely different perspective on how you think about your future. So let's dive in, because holding too tightly to one version of your life can stop you from seeing the beauty, meaning and possibility in the life that's already unfolding right in front of you.

Now, if this is you, don't get down on yourself, because the fascinating part is psychology shows us that our brains are wired to create this exact struggle. Psychologists have actually been studying this for decades. In cognitive behavioral therapy, there's a concept called should statements. These are the invisible rules we create about how life is supposed to unfold. I should be married by now. I should have my career figured out. I should own a house. I shouldn't still be living with roommates. I should be happier than I am. The word should seems harmless, but it quietly turns hopes into obligations and milestones into deadlines. Here's the problem with should. Every time you tell yourself your life should look different, you're arguing with reality. You're taking the life that's actually in front of you and comparing it to a standard that may have been written 10 or 15 years ago by a younger version of yourself. And when reality doesn't match that expectation, your brain doesn't conclude. Maybe the expectation needs updating. It concludes, something must be wrong with me.

25 more minutes of transcript below

Thousands of transcripts fetched by people building searchable podcast archives

Fetch the whole transcript

The demo key returns a sample episode in full, no card needed:

request
curl -H "x-api-key: pt_demo" \
  https://spoken.md/transcripts/1000651996090

Markdown with the speakers named, for your notes, your knowledge base, or anything that makes HTTP calls.

From $0.10 per transcript. No subscription. Credits never expire. Prices exclude VAT, added at checkout for EU customers. Not what you expected? Email us within 14 days with 20 or fewer credits used and we refund the pack in full.

Using your own key:

request
curl -H "x-api-key: YOUR_KEY" \
  https://spoken.md/transcripts/1000788617694