10 Regrets From My 20s and the Life Lessons They Taught Me

The reflections below were originally written on 5 November 2018, when I was in my 30s, and were first published on another website. They’ve since been removed from there, but I wanted to share them here as an honest reflection of what I thought I regretted in my 20s at that stage of life.

I’ve kept them as they were, as they capture what it feels like to look back on your 20s with more perspective. I’ve also added a short reflection at the end, now I’m in my 40s, to share how I feel about it all today.

10 Regrets From My 20s and the Life Lessons They Taught Me

When I entered adulthood at 18 and even in my early twenties, being in my thirties seemed decades away. It felt so mature and so far in the future.

Now I’m in my thirties, and, honestly, it arrived in a flash!

Life with a husband, work and kids is so busy that time passes quicker than I could ever have imagined.

It’s only at this point in my life, with so many responsibilities, that I realise how much freedom, money and time I had before children. Back then I always thought I was skint and always thought I was busy. Oh, how I now laugh at my pre-kid self!

With children, a mortgage and a husband, life looks very different. There are responsibilities, routines and a need to stay organised.

It’s now that I realise how much more I could have done in my twenties, not just in terms of experiences, but also in building habits that support long-term wellbeing.

This isn’t about regret, really. It’s about reflection. Because when you look back, you start to see how your twenties quietly shape your health, mindset and lifestyle for years to come.

10 regrets from my 20s and what they taught me

Looking back, these aren’t just regrets. They’re lessons I carry with me now.

At the time, I didn’t always realise the impact of my choices, but with more life experience, it’s easier to see how those years shaped my confidence, my health, my finances and my overall wellbeing.

If I could go back, I wouldn’t aim for perfection. I’d just be more aware, more intentional. And that’s really the point of this list.

Here are 10 things I regret from my late teens to early twenties, and what they taught me.

1. Not travelling more

This is probably my biggest regret. I long to travel the world now, but responsibilities mean it has to wait. That freedom I once had is no longer as easy to access.

At the time, I stayed in a job I loved and assumed I’d always be there. I didn’t take risks. I didn’t step away. I didn’t explore.

Now I realise how much those experiences matter.

I worked a job I loved and thought I’d be there forever, so I was too nervous to leave it. Looking back, I wish I’d had the courage to save up, quit and just go travelling.

Travel isn’t just about ticking places off a list, it builds confidence, independence and perspective. It pushes you out of your comfort zone and shows you what you’re capable of.

2. Staying in the wrong relationships

I stayed in relationships that I knew, deep down, weren’t right. We argued often and things didn’t flow, but I stayed anyway.

I wasn’t perfect in those relationships either, and I learned a lot from them, but they showed me what doesn’t work and who I don’t want to be.

But I also gave a lot of time and energy to situations that weren’t adding to my life.

Your emotional wellbeing is heavily influenced by the people closest to you, and when something feels wrong, it usually is. Learning to walk away sooner would have saved a lot of stress and self-doubt.

3. Always seeking love

I spent a lot of time looking for love, even when I didn’t realise I was doing it. Nights out weren’t just about having fun, they came with the hope of meeting someone.

And when I was in a relationship, it often became my focus.

Even when I went out with friends, part of me was always hoping I might meet ‘the one’. Looking back, that meant I wasn’t always fully present, and sometimes I wasn’t the best friend because of it.

Looking back, I wish I’d spent more time simply enjoying friendships and being present. Strong friendships offer support, stability and connection that last far beyond many relationships.

I wish I’d had more confidence to enjoy my own life alongside relationships, rather than letting them take over.

4. Spending unwisely

I always thought I had no money, but the truth is, I often had enough for my situation, I just didn’t manage it well.

I said yes to everything. Nights out, shopping, social plans.

If people were going for drinks after work or planning a night out, I’d always be there. I rarely said no and would never choose a quiet night in!

I didn’t want to miss out, and that fear of missing out led to poor choices. Debt built up and money disappeared quickly.

Most of my money went on things I didn’t need, like clothes, cigarettes and alcohol, and I convinced myself I didn’t earn enough, when really, although I was on a low wage back then, I just wasn’t managing my disposable income well.

Money habits don’t just affect your bank balance, they affect your mental wellbeing too. Feeling out of control financially creates a constant background pressure that’s easy to underestimate.

5. Not saving

Saving simply wasn’t on my radar. I spent what I earned and often more than that, with no plan or safety net.

I would spend every last penny and then some, without really thinking about the future.

Looking back, even small amounts would have made a difference. A simple budget and a small monthly habit could have created something to build on over time.

I also wish I’d started a savings account or even a pension back then, when I had more disposable income and fewer responsibilities.

Saving creates stability. It gives you breathing space and reduces stress in ways you don’t fully appreciate until you need it. It’s not about having loads of money, it’s about having options.

6. Partying too much

I lived for nights out. Clubbing and partying was just a part of the routine and friendship groups I had, and it felt normal at the time.

Some nights went on until 4am, followed by junk food, more alcohol and smoking far more than I should have at afterparties. Some nights, there was no sleep at all. Back then I tended to work six days a week, so it was straight to work after a night out!

It was rarely just one night out each week, it was several.

But those habits take their toll. Sleep suffers, energy drops and your health gets pushed aside without you really noticing.

Looking back, I do sometimes wonder if I caused any lasting damage to my health during those years.

Now I see how important those basics really are. Sleep, nutrition and movement are the foundation of everything, and without them, everything else feels harder.

7. Smoking

I smoked for ten years. It became part of daily life without much thought, and looking back, it’s hard to believe how normal it felt.

Now, I can’t stand it.

I don’t like being around it and hate walking behind people smoking in the street, giving me a mouthful of their secondhand smoke!

It’s one of those habits where the long-term impact is easy to ignore in the moment, but once you step away from it, the difference is clear. Health is something you don’t fully value until you start protecting it.

8. Caring about what other people think

I cared far too much about fitting in. I would adjust my opinions, my behaviour and even small things just to feel accepted.

That lack of confidence held me back more than I realised. Being yourself sounds simple, but it takes time to get there, and even as we get older, it’s still hard to be our true selves around everyone we meet.

Confidence isn’t something you suddenly have, it’s something you build, and once you do, everything feels easier.

9. Not having a hobby

I didn’t have anything that truly lit me up. No hobbies or interests that I pursued consistently, and looking back, I can see how that fed into everything else.

Without something meaningful to focus on, it was easy to fall into habits like partying or spending.

Now I have things I genuinely enjoy, writing, running, yoga and healthy living, and they bring balance. Hobbies give you purpose, structure and a sense of identity outside of work and relationships.

10. Getting random tattoos

I have five ‘proper’ tattoos and a sixth which is only half there.

The sixth was my name in small italic letters on the side of my foot. I let my friend, who wanted to be a tattoo artist, do it when he got his first tattoo kit. We thought it would fade and disappear because of the skin in that area, but we didn’t go low enough.

Now half the tattoo has faded and half is still there, so from a distance it just looks like a patch of black dirt on the side of my foot! Oops!

My other tattoos are all quite different and not really representative of who I am now. I think that’s the challenge with tattoos, even if something feels right at the time, it might not fit who you are ten years later.

Tastes change. You change.

At the time, they felt like a good idea. Now, they don’t really represent who I am, and that’s the point.

You change and grow. What feels right in one phase of life might not feel the same later on, and that’s a reminder that who you are is always evolving.

What your twenties are really for

Looking back now, I don’t think your twenties are about getting everything right.

They’re about learning, trying things, making mistakes and figuring out what works for you and what doesn’t. That process takes time.

Your twenties shape your habits, your mindset and your direction in life, but they don’t define you forever.

Final thoughts

I used to think in terms of regret, but now I see it as learning.

Every choice, even the ones you’d handle differently now, teaches you something. And those lessons matter, they shape how you move forward.

Looking back at your 20s can bring clarity, but the real value is in what you do next. The habits you build now, no matter your age, can still lead to a healthier, happier and more balanced life over time.

A quick reflection now I’m in my 40s

Now I’m in my 40s and republishing this post from 2018, I feel even more strongly that we’re meant to make mistakes when we’re younger. That’s how we learn, grow, and figure out who we do and don’t want to be.

Looking back, there’s even a small part of me that feels a bit envious of how carefree and irresponsible I could be in my late teens and early 20s, before life became more serious with children, commitments and real responsibilities.

And honestly, I’m glad I lived that life when I did.

At the same time, I’m also incredibly happy with how everything has turned out. A wonderful husband, children, a family home and a successful business, it all came from those earlier years, even the messy parts.

Would I change any of it to go back?

Absolutely not.

(And I even treated myself to more tattoos when I turned 40, so maybe I haven’t learned all the lessons after all…!)