Learning From The 3 Biggest Regrets Of My 20’s…

Stephen Hussey

I’m not one for endlessly looking back at the past. 

Of the mixed grab-bag of traits I inherited from my Dad, one ability I’m happy to possess is a tendency to quickly move on from what can’t be changed and instinctively look ahead.

I’m much more interested in where I am now, not where I’ve been.  

And yet, I do find it instructive to learn from what I’ve gotten right and wrong over the years. Looking at one’s habits and mistakes from a decade ago gives you perspective on (a) how far you’ve come, and (b) things you might still need to work on. 

Naturally, if pressed, I could unearth hundreds of small missteps along the way. But that’s not interesting. What’s really useful is identifying patternsin your behaviour– those larger flaws that have cost you actual happiness/time/money/love etc.

Here are three that immediately spring to mind: 

1. I wish I had been more assertive about what I want(in work, relationships, restaurants…)

Plenty of times in my twenties I was happy to sit back and let other people take the reins. This can be liberating, but it can also lead you somewhere you don’t want to go. 

To put it more harshly, I would say one of my worst flaws was  to be something of an “avoider”. I don’t like arguments. I don’t particularly enjoy speaking about my feelings. And my response to confrontation is typically to avoid the situation and attempt to resolve it alone with it alone rather than face it head-on.

This has cost me in both work and relationships – when something could have been solved with a difficult conversation ten times quicker, I would often shirk it in favour of long periods of stewing and brooding over how to fix it, instead of just speaking up for what I thought so the other person knew how I felt.

If there are relationships that give you bad feeling, that’s a sign. 

If there’s a work situation that makes you uncomfortable, or you’re subject to a decision that just feels wrong deep in your gut, confront it as soon as you can.

You don’t have to act impulsively – take a moment first to pause and consider if you’re initial reaction is flawed or faulty.

But once a feeling persists, it needs to be addressed or it will come out in ugly ways later mostly in a black pit of anxiety in your stomach that refuses to be squashed down no matter how hard you will it to. 

2. I wish I had not spent so much time being stressed

Deadlines mean stress. Ambition means beating yourself up constantly. Achieving your potential means you need to be perpetually “busy” and miserable.

Those were the lies I told myself throughout my twenties to justify being obsessive about work. 

I would deliberately put off enjoyment out of some idea that this was a necessary sacrifice. If I was too relaxed and enjoying myself, I would imagine my parents and teachers shaming me for being out partying or going on trips when I could be even more productive. 

Although my twenties are filled with plenty of ecstatic highs and a breadth of adventure, I do wish I had allowed myself to make fun more…well, fun. Instead of always feeling like I should be doing something else.

Now, when I work hard, I try to tell myself, “This is something you want to do, so enjoy it.” And when I have fun, I tell myself, “This is meant to be fun, so enjoy it.”

3. I wish I had taken more chances 

Although I braved several fears in my twenties (writing a book/PhD, putting my work out there in public, talking to women), this is something I just wish I had done more of. 

In fact, it’s probably the highest one on my list of things to keep doing throughout my thirties. Most recently I did this by starting a podcast

I’ve found that by taking small risks constantly, you start to learn, (a) there’s not much/nothing to actually lose, once you stop worrying about failure, and (b) the upside is always worth it. 

While I believe one can be smart in taking risks, especially monetary ones (gambling is dumb kids, so is risking health), most things we perceive as scary in terms of rejection are entirely temporary, and tend to leave us better than we were before for the experience. 


The good news is, even with all these regrets my twenties were still a decade I am immensely proud of – full of achievements, friendship and memories I cherish enormously.

If nothing else it shows that you can get a lot wrong and still get a hell of a lot right as well.

So if you’ve never done so, I encourage you to try this “regret test” for your past decade and see what you come up with. Pick the top 3 and let me know what they are in the comments!  

Do the hard part now, and you’ll have much less to regret later on.

9 Texts No Man Can Resist

5 Responses to Learning From The 3 Biggest Regrets Of My 20’s…

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  1. raila says:

    i’m only 14 years old but this actually help me. first i didn’t assertive in something what i do, second i spent my time being stressed thinking about high school, examination also my-ex. and last i didn’t take a lot of chances, and that is one of my biggest
    regret i ever had. but i believe that i can learn from those mistakes!

  2. Katie says:

    I liked the podcast and I’m in my 40’s :) some great useful things, thank you

  3. Mimi says:

    Plenty of times in my twenties I was happy to sit back and let other people take the reins…

    I at almost 40… we let others take the reins. Not only because its easy sometimes we just didn’t know how or where to begin.. And there are many very controlling people who will without a doubt take control of your live without considering your hopes and dreams.

    only thing I regret is not being firmer in wanting a family or children of my own at an earlier age. I was told it wasn’t the right thing to do. No one is or can ever be completely ready… whatever the age.

  4. vera says:

    Rejection is only temporary. Another truth I`m taking home today! Thank you.

  5. Candy says:

    Bravo, Stephen, for the humility. Humility equals progress toward maturity. Transformation begins with being brutally honest with ourselves. We have to know exactly what our issues are before we can work on them.
    I am working on not taking another person’s bad behavior towards me personally. If I am being a decent person and treating this other person with respect, then their bad behavior is a symptom of their issues, not mine. There’s nothing I have done to cause their behavior. And there’s nothing that I can do to change them, or make them change, or make them want to change. The universe is pushing me into some very serious growth right now. I am at a point in my life where I know that I have to love myself, give myself the respect and treat myself with the dignity that I deserve . And that may mean eliminating some people in my life that I love dearly. Thank you for this thought provoking piece.

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