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25 Random Pieces of Advice for Leaders in Their 20s, 30s or 40s

I may or may not have a big birthday this week. Okay…I may.

Believe it or not, turning 50 has not been as traumatic as I thought it might be. Actually, it’s been remarkably satisfying and gratitude-inducing. I have so much for which I’m thankful.

If you’re a younger reader (which most of you are), I have some great news. At 50, I have as much or more energy than I did a decade or two ago, a much better sense of who God created me to be, and I’m surrounded by people I don’t deserve. And I’m honestly more excited by the next 20 years than I’ve ever been about the future.

But maybe the best part of turning 50? You see things you just couldn’t see at 20, 30, or 40. Okay, maybe you can see them. I couldn’t.  At least not as clearly.

In light of that, what follows are life and leadership tips I picked up in my 20s, 30s and 40s that I’m so thankful I did.

How you live your life up to age 50 likely matters more than you think.

advice to people in their 20s, 30s and 40s

How You Live Your 20s, 30s or 40s Matters

I was recently talking to a friend who had turned 50 a couple years ahead of me. He surprised me by saying that your 50s and are largely pre-determined by how well you lived your 30s and 40s.

Live your 30s and 40s well, and your 50s turn out great.

Live them poorly, and all the problems and issues you never resolved when you were younger sabotage your later years, even beyond your 50s.

When he said that, I gulped. Literally.

I’d seen that reality so many times in my life but never connected the dots.

So in an attempt to help you live your 20s, 30s and 40s well, here 25 random pieces of advice I hope can help.

1. Deal with your issues early

You have issues. Everyone does.

As tempting as it is to believe otherwise, it’s not your wife, husband, kids or job who are causing all the pain in your life. You are the common denominator in everything that’s happened to you. So deal with you.

Go see a trained Christian counsellor. Hire a coach. Read some books. Do what it takes to deal with your junk.

2. Invest in coaches and counsellors who make you better

On that note, most people who need counselling say they can’t afford it. It’s like couples who can’t afford a date night but then spend thousands of dollars on divorce later because their relationship fell apart.

If you need counselling to deal with issues, it’s an investment. Ditto with coaches who can bring out the best in you.

It’s not just an investment in you. It’s an investment in everyone you impact.

3. Get off the fence

Indecision plagues too many people.

Make the best decision you can with the information you have, then humbly pursue it with everything you’ve got.

4. Study and practice faithfulness

Faithfulness is rare. Not just in marriage, but also in life.

Culture teaches us to dispose of anything or anyone we don’t like.

So do the opposite.

Learn how to be consistent, loyal, and steadfast, holding to what you know is right even when you feel like doing the opposite.

5. Live like God loves you and everything you read in the Bible is true

Most people wish someone loved them unconditionally. Someone does.

So live like it.

And while you’re at it, live like everything you read in the Bible is true. Doubt your doubts. You won’t regret it.

6. Be generous when you have no money

Don’t fall for the lie that you will be generous one day when you have money. If you’re not generous now, you won’t be generous then.

Practice generosity with every dollar you receive and everything you have. Then if you ever have money or possessions, they won’t own you.

You will have released their grip from your life long ago. And you will look behind you and already see you’ve been able to make more of a difference than you imagined.

7. Choose a few awesome friends and stick with them

Friendships can be confusing in your 20s, 30s and 40s. Friendship circles change when you leave school, get married and even change jobs.

In the midst of all that change, find a few friends and stick with them for life.

Most people can only handle 5 really close relationships in their life. Choose those 5 well and build into those relationships deeply.

8. Cultivate a circle of people around you who make you better

In the last 20 years, I’ve spent a lot of time trying to intentionally pursue friendships and relationships with people who are smarter, more skilled and simply ‘better’ than me.

One of the best ways to become a better person and leader is to spend time with people who are better than you.

9. Get comfortable being around people who are smarter than you

Deal with your insecurities. Get comfortable being around people who are smarter than you.

It will make you better, but it’s also the key to creating an exceptional team.

If you always have to be the smartest person in the room, you’ll eventually end up in a pretty vacuous room.

10. Relentlessly pursue self-awareness

Self-aware people make the best leaders and frankly, are the easiest people to hang out with in life. Chances are your favourite people are people who are deeply self-aware.

But self-awareness doesn’t come naturally. I’m naturally blind to the impact I have on other people around me.  So are you. If you want more on this issue, here are 4 things self-aware leaders know that others don’t.

11. Make peace with your weaknesses

You’ll never be great at everything.

The sooner you get used to that, the better off you’ll be. Eventually you’ll stop trying to cover up and stop feeling so bad about yourself. That’s progress.

12. Pour increasing amounts of energy into your strengths

Once you realize you’re only great at a few things, you’re free to become even greater at them.

Pour your time, energy and resources into what you do very best. That’s the difference between being good at something and being best in the world.

13. Get comfortable with solitude

Solitude is a thoughtful leader’s best friend. It also is a key to self-awareness.

If you really want to grow as a person and as a leader, and grow in your relationship with God, get comfortable with solitude. I wrote more about solitude and how to practice it here.

14. Wrestle down your pride

Pride is ugly. It gets you into trouble again and again.

The only person to whom your pride looks appealing is you. Think about it…you don’t like pride in anyone but yourself.

So pray it out. Beat it out. Do what you need to do to wrestle it down.

15. Fight cynicism

The more you know, the harder it gets to stay hopeful (the Scripture points this out by the way).

Cynics never change the world; they just tell you why the world doesn’t change.

Don’t be one. Check the cynicism that’s growing inside you.

16. Kill selfish ambition

Ambition isn’t bad. In fact, it can change the world.

Selfish ambition is bad. It can destroy the world.

So be ambitious, but be ambitious for the sake of a cause that’s far bigger than you are.

17. Don’t give into stupid temptations that will come your way

You will be tempted to do stupid things. Don’t.

Don’t have an affair, take short cuts or cheat to get ahead.

It’s so not worth it.

18. Find the high road and live on it

The high road is the hard road. But it’s the best road.

People will try to pull you off the high road again and again. Don’t.

Take it. Every time.

19. Don’t wrestle with a pig

Conversely, the low road has virtually no reward.

Years ago someone dropped this gem on me.

Don’t wrestle with a pig. You both get dirty and the pig liked it.

So so true.

19. Work twice as hard on your character as you do on your competency

Competency is not the main key to success. Character is.

Your competency will take you only as far as your character can sustain you.

20. Persevere through the dry seasons

Your time with God will go flat. Sometimes you’ll think what you believe is a farce.

Even marriage, family and friends go through seasons where everything seems boring.

Hang in there. Your emotions eventually catch up with your obedience. So be obedient.

21. Discover what refuels you and do more of it

Some things give you energy in life, some things drain you.

Figure out what refuels you. Then do more of it.

Your choice, over the long run, is self-care or self-medication. Choose self-care.

22. Book appointments with yourself

Your calendar will naturally fill up with urgent things other people believe are important.

And you will watch a decade or more pass by without doing anything really significant.

Book appointments with yourself to do what really matters, whether that’s taking a day off, being with your family, writing an important talk, or taking time to think.

Then when someone asks you if you’re busy, you can truthfully say “I’d love to help, but I have a commitment.”

23. Trust again

Your heart will get mangled and you’ll be tempted to stop trusting people altogether.

Don’t.

Trust again. Hope again. Believe again.

You’ll be so glad you did.

24. Be bold

Be bolder than you think you should be.

Too many dreams die of timidity.

25. Don’t let fear win

Yep…you’re afraid.

Go for it anyway.

Fear gets the best of far too many leaders. Don’t let it get the best of you.

What About You?

There’s a lot more I could have written about, but 25 random piece of advice is enough for now.

You’ve probably got some great advice too. I’d love to hear it. That’s what the comments are for. Scroll down and leave one. 🙂

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  • Nik A

    This is truly a great read.

    I spent most of my life addicted to drugs and other deviant behavior. I found healing in the lord with the help of many other people who were in a similar position and now I am successful in my career as a chef, successful in my marriage and successful as a new father (god willing, this will continue).

    I intend to share this article with the people in the fellowship that I am a member of that helps me keep away from the bad parts of my life that I so long to put behind me. I think a lot of the people I spend time with could benefit from reading this.

    Thank you for taking the time to write this and know that I intend to share it with many people who hopefully will see it as I have.

    • Nik…thanks for sharing your story and THANK YOU for being such an inspiration to others.

  • Jeremy

    Good points. But, if one did everything that the author writes as imperatives, he or she would be perfect. He is asking for moral perfection here, not human faith that perennially fails. Those sorts of demands can lead one to feeling very inferior.

    • Thanks Jeremy. I appreciate your perspective but that’s not the point of the article. I just love getting better, and the process is often called ‘sanctification’ by the ancients. I’m not there yet, but I love growing. That’s the point.

  • Christina

    Very Nice. I just lost my job. This article was very uplifting

  • Mina Paladino

    Thanks for this article. I made some connections while reading it. If #13 was put at #1, then the rest would fall into place, and would be the by-product of a life lived out in relationship with God, and fully dependent on God’s power and leading.

  • Kim Truong

    Love it – #22 is so important. I am glad to say that a few years back I stumbled into a relationship with a mentor (#2) and that helped me with #1. One of my issues was saying yes to everybody but me. My mentor poured #5 into me and #11 & #14 was a result. Now I confidently say, understand and regularly live out the idea that – “I’m the only me there is. I am not supposed to be anyone else. God has a job for me that only I can do, and that job is not dictated by those in the congregation I serve, but it is directed by the Father through his avenues of authority.”

    I thank God for calling you to the ministry of the blog (and the podcast – love it – I have been listening from the start), and I thank you for your humble spirit in the way you present your information and challenges to the way we’ve done things and the need to change. It has helped me in so many ways.

  • Bob Terpstra

    Just turned 30!, so glad I read these when I did! Great insights thanks so much! Just actually got home from a night of dreaming about starting a mens ministry in the form of a biweekly Christian Gentlemens Lounge, were we have Spiritual topics on the menu and a good stout on tap, curious to your thoughts?

    • Happy birthday Bob. As to your ministry idea…we need more creative ideas like that. Love it!

  • Kobie – burstforth

    Great advice!! I turned 30 this year and I approached in as being ‘awesome for 30 years’ instead of dreading getting older. But I realized that Id never want to go back to being in my 20s and I gave my students advice to stop wishing the time over and be present at every season. Like when God called Moses ontop of the Mountain He told him to BE ontop of it and not think of all the ways to get down again! And I take that same advice day after day.

  • Richard Louis

    Love this article. Very helpful insights for a 30yr old! Lots of simple things but the simple things often make the biggest difference.

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  • John Irwin

    Carey,
    I am a newcomer to your blog and website. I have enjoyed several of you articles, some I ‘enjoy’ because they hit me square between the eyes. The Leader Bias one especially and this one. I want to print these out to share with others and in a notebook for myself, is there a way for me to make them more compact, use less paper, smaller type?
    Thanks so much, John

    • John! Welcome. So glad you’re here! Well, to be straight up honest my blog doesn’t print out well. Not sure what it will take to get it there. BUT, I am in the final edits of a new book taking the best conversations from the blog and reformatting/rewriting them to serve as a discussion primer for church teams. Stay tuned!

  • Timeless stuff here.

    • John! Great to hear from you. It’s been a while since our paths crossed. Hope you’re well!

      • i am. i’m meditating on this incredible list today. and sharing it. thanks so much.

        • and because John shared it, I’m now sharing it. Excellent list here Carey – I personally vibed with #19 the most

  • Matt

    I’m so glad you pointed out cynicism. It’s been a struggle of mine recently. So thank you for the advice. It reminds me that God doesn’t want that for our lives. To look down on the world and scoff. But to show the world love and compassion like He graciously showed us:)

    • Thanks Matt. I think cynicism creeps up on all of us. Good for you for seeing it and sending it away. 🙂

  • apollo

    Thanks buddy. Great piece of advice right here!

  • jonperrin

    Exceptional article! Your lead-off statement about reaping in your 50s what you sowed in your 20s, 30s and 40s was haunting, but true. Thanks for this… keep ’em coming! BTW, Happy birthday!

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  • John

    Whew!!! Just turned 49.. glad i got to this in time.. Seriously, great insights. Got a few there i need to work on, but realized that i have sooooo very much to be thankful for.

    • Totally get that John. Way to go. 50’s not so bad….

  • Tom Pelt

    Concerning conflict & No. 19. My dad reminded me… “A dog can whoop a skunk, but is it worth it?” Solid insights. Thanks for your leadership.

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  • I love every single one of these. So insightful. At 39, I am doing my best to live well and to keep learning.

    • Daniel…love this. Thanks! That kind of attitude produces so much traction. And to other readers, If you’re not following Daniel on social media, you’re missing out. 🙂