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

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

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

I was recently talking to a friend who had turned 50 a couple of years ahead of me. He surprised me by saying that your 50s are largely predetermined 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 26 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 counselor. Hire a coach. Read some books. Do what it takes to deal with your junk. 2. Invest in coaches and counselors who make you better. On that note, most people who need counseling 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 counseling 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 five really close relationships in their life. Choose those five 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 favorite 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 four 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. 20. 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. 21. 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. 22. 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. 23. 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.” 24. 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. 25. Be bold. Be bolder than you think you should be. Too many dreams die of timidity. 26. 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.