A quick personal note before we start. I missed last week’s update, and I owe you an apology. We were in the middle of a move, and the boxes won.
This week I’m writing from a hotel room while my wife, Danielle, has surgery. She’s in good hands, and we’re trusting God with the outcome. I’d be grateful if you kept her in prayer for a quick recovery over these next several weeks!
Sitting in a waiting room has a way of turning your mind toward endings. This week mine went to how leaders handle them.
I Almost Stayed Too Long
I almost stayed too long in a role I’d poured years into.
I knew it was coming to an end. Someone better was needed to take over, and a little voice told me it was time. It's always hard to leave something that you helped build, so I continued to stay one quarter at a time.
Then a mentor asked me a question over coffee that I can still hear. Did I want to finish this well, or just finish it eventually?
That question rearranged me. I went home and planned my exit on purpose. I named the end, handed it off cleanly, publicly honored everyone who was involved, and walked away while people still wanted me to stay.
How you leave something is part of how you led it.
A Letter Written in Chains
The clearest picture I know of a leader finishing on purpose comes out of a prison cell in Rome.
Paul wrote 2 Timothy near the end of his life, chained in a Roman cell with most of his companions scattered and his execution close. He could have written a defense of his record, but he wrote to Timothy instead, the younger leader he’d spent years preparing, and the whole letter reads like a handoff. Guard what was entrusted to you. Pass it on to reliable people who can teach others. Then, near the close, Paul looks back over his own race.
For I am already being poured out like a drink offering, and the time for my departure is near. I have fought the good fight, I have finished the race, I have kept the faith.
2 Timothy 4:6-7 (NIV)
Read that list again and notice what it never mentions. Paul says nothing about how he started. He had one of the most dramatic beginnings in all of Scripture, knocked flat on the Damascus road by a light so bright it took his sight, and he left it off entirely. The things he chose to count at the end were the fight he stayed in, the race he completed and the faith he was still holding.
Our culture throws its party at the kickoff. We post the launch announcement and the first-day photo, and the finish barely gets watched, though it’s the part that tells the true story.
Excitement and applause will carry you through a launch, but finishing has to run on character long after the excitement has burned off, which is exactly why strong finishes are rare.
A pilot can fly a flawless route and still ruin the whole flight in the last two minutes. Passengers forget three smooth hours at cruising altitude the second the wheels slam the runway too hard, because the hardest stretch of the job comes at the very end, when the crew is tired and the ground is rushing up.
Paul knew he was on final approach. He chose to spend it getting Timothy ready to fly.
The Myth of the Strong Start
There’s a quiet myth in leadership that a strong start protects you. If I began with integrity and wisdom, the thinking goes, I’ll naturally end that way too.
Solomon’s story says otherwise.
He started as the wisest man who ever lived, built the temple, and watched royalty travel across the known world to hear him think out loud. Then Scripture records the turn. As Solomon grew old, his heart was slowly pulled toward other gods, and he didn’t stay fully devoted to the Lord the way his father David had (1 Kings 11:4).
The wisest man alive still didn’t finish well.
A weak finish is the natural current, and nobody floats upstream by accident. A strong start is a gift, but gifts don’t renew themselves, so finishing well comes down to a decision you keep making every ordinary week, long after anyone is watching.
Paul knew how real that was. In the same chapter where he celebrates his finished race, he mentions a man named Demas, a coworker who had stood beside him for years. Demas, Paul writes, loved this world and deserted him (2 Timothy 4:10). Two men ran on the same team, under the same teaching, and only one of them crossed the finish line.
Your past integrity doesn’t put the ending on autopilot, so the final stretch needs guarding harder than the first one ever did. If you’ve been coasting on a strong reputation, name that honestly this week.
You Won’t Always See the Payoff
Sometimes you finish faithfully and still miss the payoff you spent years working toward.
Moses led for forty years toward one destination. At the very end, God brought him up Mount Nebo, let him see the whole land spread out below, and told him he would not cross over into it (Deuteronomy 34:4). He died looking at the thing he’d never enter.
Pay attention to what he did with that news. He didn’t burn anything down on the way out or turn the people against the next leader, and he refused to decide the whole forty years had been pointless just because he wouldn’t personally enjoy the finish. Earlier, knowing this day was coming, he had asked God to appoint someone so the people wouldn’t be left like sheep without a shepherd. God gave him Joshua, and Moses laid his hands on him in front of the whole assembly.
Paul did the same thing from his cell. He would never see what Timothy went on to build, and he poured himself into Timothy anyway.
A leader who needs to personally cash in on every finish will struggle to hand anything off clean. Finishing well sometimes means pouring yourself into something you won’t be around to enjoy, which is exactly the picture Paul used for himself. A drink offering gets poured out completely, and the one pouring never gets it back.
The leaders who finish best spend their last season making themselves beautifully replaceable.
Designing the Handoff Before You Need It
So how do you actually finish a role well instead of accidentally falling out of it? You start planning the ending long before you reach it. These are the steps I’ve walked through myself and coached other leaders through, and they build on each other in order.
1. Name the finish line out loud
An ending stays a vague “someday feeling” until you say it to real people and attach a real date. Paul named his plainly when he wrote that the time for his departure was near, and that honesty gave Timothy room to get ready.
2. Choose and prepare the person who comes next
Hand them the relationships and the knowledge that never made it into a job description. Let them sit in the hard meetings while you’re still in the room to explain what just happened. Don’t hoard your influence out of insecurity.
3. Bless your successor in public
When you endorse the next leader in front of everyone, your people transfer their trust instead of splitting it. Moses did this with Joshua before the entire community, and the handoff held.
4. Walk away cleanly
Leave while the handoff is still warm, and resist the urge to hover or to keep a back channel open with the people you used to lead. Your absence gives the new leader room to become one. God didn’t fail the mission with you, and He won’t fail it without you.
A finish you plan becomes a gift to the people behind you, while a finish you avoid leaves a mess somebody else has to clean up.
Four Questions to Answer Right Now
Answer these about the direction you’re trending rather than the reputation you’ve already banked.
Are you finishing things lately, or mostly starting new ones and leaving the old half-done?
If your current role ended tomorrow, would you leave it better than you found it, with the next person set up to win?
Have you started coasting on past wins anywhere?
Is there a relationship or responsibility you’re quietly letting rot instead of closing it out with honor?
Whichever question stung, that’s your assignment. Start adjusting toward a good finish this week.
Build One Unglamorous Tuesday After Another
A strong finish gets built long before the finish line is in sight. It’s made of ordinary Tuesdays when the excitement is long gone, and nobody’s watching.
String enough of them together and you build stamina, the kind that carries you through the stretch where quitting starts to feel reasonable. Keep it up for years and finishing well becomes the natural result of thousands of days you didn’t give up.
Paul’s finished race was made of decades of ordinary days, most of them unrecorded, spent walking between cities, stitching tents to pay his own way and writing letters to churches that didn’t always listen. Nobody threw a party for any of those days. They added up to a man who could write “I have finished the race” from a cell and mean every word.
A Word for the Weary
Maybe you’re tired right now. Maybe you’re in the unglamorous middle, where the start is a distant memory and the finish line still isn’t in sight. I’m living my own version of that stretch in a hotel room this week.
You’re not finishing in your own strength. A few lines after Paul describes his finished race, he admits that at his first hearing nobody came to his defense. Everyone deserted him. Then he writes this.
But the Lord stood at my side and gave me strength.
2 Timothy 4:17 (NIV)
Paul didn’t finish alone, and you won’t either. God is more committed to your good finish than you are, and He doesn’t quit halfway.
So this week’s assignment is for both of us. Name the ending you’ve been avoiding and start designing the handoff. Identify whose hands you’re preparing to pick up your mantle. Then name one place you’re tired and need encouragement to keep going. I’d genuinely love to hear both, so hit reply and tell me.
And please keep Danielle in your prayers as she recovers. We’re grateful for every one of you running this race alongside us.
Finish well, leader.
— Jared