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Leaders Reveal What They Wish They Knew at 27

Leaders Reveal What They Wish They Knew at 27

Nobody can deny the cool factor of launching a new project—be it a startup, new ministry or creative project. But cool doesn’t necessarily mean doable. The fact is, only about 50 percent of new businesses make it past their first five years—and the percentages get worse after that. If you’re one of those people who feels God calling you to change the world (and if you’re reading RELEVANT, you probably are), one of the smartest things you can do is learn from the wisdom of those a little further down the road. We asked some of the most creative, innovative and odds-defying people we know, “What do you wish you knew when you were 27?” 

Amena Brown

I wish I had known that becoming a full-time artist meant becoming an entrepreneur. At 27, I quit my cushy, corporate job to perform spoken word full-time. I had one paycheck’s worth of savings and no idea what I was getting into. It took my going broke, moving out of my nice apartment into a rented room, plus working the night shift taking customer service calls to realize that seeing my dream become a reality was going to involve a whole lot more than just quitting my job. 

Caitlin Crosby
Founder and CEO, The Giving Keys

I wish I hadn’t been so hard on myself. I don’t fit the mold, and that’s actually a good thing. The Giving Keys was created out of a place of my not fitting the “business mold.” Even though I’m older than 27 now, I still have to tell myself this as a daily reminder so I don’t beat myself up for enjoying who I was created to be.

Tyler Merrick
Owner, Project7

I wish I had “believed” what I read in passages like Ecclesiastes 5:10-20 (which starts with “Whoever loves money never has enough”). We lift up success in America because of the American Dream. That’s not a bad thing, but if not submitted to Christ, it will poison you. You’ll be a closet “success-aholic,” odorless to the public but privately bankrupting your soul. The amazing thing is that Jesus knew that about each of us, and He still took it all on the Cross. He’s graciously waiting for us to bow our knee and cast our burdens on Him. He’ll let us chase those things and allow them to hurt us to learn a lesson, because the lesson has been the same since the beginning of time. 

Christine Caine
Speaker, author and founder: A21 and Propel

When I was 27, I was full of passion, faith and expectation. The thing I lacked was an understanding that people are people, the challenges are great, the obstacles are huge. God’s timing is not your timing. Everything is going to take longer than you think and cost more than you imagined. God is far more interested in doing a work in you before He does anything through you. Nothing is wasted. He is always preparing you for what He has prepared for you. I wasted many years feeling disappointed, anxious and discouraged. If I could go back, I would tell myself that if God said it, God will do it, and no man on earth or demon in hell can stop it. He who promised is faithful. Trust Him.

Scott Harrison
CEO, charity: water

I wish I knew how important initial investments in CRM and other database management systems were to scaling a business. There was a moment at charity: water where we had close to half a million supporters in spreadsheets!

Ann Voskamp
Speaker, author

The size of your ministry isn’t proof of the success of your ministry. The very Son of God had a ministry to 12. And one of them abandoned Him. Forget the numbers in your work and focus on the net value. The Internet age may try to sell you something different, but don’t ever forget that viral is closely associated with sickness. Ultimately, what seems like futile work that’s taking an eternity today is exactly what may make the most difference in eternity. And whatever you do, make it a regular practice to retreat to the “back side of the wilderness.” Because when you do not need to be seen or heard—you can see and hear in desperately needed ways.

John Sowers
President, The Mentoring Project

Ignore the vox populi—the popular voice. I spent way too much time worrying about what others thought about me. I let the vox populi shape my identity. I see a lot of young people today doing the same thing. Listen: your identity is not defined by what others say or think about you. It’s not defined by your Twitter and Instagram followers. Burn those ideas. Your identity is hidden with Christ in God. Lean on Him—and work to be excellent at whatever He puts in your heart, no matter how outrageous or crazy it feels.

Banning Liebscher
Pastor, Jesus Culture

Get ready to live in over your head all the time. What God has called you to is going to place you in situations where you encounter your weaknesses and get stretched in ways you had not imagined. Don’t be in a hurry. Slow down and allow God to develop a deep trust in Him. The key to living in over your head, called beyond your capacity, is to trust God with all of your heart. Trust is required for long-term health and sustainability in all you are called to.

Jo Saxton
Author, Director: 3DM

Burying the hurts, wounds and scars of your heart and soul does not make them go away. You cannot eat them away, drink them away, ignore them or hide them in your work or in your relationships. Eventually, they re-emerge (often with habits that are harder to heal than the wounds themselves). You also can’t cheat your body out of rest. Learn to nurture healthy rhythms.

Liz Bohannon
Founder, Sseko Designs

Chasing after bright and shiny is fun. But it can also be dangerous and distracting. Putting one foot in front of the other in a way that is scalable, measured, disciplined and sustainable is infinitely more valuable than chasing after a unicorn that may or may not exist.

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