There’s a verse in Proverbs that says, “For lack of guidance a nation falls, but victory is won through many advisers.” Sure, the passage is referring to Old Testament-era government leaders, but trying to pursue your calling while balancing all of the responsibilities and challenges of life can feel like you’re facing down a Philistine army. That’s why we took a page out of Solomon’s playbook and asked some successful entrepreneurs, artists and leaders what they wish they knew when they were first starting to chase their dreams. Because there’s another piece of ancient(ish) wisdom that says hindsight is 20/20.
From the practical to the philosophical, here’s what they had to say:
BIANCA JUAREZ OLTHOFF: As a creative (writer, producer and ideator), I wish I would’ve known the value of organization. In my 20s, deadlines and boundaries felt like rules and water on my creative fire. However, Google Calendar, deadlines and completion management software allowed me to be more creative and productive because I had a direction and deadlines to get to my creative destination. As counter-intuitive as it may feel, creating rules gave me more freedom.
ANGELA DAVIS: I wish I would have known that every lesson, every heartache, every heartbreak, every letdown, every setback, wasn’t happening to me, but for me—that every bit of it was preparing me for who He called me to be.
“I wish I would have known that every lesson … every setback wasn’t happening to me, but for me—that every bit of it was preparing me for who God called me to be.”
BOBBY GRUENEWALD: I spent too much time in my 20s being afraid that I would make the wrong career decisions. I over-processed everything. Looking back, I realize I could have saved a lot of mental energy if, instead of fixating on 20 years down the road, I’d been more focused on listening to God’s voice in the moment.
So often, we can think that one misstep will have an eternal trajectory that can never be fixed and we let it paralyze us. The reality is that most of our decisions aren’t irreversible, and God can use even our wrong decisions to create an incredible path forward.
God gives each of us insight, experience and relationships as tools to help us make decisions. If we’re praying about it, seeking wise counsel and feeling a sense of supernatural peace about it, we should be able to step into our decisions with confidence.
BEN WASHER: I wish someone would’ve have told me that the work stays hard. Surprisingly, 10 years later it doesn’t feel like it’s gotten any easier. Which doesn’t mean it’s not ever fun, but as a whole, a career in entertainment always includes difficult elements.
Honestly, this thing that I thought would eventually become nothing but a source of intense joy can actually take energy away from you. No matter what your job is, God didn’t design the universe so that your job would be the ultimate source of satisfaction in your life. And that’s OK. I find more peace and have more fun embracing that my career can’t deliver everything my heart is seeking.
BRYAN PAPÉ: Read, read, read! I wish I would have taken time to read more, from novels to Harvard Business Review to business books. Looking back, I had so much time that could have been spent learning.
ANDY BARRON: Living the life of a freelance creative person sounds pretty dreamy: Use the gifts God has given you, do what you love to do, make your own schedule, stay up late, sleep in.
That’s fine and all, but what you don’t realize is that the other half involves pricing, invoicing, billing, organization, money management, doing your taxes—things that creatives aren’t necessarily the best at.
The advice I wish I knew in my 20s was that the other half of living this life will always be challenging, so begin to learn and get more comfortable with the business side of things now and it will benefit you.
SCOTT HARRISON: I sometimes get asked for startup advice from social entrepreneurs—many in the very early stages of starting charities to solve important problems. One of the most practical pieces of advice I give is simply, “Pick an airline and stick with them.”
For the first five or so years, I always bought the cheapest fare, and wound up with hundreds of thousands of expiring sky miles spread across dozens of airlines.
Sometimes the cheapest ticket would only save charity: water $13, but price was the only criteria that really mattered.
Even though we’ve always raised our staff salaries and overhead funding separately, we take stewardship of those funds seriously.
But as someone who has taken 75 to 100 flights a year for over a decade, I can tell you that status matters and the free upgrades are always priceless.
So IMHO, pick an airline and alliance that works for you and your team members, and feel comfortable paying the minimal extra amount to build status.