Grant Baldwin felt burned out.
He worked as a youth pastor, which felt like a 24/7 profession. He had to attend student events held late into the night, which left him exhausted.
One night, he came home to find his wife crying. She told him that she felt like she had a roommate, rather than a husband, because he was gone so often.
So Grant did something drastic: he quit his job, with negligible savings, when his wife was four to five months pregnant.
(Editor’s Note: WAT?! Who does that?!)
For the following year, he waited tables and worked odd jobs, cobbling together gig-economy money while raising a newborn. During his rare unscheduled moments, he started crafting a new career for himself as a self-employed public speaker.
Today, Grant Baldwin is a speaker, entrepreneur, coach, and author of The Successful Speaker. He’s earned multiple seven-figures in speaking fees and has helped over 2,000 people become professional speakers.
He shares how he made his dream a reality in this episode.
Here are eight nuggets of wisdom for aspiring entrepreneurs and those who want to make a career shift.
#1: Look Behind-the-Scenes Before You Make a Career Transition
The grass is always greener, until it isn’t.
Find successful people who are doing what you want to do, in the way you want to do them, and study them as they do it.
“I think it’s always helpful to look for people who are doing something similar to you and doing it in a way that you want to do it, who are a step or two ahead of that.”
When Grant wanted to become a speaker, he didn’t look to Tony Robbins for inspiration. He looked at someone who was two steps ahead of himself.
Grant shadowed this person at a conference and had dinner with them before they gave their talk. This gave Grant a well-rounded view of what a “day-in-the-life” of a speaker looked like. From this experience, he realized this was a doable, realistic career for him.
#2: Write Your Own Rules and Decide What Game You’re Playing
There are many entrepreneurs who think that they “need” to do X, Y, and Z in their business to be successful.
That’s the business equivalent of keeping up with the Joneses.
Grant doesn’t blindly follow the rules that others define for success:
“You get to make the rules for the game. You get to decide what makes sense for you, and what winning looks like.”
We can relate this to any venture. Maybe you want to buy real estate, but think you need to buy a multifamily that you can househack because that’s what everyone does and says you should do. Blindly following this advice could delay your entry into real estate.
Don’t fall into the trap of playing by other people’s rules. It’s okay if what you want goes against mainstream advice. There’s no better or worse choice. Write your own rules and stick to them.
#3: Quit Your Job If You Don’t Enjoy 80 Percent of What You’re Doing
If you don’t love at least 80 percent of what you spend a good chunk of your waking hours doing, then why do it?
Use this as a litmus test to decide whether you want to stay at your job, or find something else.
When Grant overheard this sentence at a conference, he paused. He had no plan, but this resonated with him. In that moment, he resolved to resign.
He called his wife and told her he was quitting. He knew they would figure it out. He knew he was meant for something bigger. He also knew that staying with the status quo came with a massive opportunity cost.
Grant shares his thought process:
“That’s not a good enough excuse. When I decided I was going to pursue this speaking thing, I felt like I would rather this be a train wreck and know at least I tried, than to get to the end of my life and be like … I could have made that work, but I’ll never know because I didn’t try.”
#4: Find a Bridge Job
There’s no shame in working odd jobs to make ends meet during a career transition.
When Grant quit his job as a youth pastor, his wife was pregnant. They had little savings. He worked a bunch of odd jobs to make the transition as smooth as possible.
“Those jobs were just to really buy me time to figure out what it was that I wanted to do…I look back and those several months of working odd jobs, new baby, financially – it was pretty thin. Figuring out how to become a speaker. That was really, really tough, but at the same time, that was an incredibly pivotal period of life.”
Grant didn’t settle for the status quo. He pushed through his fears and he and his wife figured out how to navigate this new terrain together. Working those odd jobs gave Grant the mental space to think about what his next moves would be.
#5: Work For Free – Only When You Receive Value in Return
There are a lot of creative entrepreneurs who are often told to work for free in exchange for “exposure.”
The popular opinion is: never work for free.
Grant rejects this all-or-nothing approach and says it’s fine to work for free, as long as you receive genuine value in return:
“It’s okay to speak for free, as long as you know why you’re doing it. Don’t just speak for free – don’t just deliver your art for free – out of the goodness of your heart.”
There are valid reasons to work for free, but the value that you receive should be specific, high, and so good that you would have actively sought out the opportunity anyway.
#6: Be Aware of Burn Out – Is This a Sprint, Or a Marathon?
It’s easy to head straight for burn out if you’re caught up in projects and deadlines that create a huge imbalance between your personal and work life.
How do you know when it’s time to quit because your position is unsustainable?
Grant has a great question that you can ask:
“If you’re in the thick of it, and you’re starting to feel some burn out, I would ask: is this a season, or is this the way it is?”
It’s okay to temporarily have a season in which your work/life balance is untenable, as long as that season has an end date. If you don’t see an end date, reconsider your approach.
#7: Stick To Your Boundaries
How can you avoid burning out in the first place?
James Clear, one of our favorite guests on the show, is an expert on building better habits. He says, “The best productivity hack is saying ‘no.'”
Grant reinforces this idea:
“I think I’ve gotten really good at saying ‘no.’ Like, I have no problem saying ‘no.’ As entrepreneurs especially, I think it’s easy to want to chase opportunities and shiny objects, and there’s no shortage of things that we could be doing.”
It can be difficult to hold onto this perspective in the face of FOMO. When you see others in your industry taking advantage of awesome opportunities, how can you fight the temptation to say yes?
Remember that you’re not playing the same game. You’re playing your game, by your rules.
Grant says that sticking to your boundaries inevitably leaves money on the table. It’s more important to run your business and your life in a way that serves you (and your team, if you have one).
#8: Hire an Amazing Team
If you decide to go the entrepreneurial route, know that behind every successful entrepreneur is an amazing team.
There are many tasks that need to be taken care of in a business. Those tasks may not grab your interest or match up with your skills. In those cases, hire it out.
Grant places a high value on his team:
“I can’t do everything on my own and so I want to make sure that we’re building something in a way that is not the Grant show … If the business is just dependent on Grant showing up every day, then we’re doing something wrong.”
You can start small and hire specific contractors for specific tasks; you don’t need to hire part-time or full-time help right away.
Already have a team in place? Take a sabbatical to see how well your systems run without you. Doing so will help you identify points of failure (in what ways were you still needed?) so that you can address them and build a scalable enterprise.
- The E-Myth Revisited, by Michael E. Gerber
- Rework, by Jason Fried and David Heinemeier Hansson
- Bird by Bird, by Anne Lamott
- The Successful Speaker, by Grant Baldwin
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