As bosses, we’re experts in our respective niches. We’ve got experience, smarts, and passion by the truckload, and that fuels our drive as creative entrepreneurs. But there comes a time in many boss’ journeys where we wonder: Do I need more training? Specific certification? An advanced degree? Or maybe just a long block of time where I dedicate myself to nothing beyond deepening my knowledge of the craft?

This question particularly nibbles at us self-taught bosses, who may not have formal training in our area of expertise. And our inner critics just love to point that out, don’t they?:

“Who are you to do the thing when you have no real training? It’s going to take you years of school to get where you want to be. Either pony up $15,000 and another two years of your life, or leave this work to the people who know what they’re doing.”

(This is where I pull out my inner baseball bat and show my inner critic what’s what.)

The thing is, objectively looking at our qualifications is a super important part of what we do. Expanding our knowledge can broaden our perspective on how we view our work, help us feel the flow in our careers, and make the service or product we provide a better value to our clients. Getting more training can also be an incredibly effective way of procrastinating—a very expensive, high-level form of hiding and not actually doing the work.

Here’s one big truth you need to hear: Going to school can feel a hell of a lot less intimidating than putting yourself out there as an expert in your field.

So how do you find out if it makes sense to get additional training, or if you’re just punting the “scary here and now” for some other time?

The key is to dig deep and understand your core motivation for getting that degree/certificate/year of Jedi-like training. Thankfully, we’ve got some great tools for discovering our true motivations. Journaling, meditation, therapy, and good old-fashioned talking it out with friends are all helpful for shining a light in the cave.

Here are a few practical questions to ask yourself:

  • Is this a sound investment in my career? How will be my projected income change between now and once I’ve completed the training? How does that number compare to what the training actually costs?
  • If I make a list of my qualifications now, and my future qualification once I complete the training, will the two lists be that different?
  • What will happen to my business while all of this is happening? Am I realistically capable of juggling both without either suffering? Will I have to shelf my business while I’m in school?
  • How will I survive financially while I’m in school? Do I have savings to cover my living expenses, or will I have to go into debt? Will I have to sell my soul to Task Rabbit to make this happen?
  • How will my life change during this training? How will it affect my relationships? Will I have to find cheap, black market daycare for my kids?

Once you invest time in mulling over these questions, you may find that additional training is the best possible thing you can do with your time and money. Or, you may find that it doesn’t make practical sense to pursue more education. Still third, maybe there’s an adjusted way to make the same thing happen without causing your life to go into a Chernobyl-like meltdown.

Part of being a creative entrepreneur is being able to come up with creative solutions on the fly, so remember that there are usually multiple roads on a map. Other options might include part-time programs, night classes, online certificates, and uncertified versions of your training that are just as useful but don’t result in a very expensive framed piece of paper.

Sometimes, though, extra training in your niche is a lifelong dream. In which case, I cautiously say go for it.

If going to herbalist school or spending two years in a creative writing MFA program has been at the top of your wish list since you were 10 years old, then going back to school might be doing a lot more than making you a more effective expert; it could be fueling your creative passion and making you more the you you want to be. Even if it doesn’t pay off in dollar signs in the end, following your dreams can be good for your soul.

Just be aware that fear of doing the thing also loves to hide in big dreams—there’s that damn sneaky inner critic again!—so make sure you’re not trading your very real current goals for something that might make you happier in the long run.

And here’s a little last-minute perspective: Beyond attending an arts-based high school, Beyoncé didn’t have any formal training for singing and songwriting before she launched her career. Just sayin’.


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Stephanie Stiavetti is a classically trained personal chef and cooking teacher. She’s the force behind Fearless Fresh, where she shares friendly­-fierce guidance with inspiration to sharpen your cooking skills. Check out Steph’s free Kitchen Ninja Resource Library, where she shares free training to help you create food that is delicious, gorgeous, and a reflection of your personal style.