Helping more people thrive doing what they love or are passionate about means helping more folks learn from those who came before them and so we asked successful entrepreneurs, artists and creatives to tell us what they would do differently, knowing what they know now, if they were starting over.

Alyssa Ann

While my time as a business owner has been short, just a little more than four years, I think one thing I would do differently if I had to start over -maybe just to get where I’m at now a bit faster, would be knowing and doubting a lot less my knowledge and expertise in my field and also charging more money from the start. Most all business owners think they can’t charge because they don’t trust their level of expertise but truly when you start out, you’re charging for time. When you say I can work 20 of the 30 days in a month as a social media manager along with all the research, content planning, posting, engaging, etc for just $500 you will absolutely get burnt out and to be frank no one wants to work like that. What I would have done is worked on building one solid social media marketing package at a better rate, and then increased my client roster from there, versus trying to have a massive roster and a wide range of services that was offered way too cheap. So if any business owners are reading this, PRICE UP! Read more>>

Lisa Kiraly

If I were to start over as an entrepreneur, I don’t believe I would change much about my journey. But if I could tweak one thing, it would be starting sooner. Would it have been a cosmetic teeth whitening business like the one I own today? Possibly not, because it took all my varied experiences to lead me here. My path has been anything but linear, and looking back, it’s clear that every twist and turn was essential. A few years ago, I was diagnosed with ADHD, which provided much-needed clarity about my unique journey. For most of my life, I’ve been drawn to so many different interests at once that I’d often freeze with indecision. Other times, I’d throw myself passionately into a pursuit only to hit an immovable wall. My diagnosis helped me understand why I’ve had such a diverse and eclectic career path—and why I’m grateful for it. Read more>>

Chantell Pfitzer

I love this question because it allows me to share insights that can help others launch or grow their businesses. If I were to start over, here are the key principles I’d follow: 1. Market Validation Is Everything – Test quickly and affordably: Before investing in branding or infrastructure, I’d focus on validating the demand for my idea with simple, low-cost tests. – Start messy, refine later: The Garage Edit began as a project management company with a basic website, no logo, and just a general idea. By putting it out there, I discovered a demand for garage conversions and organization, which shaped the business into what it is today. Read more>>

Imogen Pickton

At the very start of my freelancing journey, I had only just finished my A levels and was completely new to marketing. I undercharged massively at the start because I had no idea how to price my services. There’s no way I’d have been able to scale my business back then with what I was charging. If I was starting again I would research a lot more before creating packages and build the confidence I needed to charge my worth. I would also put myself forward for more opportunities. When I started my business I wasn’t really advocating for myself and putting my name forward for opportunities. This year alone some incredible things have happened because I’ve put myself forward for them so looking back I do wish I’d done that sooner. Read more>>

Nicholas Levitt

If starting over I would do more research on all the regulations involved, both state and federal. Lots of things popped up along the way that I never even thought about. Adding to the start up costs and slowing down the official release date of our first sauces. Read more>>

Prince Miller

If I were to start over as a graphic designer/videographer, the thing I would do differently is use social media as a tool heavily and upload my work every chance I get. In the sports creative business, it’s all about what you know, but most importantly, it’s about who you know. Posting your work on social media helps get your work into the eyes of other creatives with whom you can network and can help create opportunities for you. Read more>>

Lynette Kaiser

If I were starting from scratch in both careers, I would adopt a mindset focused on action rather than perfection. Early on, I found myself preoccupied with the minutiae–obsessing over every small detail. While attention to detail is important, I realize now that it can be a double-edged sword. By concentrating too much on these tiny aspects, I delayed taking significant actions that could have propelled me forward more quickly. Read more>>