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 Phillips

I started working for myself when my boyfriend and I spontaneously quit our corporate jobs and moved from New York City to Asheville, North Carolina, in 2017. Up until that point, I’d heard lots of designers talk about “freelancing,” but in my mind “owning a business” meant you had a physical space, employees, high-level clients. It seemed like a totally different, unattainable thing. Read more>>

Chad Woodford

I would pursue my interests and do what I wanted much sooner, taking Joseph Campbell’s advice to follow your bliss. True, they say that you should never make your passion your vocation because then you’ll learn to hate it and it will stop being your passion. But I couldn’t disagree more. Read more>>

Heather Schiefer

If I were to start over with freelancing today there are SO many things I would do differently. I think the biggest ones are building a network and having a financial plan though. Read more>>

Maggie Amos

This is an interesting question, because I didn’t start my photography business all that long ago (I officially started in December of ’22), but I already have things I would go back and do differently. When I first started out, I poured all my time and energy into a website and social media presence for my business. And while those things ARE important and helpful for growing a small business, they’re not the MOST important aspect. This is especially true in an industry like photography. One thing I’ve learned about growing a photography business (and probably most businesses that offer personalized services to clients) is that perhaps the best way to gain business is through ensuring your clients have such a good experience that they want to come back again AND refer you to friends. The majority of my clients are either returning clients or clients who were referred to me by previous clients. I’ve only gotten a couple of clients through social media. Word-of-mouth is so powerful. So if I were to go back and start over today, I would focus more on offering sessions to friends & family, and then working hard to make those sessions something that they love, so that I can build that reputation that gets me clients through word-of-mouth a lot earlier. Then, in my spare time, work on building a website and social media presence that represents that business well. Read more>>

Antione McCoy

Starting off in this industry can be a great experience! If you’re located in or around a hot market that is. This is where the main role of a Mother Agent (or agency) comes into play, acting as the incubator for your career. Read more>>

Ken Hsu

To answer this question, I must first introduce my background. My undergraduate major was Physics, which is not directly related to art and design. However, my true passion lies in painting, and it is this passion that led me to make a major change. Read more>>

Jamaetra Robinson

If I were starting over, I’d do a couple things differently. I would build my target audience before launching so that I’d be able to set up a strong marketing plan. Read more>>

Edith Sanchez

If I knew being a hair stylist was going to turn into my passion I would choose to start my journey sooner rather than later. I’d choose to push through my fear and believe in myself more. Read more>>

Diamond Jackson

If I could turn back the hands of time, I would go to trade school straight out of high school. Instead, I graduated cosmetology school at 23. If I could go back, I would have taken the business just as serious as the craft. Instead of limiting myself, I would invest in a business mentor and continuing education to learn high income producing skills such as hair extensions and hair coloring. I would have worked extremely hard to become a six figure earner within my first two years of business all while keeping my living expenses as low as possible and investing every single penny outside of that into real estate, IRAs and whole life insurance. The cool thing about real estate is the different strategies you can use to obtain even more real estate, which essentially puts you in a different race and tax bracket. Read more>>

Jason Pla Martinez

Looking back on my journey, I realize that one area I wish I had started working on earlier is building a stronger foundation for my brand. While learning and focusing on the technical aspects and product development are essential, I now understand the importance of having a long-term vision. Envisioning where I wanted to take my product in the next 5 years would have been incredibly helpful, as it would have compelled me to chart a clear path for the growth and success of both myself and my brand. By setting a strategic direction early on, I could have avoided some detours and harnessed my efforts more efficiently to achieve my goals. Read more>>