The uncertainty of entrepreneurship causes many entrepreneurs to put off starting their business. For others, losing a job or other economic hardships push them starting their businesses earlier than expected. In our conversations with thousands of entrepreneurs we’ve seen so much variety in when, how and why people started their business and so we wanted to share a wide variety of views and reflections on the question of whether these folks wished they had started sooner or waited longer before starting their businesses.

Camryn Mincey

As an entrepreneur I have a drive to achieve. I used to be incredibly hard on myself for not meeting self given timelines. One of my mentors, Jenna Lee, asked me a simple question that helped me refocus. “So? What timeline? Why does that matter?”
All that to say, we can’t control all of life’s twists and turns. Anytime is the perfect time to start a business. It’s never too late and added experience can only be a benefit. Read more>>

Jonathan Sassen

Reflecting on the journey of starting Maverick Seven Group, I recognize the impact of timing and the missed opportunities due to my worries about failure. I launched my flagship business after years of experience in international resorts and nightlife, but fear of failure often held me back from seizing earlier opportunities.

Had I started sooner, I might have taken advantage of favorable market conditions and faced fewer competitors. Many challenges were more daunting in my mind than in reality, and I’ve learned that some ventures succeed while others don’t for various reasons. Read more>>

Sarah Coldwell

I have found myself, at 40 years of age, changing directions. I have put aside my computer screen, stretched my fingers, and plunged them deep into the dirt. I drop tiny seeds into warm soil in May and stand in front a field full of color by July. I wade through flowers up to my armpits by August and am awed by the memory of the tiny seeds I dropped into warm soil just months ago. I am sunburnt, I am tired to the bone, but I am sun-kissed and I find energy in the life and color I bring to the world each summer. Read more>>

Michael Calamaras

Sometimes I wish I had started a business much sooner – ideally while in college. I started smaller businesses after college, and my current endeavor in 2019. When I started my current venture I had been evaluating a shift in various corporate opportunities and business ideas. Read more>>

Lindsey Hebert

I started my online business management company in 2020, but my journey into the world of content creation began a decade ago. My background was in wealth and estate management, a field where I learned the importance of meticulous planning and strategic thinking. However, the birth of my first child in 2020 brought about a profound need for change. I wanted to create a future that allowed for more creativity and flexibility. Read more>>

Sarajo Valenzurla

I wish I would have started my business sooner, I enjoy and love helping people heal and help them move on so that they can put there best foot forward. To give them the tools so that they may break generational curses. My favorite part about what I do, is that at the end of our session I sit my clinet up and we face the wall, I ask them how they are feeling and if they have any questions. At this time if they do I answer them and give any messages that may have came through. Read more>>

Anarsha O’Mealy

As I think back on starting my businesses, of which both started in the same year I would not change much. I believe that everything happens along the timeline of life for a reason and always for the greater good. During the time I started getting into business I was reading a lot of books, becoming more organized and intentional and thinking about ways I could use my gifts and talents to assist the people in my community. I decided to monetize my experience in customer service, cosmetology and decor by creating environments that were aesthetically pleasing, offered high value services and a calming yet welcoming vibe. Leading up to the launch of these businesses I had several experiences that I believe prepared me for that moment. Whether it was providing hair services for my family and friends, decorating a friends space or learning architectural drafting/design; My prior experiences were necessary for the responsibilities I now have in business ownership. Read more>>

Glenda Castro

Everything happens for a reason, there are no coincidences in this life, and I know that the way it was meant for me to start that year (2017), it was perfect timing. I would do it again the same way except that I wouldn’t think about it as much because I was always worried that it wouldn’t be a successful business as it is today. Read more>>

Sammy Fox

Starting my business during the pandemic was either a bold move or a recipe for disaster. Luckily, it was the former. I’m grateful for the challenge, which served as a litmus test for my business model and my sanity. I believe divine guidance from God played a role in my success, but let’s be even more transparent, caffeine and determination were also key players. I wouldn’t change a thing, except maybe the gray hairs I acquired along the way. After a lifetime of hard work, my restaurant is finally up and running, and I’m thrilled with how everything has unfolded. Now, if only I could expand into a bigger space… or a bigger couch for my exhausted self!” Read more>>

Kat Cox

While my business started organically, I wish I had been more serious about it earlier. I started freelance copywriting as a side hustle in the mid-2000s. I wasn’t intentional about it and just accepted work here and there from people who needed help. I always thought of it as something I was doing between jobs or to make money on the side. Read more>>

Summer Mathis

I am firm in …If it happened, it is Right. Sounds simple but it’s how I live. I do not wish I had started earlier or later, she (The Attuned Cauldron) came in precisely when she was needed. I actually had a point when I was given the decision to push and start early and declined. Not letting others around you create your situation can be tough…people can be quite persuasive when they desire something. Short story, I had a girl around me right as I was getting details together for the shop (things like drawing the logo, getting the formulas together for teas, etc.) and this girl was in a bit of a pinch. She wanted to work with me after I opened, but needed a job ‘right now’…basically, she was feeling the pressure of no money..something we all have experienced before. I, on the other hand, was living in a tiny house, not many bills…not concerned about the money aspect as much as I was birthing this baby to last. Completing her one step at a time. I (with my husbands help) had to come to the conclusion that I was not willing to forfeit any part of my ideas for anyone. She moved on to do what was needed in her life and I took my time to create something that would last beyond what I can imagine. Never underestimate old fables…’The Fox and the Crow’ is an excellent piece. The crow was lost in flattery from the fox and forgot her goal. Breakfast. Short story shorter, the fox gets her breakfast because she strayed from her pathway, her goal. Don’t let others move you, You move You. Then you see there is no need for wishing…If it happened, it is Right. Read more>>

Ashley Weber

I started teaching Pilates young, back in 2005 when I was barely 20 and it took me 18 years of being in the career to finally venue forth and create my own Pilates Teacher Training Program and open my own Private Pilates studio: The Pilates Apothecary! I tried my own studio business once before. A few years back before the pandemic, I had a studio in my home for 2 years but it inevitably fizzled out because of the pandemic. My career has had many wins and fails, and I have learned from all of the trials and errors. I feel more emotionally mature now than I have ever been. I’m more grounded and willing to problem-solve than ever before. Also, I trust my gut instinct, am resourceful, and most importantly, I am not shy to ask for help. I believe starting my teacher training: Pilates for the People: rainbow Bridge Program, and my new Studio: The Pilates Apothecary is just the right timing! Past lessons have provided me with the knowledge to create a sustainable business. It is thrilling! Read more>>

Cassie Lopez

Although I learned how to sew and started making custom pieces for friends in my late 20s, Casstastrophe wasn’t really born until 2022.

I was working a dead end job at a car dealership, and I was miserable. I didn’t really know what I wanted to do with my life, but I knew that wasn’t it. It was time for a change. Read more>>

Stacey Benitez

Always sooner. I had been working in bakeries for 14 years before I started “Whisk & Twirl.” It had always been my dream to run my own cake business, but it was a matter of a million questions running through my mind. When is the right time? Am I good enough? Do I have what it takes to make it successful? How will this affect my family? The more questions I had, the more doubt I had, and the more doubt I had, the longer it took to make a decision. Family was the main reason I finally decided to make the jump. It was a time in my life when my only child was entering her teenage years, and I knew I wanted to be there for her as much as possible. Running my own business would allow my schedule to be more flexible, and I could make time to attend her school activities. I knew everything else would be “figureoutable,” and it was! Starting is the hardest part, especially when you don’t know what you’re getting into. It just took baby steps. I created a to-do list, and as I checked things off, the momentum got easier and the confidence got bigger. Three years later, I keep thinking that I could’ve started my business sooner, but I don’t regret when I did. I believe it happened when it needed to. Now knowing that I am successful has taught me not to be afraid of the unknown, and I’m able to give that confidence boost to others wanting to pursue their own entrepreneurial dreams. Read more>>

Baylie Brakebill

I like to believe that everything happens when it’s supposed to, but now that I’ve opened my business I wish I had done it sooner! Initially, I was worried about all the responsibility that comes with owning my own business, but I don’t want to live my life driven by fear, so this has been a valuable lesson for me. Launching my business was overwhelming at the time; however, with the support of my family and friends, we successfully made it happen and the stress was worth it. I am still learning and will continue to gain insights into both the business and technical aspects! Read more>>

Natalia Johnson

If I could go back in time, I wish I had started my travel business way sooner than two years ago!

I launched my business at a pivotal moment—juggling the demands of work, motherhood, a new relationship, and life. I was also finishing my master’s program, buying a home, and moving back to Texas from out of state. It was a whirlwind of responsibilities and changes all happening at once. Starting my business was a way to gain more control my debt, over my extra travel expenses, and it allowed me to earn more income to earn more, save more, & travel more. Starting my travel business gave me so much more freedoms Read more>>

Daniel Weiner

YouShouldTalkTo is a product of Covid and I joke that I was unknowingly building this business my entire life. After Covid hit, the agency I was leading sales for was decimated. After taking some time off, interviewing, and wanting to get out of the rat race, I decided ‘if not now, when?’. Read more>>