When times are good it’s easy to feel like entrepreneurship is the only path for you, but what about the times when your hit with multiple crises at once? We wondered if all entrepreneurs have moments when they wonder whether they should have gone with (or stuck to) a more standard job where they worked for someone else.

Nick Fantasia

The quick answer to am I happy is yes, but that would be boring and misleading. No one is happy all the time. That would be an unrealistic expectation. I love what I do. Whether that’s photographing a couples wedding for memories that will last a lifetime, or taking commercial photos for a business to help them grow. My job is about making the clients that hire me happy, which in turn makes me happy. Read more>>

Liz Baynard

I took a leap of faith when leaving a challenging albeit rewarding position as an educator in the public school system to pursue a true “dream job” in the world of home staging and design. I wasn’t aware that I could make a living doing something that felt more like a fun hobby than a career, but I’m so grateful that I gave it a shot. Read more>>

Ashley Ebbert

Yes! I LOVE being a business owner! I’ve never liked being told what to do so being my own boss is exactly what’s best for me. The long hours are tiring & im constantly on my phone replying to emails, messages & managing social media but i wouldn’t change it for anything. After being a stay-at-home mom for years, i began to think i wasn’t going to have a purpose in life. Ramblin’ Rounds really helped me find who i am again. Read more>>

Malena Magnolia

I have this thought regularly! Particularly, during tax season and when times are tough like they have been within the last year. During tax season, I often dream about being able to just submit a W2 to my tax professional. That would just be so simple with less time and effort! Additionally, I started my business in 2017 and had seen growth every subsequent year. 2021 was my best year on record. I became a verified top seller on Depop. I sold clothing pieces to the sets of a couple tv shows and most importantly, I was finally feeling comfortable financially. Read more>>

Hollie Leggett

I often grapple with the idea of what my life would look like if I didn’t take up photography right when I graduated high school. I wonder what it would look like for me to come home from a job at the end of the night and not have to keep thinking about work. While I am still a student, I am incredibly grateful for the opportunity to work for myself, creating my hours and doing what I love. But there is still a part of me that wishes I could just be a student. Sometimes it feels as if I am not succeeding at either role. Read more>>

Kim Beebe

I am absolutely happier as a business owner! I have been working for other people since I was 15 years old. I’m now 36. I started my business back in January 2019 because I was sick of working for other people for crappy pay, and I was sick of not seeing my family. Don’t get me wrong, there were jobs I’ve had that I quite liked, but something was always missing. Then when I had kids, it was so difficult to get off in any instances where they were sick, or didn’t have school, etc. Read more>>

Joshua Alexander

I LOVE being an entrepreneur and a freelancer. I love that fact that it’s MINE, and no one else’s….that I rise or fall on my own merits, and am not dependent on anyone else’s success for my own. Yes, there are benefits and some might say security from being a W-2 employee at a given company. Conversely, as a business owner you need to find your own health insurance, for example. Read more>>

Joseph Bott

Several months back, I received a letter from a couple in another state letting me know they were interested in purchasing my business from me. I had not given much thought to selling my business as I love the studio and the many customers who visit. As I talked with the couple several times, they arrived at an offer that they formally sent me and my wife for us to consider. It was one of those offers that you have to stop and look at several times and make sure you read it correctly. Read more>>

Stephanie Davis

I have said quite a few times on this journey that I miss having a steady paycheck. I usually laugh right after I say it, but its a brutal reality when you own a business. I am very happy as a business owner because I am in complete control and whatever happens is solely because of me. However, I do miss the normalcy of a traditional job, with coworkers and lunch breaks and paid time off. Even though I don’t have those perks as a small business owner, I am absolutely more fulfilled working for myself versus working for an employer. Read more>>

Ana Arriaga

Owning a business has its ups and downs. There’s a satisfying feeling being able to make any decision you choose every day. You answer to your customers, but ultimately you decide what direction to take your brand and how it’s going to be represented. Happiness comes from working long hard hours, often with no sleep, and presenting a finished product to someone who is elated to receive it. When someone is excited and tells you that they are obsessed with your brand, or that they’ve driven 4 hours just to come to a pop-up, it makes you feel like every sacrifice is so worth it. Read more>>

Casey Simmons

I miss travel and leisurely meals. I think I could have been a good travel and food writer, blogger, or created a social media travel channel. Discovering new stuff is my passion. Meeting new people, experiencing new cultures, sharing ideas, trying new things, and collecting interesting stuff makes be happy. I daydream about being “on the move”, and finding myself in unexpected places. I crave authenticity. I am good story teller. So, I often think about heading out into the wild blue yonder. Read more>>

Amanda Zitting

I’ve always had “regular jobs,” and when Louise’s Granola Co was started, I was working full-time in a hospital during the onset of the COVID-19 pandemic. When I’m my most confident self (which takes a lot of self-work to be when you battle with perfectionism, haha), I know that I was highly valuable in most of my previous work settings as an employee. I am highly dependable and adaptable in the work setting. Read more>>

Tamara Wilson

I am happier as a business owner because for years I’ve told myself: “Someday I’m going to own my own business because I am tired of having to answer to a supervisor & clock in on someone else’s time clock everyday.” I’ve definitely had a thought in getting a regular job lately because of business being slow at times and I am one to always have income coming in. I have been working since age 14, so I’m not used to not working. Read more>>

Teriah Whitlock

As we all may know, being a business owner is far from easy. We wear several different hats, such as marketer, accountant, and customer service rep amongst many other things. The life is tough mentally and physically, and some days I wonder if i’ve chosen the right path. I ask myself, is all the stress worth it? Would I be happier working for someone else and no longer dealing with the overhead that comes with running a business. Read more>>

Isaiah Gills

As a business owner, I am happier than I would be working a regular job. I have been both in a regular job and have tried to make photography a full time job. My journey did not start with photography, but I am glad it made it here. I graduated college in 2017 from Wagner College with a bachelors degree in physics not knowing what I would do with it. I got in to coaching mainly because it was all I really knew and a local program needed some help. Read more>>

Becky Abplanalp

Being a business owner, is so much more stressful than I had anticipated, but also so rewarding. Building homes during Covid and Post-covid has been extremely challenging due to rising cost in material and labor. It was very stressful to navigate. There was once or twice, I had the thought, “I’d sure sleep better, if I had a regular paying job.” That thought was easy to push aside, because I love being a business owner. I love watching my company grow. I love to set goals and my team to accomplish those goals. Read more>>

Zoraa Gbeintor

Absolutely. There’s definitely highs and lows to having a business, but overall it’s been worth it. And I actually do still have a regular job. I’m in a stage where my business doesn’t fully bring me in the revenue I need to solely live off of (yet), so I currently still work full time. But luckily I work a hybrid schedule for my job where I’m only on-site 2 days a week and I can still pour heavily into building my brand. Read more>>

John Michael Morgan

I think every business owner has had moments or days when they think about packing it all up and getting a regular job. I’ve had those thoughts but they never last more than a few seconds. The truth is, I couldn’t be happier as a business owner. The risks and stress are worth it. Freedom is my greatest motivator. All the hard work of running a business is paid off with the ability to travel whenever I want. I get to spend more time with my kids. Read more>>

Samantha Strazanac

This is a complex question to answer. Most days, I love being a business owner and am very happy, but other days, I’m stressed and concerned I made the wrong decision to work for myself without stability rather than having a stable full-time job with a salary. Managing a staff, being an expert in my field, and maintaining client satisfaction all at once is HARD, then managing the business finances, HR, and sales is a whole other complexity of the business. While I have a staff, they can only do so much during their work hours. Read more>>

Karen Alpert

Being an influencer and business owner is a constant job. Sometimes I dream about clocking into an 10-hour job and leaving it both physically and mentally at the end of the day. But then I’m on vacation posting pictures from the top of a mountain, and I realize how lucky I am. My mind is always on my job, but I get to do it from amazing places—sometimes that’s from a canyon, or a sandy beach, or the middle school gymnasium where I’m watching my daughter’s choir perform. Overall, it’s a huge blessing that I’m my own boss, and there may be disadvantages, but mostly it’s pretty darn awesome. Read more>>

Tyelur Watkins

I am extremely happy as a business owner. Most people want to own their own business so they can make all the money in the world. That was not my goal. While being an employee there was always the contradiction of having to work for someone that didn’t believe in what I believed in (to some degree). A lot of my jobs were fantastic. I didn’t agree with the idea to work somewhere even though you hate it. So even though I didn’t agree with every process, placement, service, reason, etc. I still enjoyed whatever I was doing for 40 hours a week. If I didn’t, then I started seeking other employment. Read more>>

Jeremy Sanders

Owning a business is definitely tough and not for the faint of heart! There’s been plenty of times when I’ve told myself it would be easier if I just got a regular 9-5! Between logistics (planning & scheduling), retaining dependable employees, accommodating my crew’s concerns so they’re satisfied, complaints, unhappy customers, claims, backend costs, keeping up to date equipment, and then of course juggling my personal life. All while trying to keep the overall morale in good space, is always a struggle. Moving is tough not only for our clients prospective, dealing with closing delays, switching environments with school and work, moving is very stressful! Read more>>

Brittany Hunkin

I absolutely LOVE being a business owner and the life I have been able to create being one. But, I’d be lying if I didn’t think having a “regular” job would be easier. The ideas of leaving work on a Friday and not bringing work home with you, being taken seriously as a “real” working woman, and being able to actual get work done, sounds so appealing. But after much consideration I know that I’m far happier as a business owner than if I worked at a “regular” job. Read more>>

Charlene Young

Business ownership is tough. I left the Data Analytics world to pursue my passion of making Filipino BBQ accessible throughout the entire United States. I didn’t want to work for “the man,” I wanted to work for myself. My stride is good. My partner (who happens to also be my husband) and I are hard workers and share in this dream. So, in the first year of dabbling into Consumer Packaged Goods we made it into a major grocery store chain — putting our brand’s smoked Longganisa (Filipino style sausages) into 69 groceries throughout 2 states. Read more>>

Ilysha Thompson

I would definitely say I’m happier being a business owner ten toes down. Being able to work and get paid doing something you love is different then just clocking in to work a 9 to 5 and be bored. To be a full time artist is my dream and it takes time. But usually working for someone else and big corporations they want you to do a lot of work for minimum pay. But working for yourself you get to have a lot more fun. Read more>>

Hannah Fales

Owning a business has so many challenges, but it is also so rewarding. Especially in floral design. You meet with the client for concept and ideas and then months later, you make their dreams come true. I get to step back and look at the work I did and be proud. There have been many times where a client has asked me to do something I have never done before and I surprise myself with the result- I did that and I rocked it! Read more>>

Abigail Coale

I wonder what it would be like to have a 9-5 job nearly every week. When people think about owning a business, they probably think first and foremost about being their own boss, in charge of their own schedule, but I don’t think they think about all the challenges that come along with it. Read more>>

Sheryl Henderson

As a business owner, you are faced with many challenges, which sometimes leave you questioning did you make the right decision when choosing to leave the security and structure of a job. Unfortunately, I am not exempt from those feeling and even acted on them once. In 2014, after two years in business, I was in debt and experiencing financial hardship. I would like to say that this was no fault of my own, but honestly, I would be lying. In 2012, I launched Dynamic Beauty and Supply LLC with the idea of selling hair bundles. Read more>>

Samantha Alfonso

I’m definitely happy as a business owner. I do have those days when I wish I could just clock out and not think about work. Owning a business is like being a parent. It’s 24/7. It’s a lot of worry and a huge commitment. At least it is if you want to be really successful. My problems can’t become my staffs problems but all of theirs become mine. I try to be the kind of boss that meets my teams needs and can be flexible within reason. Read more>>

Sara Godfrey

I have been a free spirit for as long as I can remember, marching to the beat of my own drum, wanting so badly to freely be myself, in all aspects of life….Especially my creative side. Being creative was and is in my core. I believe all of us are here to “create” in some regard, so it was an incredible discovery when I realized that homes were my passion. All things homes…the exterior design, the way they make you feel, the questions or emotions that they provide. Read more>>

Brit Adgie

I love being a business owner. There are so many aspects of my life I now have full control over but with that freedom comes stress of the unknown. I don’t think I was fully prepared for the level of stress starting a business can bring. From obsessing over your cash flow to training new employees, everything starts and stops with you. You have to be sales, marketing, office admin, trainer and (in my case) photographer and editor all in one. Read more>>

Kyri Burke

I’m extremely satisfied and happier with being a full-time entrepreneur and business owner . I often think about what it would be like if I stayed in corporate America and worked a regular 9 to 5 job . There wasn’t much satisfaction or fulfillment working in corporate America I always felt like something was missing I always knew that I was destined and purposed to do something much more passionate that spoke to the identity of who I really am . Read more>>

Alexsia Brown

I am 100% happier as a business owner versus when I worked for someone. I’ve had regular jobs in the past, and it was just always a schedule conflict, there wasn’t any room for growth, and I always in the back of my head thought this is not where I want to be. From 2017 to 2021, I was working jobs (except for two, which were a senior graduation photography company and a newborn photography company) that were not particularly anything I was interested in, but more so survival. Read more>>

Sherlette Lewis

Being a business owner is the BEST thing that has ever happened in my life! It brings nothing but peace and joy being my own boss and being able to service people as I make a difference in their life. I remember when I was able to quit my job February 2021. I was MISERABLE! I had a horrible boss, I was overworked, under appreciated and I wouldn’t have the energy when I came home to dedicate it to my son. I only had time to spend with him as I was getting him together for school or getting him ready for bed. Read more>>

Kimberly Epps

I am so glad that this was a question for this interview. Being a business owner is a 24/7 job that sometimes I wish I could just clock out of. Some of the main issues that arise in my field don’t typically happen during normal business hours. I manage all of the housing needs for productions as well as private investment properties for over 30 investors in various states and countries. Needless to say, work never stops. Read more>>

Angelica Sammons

I can honestly say, being a business owner is both a blessing and less than ideal. It comes with both pros and cons. The last time I considered entering the world as an employee working for someone else, was a very tumultuous time in my life. Some major life changes had taken place. A major housefire decimated my life. It took a toll on my family. Seemed more than i could handle alone with multiple businesses running, and 4 kids at home. I scaled back closing one location to go home for a mental health break. Spent the summer with my family. Read more>>

Dr. Marquita S. Blades

Whenever I’m out in schools working with educators, it always makes me miss being in a school building full-time. I even think about what it would be like to go back into the classroom again, but those thoughts are always short-lived. Not because I don’t love teaching – I absolutely DO – but there is a lot that comes with teaching full-time! Whenever I miss the classroom, I am also reminded of how much I struggled during my final years in the classroom. Read more>>

Bishop Daniels

As a business owner in the fitness (health & wellness) industry, I’ve played every role their is. I started off pretty much interning for another business owner/trainer. While learning the ins and outs of the business it immediately put me in the mindset of becoming a business owner and creating a better path for myself and others. I’ve only ever had two jobs in my life before becoming a trainer, Assistant director at a community center and Playing basketball professionally. Read more>>

Nicholas Mitchell

I’ve thought about this topic on multiple occasions throughout my journey as an entrepreneur. Ownership is a concept that is very important to me and something I hope to past down to future generations of my family. I can definitely say that I’m happier as a business owner than working a regular job. With that being said, I can’t deny the lessons and skills I’ve learned in Corporate America as well. Each have their own list of pros and cons that could be argued are better than the other, Read more>>