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.

Shailyn Ramsey

Growing up, I always wanted to have my own business(s) or work at a big corporation. I once dreamed of having a 9am-5pm job with my own desk, a set salary, constant promotions and wearing business attire everyday! I also dreamed of having my own business of some sort. I based many of my life decisions on making sure I was well educated and was able to attain certain degrees to be successful in the business world. Read more>>

Michelle Shveta Dhillon

As a South Asian Female, first generation American born, I can tell you, as many of my peers in the same category will agree, your career path has likely been selected for you. Being an entrepreneur was definitely not one of them. My parents migrated to the US in the early 80s, first generation to leave their home and family behind to do something different. That puts a lot of pressure on them as parents, and on us as kids to make sure we all succeed. When you come from an upper middle class family, the need to go elsewhere to build a future was unnecessary. Read more>>

Danielle Michel

Definitely, being a business owner brings an unparalleled sense of fulfillment and autonomy like nothing else. But it doesn’t mean it’s been easy. Even when I was climbing high in the corporate world, my entrepreneurial spirit never faded. My brain was always buzzing with business ideas and inventions. Yet, even when contemplating the security and comfort that comes with a regular job, I wasn’t tempted away from the aspiration of being a business owner, even more so during challenging times. Read more>>

Devina Serpentine

I genuinely am happier as a business owner, working for myself, doing what I love & what I am passionate about, running things my way, and working the hours that I am wanting to work, charging prices that value my worth & that reflect my level of expertise rather than working for minimum wage or working for a company that I do not align values with, or giving all my time away and trading 8 hours of my day for dollars. I don’t think everyone is built for entrepreneurship or for running their own business, I believe anyone with the right mindset can do it, and I believe if you have big dreams & visions you should 100% pursue them. Read more>>

Erik Quigley

My husband and I have a toddler, so this question has come to the forefront several times as he’s gotten older. I was a very loyal W-2 employee in the years leading up to freelancing gigs and then morphing into a creative agency with multiple dba’s. I remember the security of the ‘regular job’ lifestyle; I also remember COVID, and the layoffs, and the uncertainty. Being a business owner has it’s ups and downs (sometimes minute to minute), especially when you’re in your infancy, but at least I’m in control–I’m not waiting for someone else to pull the rug out. Read more>>

Karine Cruz

As a business owner, these questions often swirl in my mind. The life of a small business owner is a constant juggling act, filled with inquiries like “What is next?” and “How can I expand the business?” The relentless pursuit of acquiring more clients is a demanding aspect of entrepreneurship, and the weight of knowing that my income relies entirely on securing these clients can be, at times, overwhelming. Read more>>

Britt Brashear

I’ve been so happy as a business owner and wedding planner – most days! For 11 years I had a regular job as an elementary school teacher. There have been a lot of ups and downs as I’ve transitioned to becoming a business owner and I’ve questioned whether it was the right thing to do many times. Switching careers and having so much to learn was daunting. It was also difficult not having a consistent paycheck even though I was working all the time. Read more>>

Nia Brown

Overall, I am happy as a business owner. Of course I have my days where I dread going into my shop, but once my client gets there and we start to vibe, all of that changes and it makes me remember why I went into this profession in the first place. Making people happy and feel beautiful, makes me happy! I feel like I was put here to serve, and that’s exactly what I’m doing. Every once in a blue moon, I do dwell on what it would be like to work a regular job, to have a set schedule, to have a consistent paycheck..but the work I do is so much more fulfilling. Read more>>

Matt Gruber

I think this is a natural thing to question yourself as a business owner. Being a business owner- especially in a creative field- can be rewarding, fulfilling, and nothing short of an existential life crisis all in one day. Despite all of this, I could never see myself doing anything else. At it’s best, you feel like you are on top of the world. You are expressing yourself creatively, you are making your clients happy, and you are full speed ahead with no plans on stopping! At its worst, you feel like a failure, you take every minor complaint or issue to heart, and it will always feel like the end of the world. For many creative small-business owners, there is no in between; you are either on top of the world or you are drowning in panic. Read more>>

Lauren Pascal

Happiness and business owner are synonymous in the dictionary of my life. Honestly, I never knew I would become a business owner but once I did, it’s like when Cinderella placed her foot in her glass slipper, it fit perfectly. As a little girl, my whole family would tell me I was bossy and a tad bit controlling so becoming a boss, where I have full control over an entire company is very fitting! Before my business, all I did was work regular jobs and although I do not miss working for others, at times I miss the stability it brings. When you work for someone else, you know when you’re getting your paycheck and how much it’ll be. Read more>>

DEBORAH KEATON

Am I happy as a business owner… Mostly. I love being my own boss. I love being able to work wherever I want. I love the variety. I don’t love the down times. I don’t love the self-employment tax. I was on staff a few times in my career. The most significant time was at Disney. I started as a freelancer and they kept asking me to come on staff. I resisted and said to myself and the universe. “The only way I’ll come on staff is if they make me a creative director” Well that was a powerful thing to do because the very next day that’s exactly what happened. (I wish that worked with the lottery) Read more>>

Kat Thongnoppakun

3 years ago I left my corporate engineering career path to pursue food entrepreneurship. People are usually curious about my situation and ask me. How and when did I know I was ready to make the jump? I’ll be honest. I wasn’t really ready. During Covid, my trajectory shifted when I got laid off as a contracted Aerospace Engineer, and instead of continuing down the path, I decided to walk down a different path. I got offers to continue being an engineer, but I knew for a while that wasn’t what I truly wanted to do. Read more>>

Sadie Fienberg

All in all, running my own business is an amazing experience, but, as with everything, there are pros and cons. Being my own boss allows me the freedom to control every aspect of my business but it also brings some unpredictability. Being an entrepreneur means I have to handle a wide range of responsibilities. In a regular job, things like pay, benefits, and schedules are typically taken care of for you. Transitioning into the world of independent business ownership made me realize the lack of security and structure that traditional employment offers. Nonetheless, the flexibility and independence I’ve gained from being my own boss make the challenges well worth it. Read more>>

Andrea Williams

I absolutely LOVE being a business owner. From choosing my own hours, no dress code to follow or worrying about upsetting my boss. It’s amazing to have the freedom to choose what course I want for myself and the direction of my business. I just wish I had done this sooner with my career. It is always a rolling joke with my customers about how my “boss” never gives me vacation time. Since I am my own boss, I am always working. My brain is always turned ON, too new ideas and what needs completed that day, week or month. Read more>>

Brooke ODell

Being a business owner is not for the faint of heart. I have heard that phrase my whole life. It’s similar to hearing the phrase “c-section” and not fully understanding the layers and complications of having a major surgery, you just know that the end result is a precious baby. Being a business owner of a small independent retailer who has survived a world shutdown and COVID-19 in the midst of one of our worst recessions, plus physically relocating and expanding a business is another fun event all in itself. I wonder to myself daily what it might be like to have a job I can walk away from at the end of the day, a job that doesn’t demand round-the-clock attention, stress, emails, questions, problem-solving. Read more>>

Angela Robinson

Am I happier being an business owner? Yes I am. I enjoy making my own schedule. I enjoy the extra free time I have to be a full time mother and I also like being my own boss. Yes I do think about having a regular job all the time. I miss the consistency. I miss being around others and working 8hr shifts. I think about getting a regular job all the time then someone needs me. I always go from no appointments booked to all available days filled up in a matter of hours or no sales for 2 weeks then boom sold out… Read more>>

Olivia Boyd

I am happy as a business owner. It is the most challenging yet most rewarding thing I have ever done. I struggled a lot (and still do sometimes) with not leaning onto a corporate job as a safety net. I like the idea of working a 9-5 to supplement my business, even though it would require my time to be divided. I think it’s all about what you can handle and the status of your business or career. Where I currently am in my life, I think it’s very important to feel fulfilled. We all have to do things we don’t like but life is meant to be enjoyed, however that looks and feels like to you. Read more>>

Jamie Miles

Having had a regular job for many years, I finally decided to take my leap of faith and say goodbye to toxic corporate America by becoming fully self-employed. I’m an Actor, an Influencer, and a REALTOR®. with Keller Williams Atlanta Midtown. My previous job was becoming toxic and I knew I needed a change, and let’s just say they gave me just enough BS for me to say nope, I am better than this. So I left.. Read more>>

Fernanda Lizbeth Verduzco

I am happier being the owner of my company, but for now I continue with a job too, it is very different to just focus on working for 8 hours than having to be 24-7 thinking about what to do to grow your business, yes it is more hard but you enjoy every step Read more>>

Laura Patrick

Immeasurably. As an owner of a large-scale German inspired bar and restaurant (Bay Street Biergarten), a freelance attorney, and a member of multiple other “make your own schedule” ventures for over 10 years, I honestly can’t fathom having a “regular,” job. One of the driving factors of opening up my own restaurant with my two operating partners, was to avoid sitting at a desk from 9-5. Don’t get me wrong, I don’t look down on anyone who has a “regular job!” Read more>>

Ebay Fuller

I Am Happy Being A Business Owner, As We All Know It Can Be Quite Stressful, But I Know A 9-5 Was Just Not Meant For Me. I Definitely At A Point Felt Like I Was Ignoring My Purpose For Sometime; Once I Gave In To My Purpose & Passion, Things Started To Happen For Me And That Was My Reassurance. Read more>>

Leanora Babb-Benjamin

Yes and I believe that this is what I was destined to do. Although my previous roles which were regular jobs had some elements which were fulfilling, qualifying and working as a Clinical Hypnotherapist provides me with a deep sense of satisfaction and overall feeling of a job well done when seeing the changes in clients. Whenever clients engage with the process, they commit to change and I know that they have entrusted me with their vulnerability to help them become a better version of themselves, this makes my work very rewarding to me as well as humbling. Read more>>

Dmytro Ushakov

I am very happy as a business owner! The happiest thing for me and my family is that we are here in USA. In the country of successful and rich people, in the country of small business, here you can realize any of your dreams, if you really want and work on it! Of course, I could work at a regular job and do a narrow direction in construction. But I am a jack of all trades, I can do almost anything! I know how and what can be replaced and repaired. I see the result in my head long before the work and can explain to the client ! If I had a regular job, I would be bored. But now I build and plan my every day and what I will do! Read more>>

Bunny Hou

So I actually still work full time with a “regular job” in addition to running my business however, hoping that one day this will change! However, I did have to quit my phlebotomist job and find a job where I can work from home in order to have more time for my business. I really enjoyed serving my community, helping others and working directly with patients but I knew that Hazy Bunny was my purpose, my baby, etc and I knew I had to make some sacrifices in order to ensure I can uplift my business. Read more>>