So you want to be an entrepreneur?
Giving up the 9-to-5 and becoming your own boss is no small feat. It takes intelligence, heart, intuitiveness, tenacity, foresight, and a heck of a lot of courage. Most people who pursue entrepreneurship say it’s the hardest thing they have ever done. However, most also say that it was the best decision they ever made.
I myself have to agree.
One mistake that would-be entrepreneurs often make is that they look at someone successful and say, “I don’t have the skills, the network, the finances, the abilities, the time, the resources, etc. to do what that person is doing.” This is called the scarcity mindset, and it works hard to keep you right smack-dab where you are.
Take me, for example. It wasn’t until after years of sitting behind a sea of data in a federal government office employed as a senior economist (feeling miserable and lost) that I built up the courage to take the necessary actions towards 1.) becoming my own boss and founding my own executive life coaching company, , 2.) making a positive impact on peoples’ lives every day, 3.) having a hands-on role in , and 4.) feeling complete satisfaction and happiness with who I am, what I do, and what kind of lifestyle I lead. This change was incremental.
Whether you are a student, a corporate slave feeling bored and tired, or a budding entrepreneur wondering whether you have “what it takes” to succeed, the eclectic stories of these 25 entrepreneurs demonstrate that it simply takes perseverance through fears, failures, obstacles, challenges, and bumps along to road in order to realize your dream.
Take it from these 25 daredevils who have shared a little bit about how becoming an entrepreneur has changed their lives—in both challenging and rewarding ways.
- Francesca Montillo, Founder of Lazy Italian Culinary Adventures, LLC
“Becoming an entrepreneur is life changing in every aspect. If you’re unsatisfied working for someone else, the satisfaction of running your own business is like nothing else. Even the best job you’ve ever had can’t compare to the feeling of being your own boss. It can never be compared to working for others. It consumes you, sometimes in a good way, sometimes not. Your business is on your mind 24/7, there is no work-life balance, but the beauty is if you love what you do, you don’t mind.
On a positive note – you feel in control of your destiny; on a negative note, you are in control of your destiny! There is lots of wasted time in a new business so you might confuse busyness with productivity. On a social level, you might miss the daily office interactions of catching up with co-workers, so it’s important to surround yourself with other like-minded individuals.
Entrepreneurs are by nature a bit rebellious, so the everyday 9-5 can feel like torture. For me, I became healthier when I started my own business. I had time to arrange my schedule so that I could fit in walking and exercising. I don’t work 8 straights hours and can break in between for a walk or errand and pick right back up where I left off without feeling less productive. It impacts your lifestyle in every way…”
- Jennifer Devlin Waller, Founder & CEO of Celtic Complexion Luxury Artisan Skincare
“Being an entrepreneur is like being a real life MacGyver; you must be able to have at least a working knowledge of every single aspect of your business. I believe entrepreneurship embodies the true American spirit, because at the end of the day it provides a certain freedom that cannot be matched by a corporate 9-5 job. When you have the ability to adapt to any situation, ride the highs and lows and influence people, it gives you incredible confidence that translates to all other aspects of your life.
The downside is that it’s lonely. Friends who have corporate jobs can’t relate to your challenges, so there is no “shop talk.” I do miss that camaraderie of an office.
The best thing being an entrepreneur has given me is time. Time to spend with those that mean the most to me, time to pursue my interests (glamping) and time to take care of myself.”
- James Bennett, Founder of FireFly Team Events
“I love what I do. There was a challenge and a sense of purpose that I never found working for someone else. It’s not black and white though. As an unsuccessful entrepreneur it was much harder to make a happiness claim. As I’ve grown to be successful I can breathe deep and smile with confidence. I’ve found where I’m supposed to be. Purpose, true purpose is an amazing dopamine rush.
My current role gives me puzzles, tasks, creativity problems, and I soak it all up with a smile. But the danger is that I burn all of my creativity and brain cells in the name of the business. My personal creative projects remain ideas because I don’t have the energy left for them. It’s ridiculously easy to never take your mind off the business when it’s yours. I’m working on giving myself permission to back off. I’m learning to make conversations with my fiancée about things other than work. I’ve learned that the reason I’m being creative affects my happiness in different ways. I also learned that I REALLY like giving other people purpose as an employer.”
- Jeremy Schaedler, Founder and President of Schaedler Insurance Agency, Inc.
“Becoming an entrepreneur has impacted my personal and professional life in many different ways, but what sticks out the most is that it has made me accountable for my time and actions. Punching the clock in a 9-5 did not require me to always bring my “A” game because there was neither great rewards for achieving excellence nor great consequences for being mediocre so long as my production was in line with my co-workers.
Becoming an entrepreneur changed everything in the sense that, if I slack off, my business may fail and my family will pay the consequences, so bringing my “A” game on a daily basis allows me to reap the rewards of my actions. Once a person realizes they are in charge of their business destiny, they also realize they are in charge of their personal destiny and often make lifestyle choices in line with those values. Some entrepreneurs may value nice homes and flashy cars, while others may prefer a more conservative approach such as spending more time with family.
What makes being an entrepreneur great is it gives a person the freedom to choose the direction of their personal and professional life.”
- Christy Cook, Founder & CEO of Teach My
“Personally, being an entrepreneur is empowering and has provided a sense of purpose. I have become an inspiration for many other women entrepreneurs and a role model to my son. Every day, I cherish the flexibility I have as an entrepreneur. I rarely miss school drop-off, pick-up, homework time and school events because I can make business decisions and build a successful company on my time. Also, my role as an entrepreneur earns respect within the family. We are all equals working together to create a better life.
Professionally, being an entrepreneur has instilled self-confidence. My work-self from 10 years ago resembles nothing of my new work-self! I have learned to make decisions quickly and to take educated risks. I have learned the importance of grit, passion and resilience. The new me is strong and self-assured. I have proven that I can make good decisions, build a successful business, maintain balance and have a harmonious home life.”
- Nishchal Dua, Founder of The Remote Life
“An entrepreneur can hear ‘No,’ see their work of months fail big time & do 37 different tasks with different parts of the brain & skills at the same time, all with a smile on their face. Why? Because we know what life really is. We know our place in the bigger scheme of things and we know that the world won’t end if a deal doesn’t go through or we don’t get that promotion or can’t buy our dream house or car. You get used to rejections, failures and doing things under stress. It gives you a perspective on life that a regular job just cannot. Entrepreneurs enjoy the journey; 9-to-5 people are waiting to reach their destination, forgetting to live in the moment.”
- Sarah Sekula, Freelance Journalist
“I escaped cubicle life in 2009. These days, as a freelance travel journalist, I focus solely on projects that are fulfilling to me, have the freedom to work from anywhere and have control over my schedule, which means I can easily avoid rush-hour traffic. As a result, my stress level has gone way down.
Most days I wake up really excited about the projects I will tackle. Better yet, if I want to work on a Saturday morning instead of Friday afternoon, I do that. I also appreciate the fact that my compensation is a result of how much work I put in. The downfall is not having coworkers. But I solve that problem by setting up lunch meetings when I need some brainstorming sessions. “
- Tim McCabe, Creative Director and Cofounder of CardFool
“Being a boss has given me the luxury to be surrounded by a team of artists and writers who value humor just as much as I do. Now I enjoy going into a brainstorm. Laughter is part of my job description now.
The reward has been taking time to laugh. Look at our world, look at all that’s going on not only abroad but also in people’s everyday lives. We want to make people laugh and we believe that CardFool succeeds in bringing humor to people’s lives. I have a friend that uses CardFool almost daily to send funny, add-your-own-photo printed cards and eCards to her friends from trips they went on, nights out etc. She told me recently that her friends always say to her, “You are so thoughtful – what a surprise to get a gift like that!” She says we make her look good. We want to keep doing that…and making people laugh.”
- Scott K. Curry, Founder & CEO of Scott’s Marketplace
“As a startup entrepreneur, the journey is all about your passion. It’s exhilarating and exhausting—but the separation of “personally” and “professionally” is what it’s not. It’s blended. It’s intertwined. In a moment, I’m Dad, I’m husband or I’m a friend. In the next moment, I’m the boss, the mentor, or the colleague. There is no delineation between personal and professional as a startup entrepreneur. In today’s world, you never turn it off, so an entrepreneur must learn to balance a variety of roles throughout each day.
The challenge of the unknown is always present for an entrepreneur because there is no clear-cut path. With hard work and family support, you are rewarded with your vision coming to life. You get to live your passion while being involved in the lives of those who are important to you, which are the truly rewarding parts of entrepreneurship.”
- Fred Schonenberg, Founder & CEO of VentureFuel
“Most people think giving up the standard 9-5 workday means graduating to working less hours per day, but the reality is that you are simply trading a work day for a work life. The hardest part of becoming an entrepreneur is that work never shuts off and there are no more “days off.” You wake up, and work is the first thing that comes to mind no matter where you are. You even think about deals while you are skiing or out having fun with friends. That said, you now have the flexibility to be obsessive over your work anywhere you want to be. So, the greatest positive is that you don’t miss weddings or trips anymore because a boss won’t let you leave early – but make no mistake, you are always working on that plane or even as you sleep. It never shuts off, but if you love what you are doing, why would you want it to?”
11. Carolyn Wilman, Founder of Contest Queen
“I created my home-based business in 2004 when my daughter was 2. It was the best thing I did as it gave me the flexibility to be there when I needed to be and work at odd hours. I can’t believe my daughter is now 14 and in high school. Plus what I do is a lot of fun. My daughter doesn’t know a life without winning, prizes or crazy adventures.
The hardest part is not having a regular paycheck or benefits. It wasn’t as worrying when I was married, but once I got a divorce it was even more important to ensure a steady stream of clients, which isn’t always easy.”
- Björgvin Benediktsson, Founder of Audio Issues
“In summary, the most rewarding aspects of entrepreneurship is the freedom to work whenever and wherever you want. I’ve traveled the world, toured with my band and enjoyed extended ‘vacations’ all while earning passive income through my business. Also, not being constrained to a specific yearly income allows you to keep pushing to increase your income, and in return your quality of life!
Of course, the flipside is that you never really ‘turn off’ as you’re always thinking about your business. This isn’t necessarily a bad thing as long as you develop healthy habits to help you systemize your business around your life. Using outsourced help enables you free up time to work on the most creative aspects of your business while still growing.”
- Caroline Cecil, CEO & Founder of Caroline Cecil Textiles
“I have always been the type of person to give a lot of my time to my career, while my hours haven’t been 9-to-5 for sometime the energy and intensity at which I work has changed dramatically since starting Caroline Cecil Textiles. The main factor in this is the level of accountability required of me as an entrepreneur. The most rewarding change has been discovering my strengths and weaknesses as a “designtrepreneur”. As a textile designer I strive for a balance between my creative and business responsibilities and delegating tasks to my team. This is something that I think a lot of young entrepreneurs struggle with and from my experience, having an amazing support system is absolutely critical to success. I truly believe the act of working together as a team makes the concept, process and final product better, no matter the task.
As my company Caroline Cecil Textiles has grown, I’ve definitely seen the amount of difficult days increase but at the same time so have the amount of incredible ones! Becoming my own boss has been both a humbling and rich experience, but the biggest skill I have learned is my ability to work smarter!”
- Camilla Ley Valentin, a Danish co-founder of Queue-it
“One major positive change that came from starting my own company is that I am now the manager of my own time. While I certainly don’t work less as an entrepreneur, I now have the flexibility to make a doctor’s appointment midday, attend networking events, and so on. What I appreciate most is the fact that we have built this amazing, international team from what started as merely an idea, as well as being able to build a truly meaningful product that creates online fairness for everyone. The only thing I consider to be a hardship in this process is having limited finances for both the company and personally.
That said, I do feel that my life has actually become less stressful after starting my own company. It’s great to always be in the know when it comes to my work situation, and to be able to directly impact results and take action in a timely manner when necessary. Lastly, I’ve learned that building a strong business network is key, as people are surprisingly very willing to help out when you’re starting your own company, and there is no one better to learn from than veteran entrepreneurs themselves.”
- Emily Ley, Founder and Creative Director of Emily Ley Paper & Gifts
“Before becoming an entrepreneur, I had a career in the corporate world. At that point in my life, success to me looked like having my name in lights. But now, as a mom of three – including twins, an author, and a business owner, success looks like having the flexibility to chaperone a kindergarten field trip to the zoo on Thursdays. Running my own company gives me the flexibility to be present for the things that truly matter and fulfill one of my greatest professional goals – creating purposeful products to help empower women. I’ve learned, both personally and professionally, that slowing down is where life is the sweetest and where you have margin for the things that truly matter.
Diving into the field of product design and production was a whole new experience for me, and one that came with many unexpected difficulties. Early on I messed up and fell on my face a lot. Most notably, during the early phase of my company, I made a massive production mistake that ended up costing me $6,000 worth of product. I doubted myself a lot afterwards and thought maybe I wasn’t cut out for this. But, I got back up, decided to give it another try and I’m forever glad that I did. Without that mistake, I might not have Emily Ley Paper & Gifts as it is today. “
- Bilal Kaiser, Founder at Agency Guacamole
“After working for some really big companies during my marketing career (L’Oreal, Sony Pictures), giving up a 9-to-5 gig completely changed my life both personally and professionally.
First, the great things: Breaking away from a fast-paced, often political corporate environment allowed me to invest in myself. Over the last 12 months I’ve been able to start meditating, be more present, work out more and spend more time with my partner and our kitties. The results? Lower stress levels, more creativity for projects and much more excitement for getting things done. I get to work from home, my fave coffee shop or even from a secluded desert bungalow. The freedom to not have to ask anyone’s permission to do this is immensely gratifying.
Next, the challenges: Everything falls on me. Not just deliverables and due dates, but administrative things like accounting, legal forms, IT issues—you name it! This can be both daunting and exhausting, but the reality is that things need to get done and that’s what entrepreneurs do. I miss the perks of working at large companies. From company travel agents to access to data sets and digital tools, as an entrepreneur I’m much more limited in what I have and what I can offer to employees. (Luckily I have friends who work in corporate who sometimes share goodies!)”
- Renee Hansen, founder of Hipcycle
Rewards: “I’m watching the business grow and know that I’m directly impacting it. I’m also bringing additional social value to the world. It allows me to more easily pivot between my work and personal life. It’s something I can be proud of because entrepreneurship is something that most people don’t have the guts to do because it takes away a lot of security.”
Unexpected Difficulties: “It’s even harder to “shut off” than my corporate days. Work fits into little nooks and crannies, but also weighs on me more. It’s harder to “let go” because I’ve put my heart, soul and every free moment into my businesses. Working on things that aren’t in my “wheelhouse” (can’t say “this isn’t part of my job” because EVERYTHING is part of my job). Explaining your “job” to others—because it’s not really a job—it’s bigger than that because it’s such a big part of your life.
In summary—entrepreneurship tends to be more of a marathon, rather than a series of shorter races. You have to start focused on endurance, not the sprint. You have to stay disciplined and focused on the end goal, rather than hiccups along the way. You have to be ready to fail and get back up and do it again. You have to be ok with vulnerability. You have to be ok with knowing that everything won’t be perfect, and nothing ever goes as planned. Most importantly, you have to find ways to make it work within the resources you have.”
- Ryan Croft, Co-Founder of TransitScreen
“I have been an entrepreneur from the start, so I never had to give up a traditional 9-5 job. It’s the only way I know. Motivations are totally different when you are working for something that is ‘yours.’ Having the ability to see the world (100 cities and >50 countries) was the most rewarding part of my previous startup, an adventure travel company.
With TransitScreen, the biggest challenge is managing growth and knowing when to say no to opportunities. We are inundated with exciting projects in every region of the world, but a founder’s job is to filter through the noise and choose opportunities that generate value. Seeing something you created have a positive impact on a single person’s life is a great feeling.”
- Henry Preiss, Founder & CEO of Preiss Imports
“I gave up the 9-to-5 just over 43 years ago, and have never once looked back. For me, the freedom of movement and expression to make business happen was necessary and that would not have worked in a typical 9-to-5 environment.
The difficulties are countless, from selling unknown brands, to financing, getting distributors interested and to making consumers aware of our offerings. What is always and will always be rewarding is when the new products we bring to the marketplace are embraced, and when we receive feedback on how much one of our customers enjoyed a certain product.
Unlike a traditional job where the amount you work and the specific duties are set, being your own boss becomes a dance in managing your time and allocating time where it is most needed. It’s a complex and difficult dance, and you must have your employees and outside contractors be part of the team in a way that moves the company forward.”
- Rony Chammas, Founder and CEO of Peerspace
“Professionally speaking, everything falls on your shoulders: the success of the company, the livelihood of your team members, and the customers that use your product. It is an immense amount of pressure and responsibility. Personally, I try to manage that stress by trying to stay healthy and relaxing while I’m away from work. One of the most important things I do away from work is spend time with family, as they are the support system that encourages me through the roller coaster ride that is entrepreneurship.
The biggest impact is that you are always working and it is nearly impossible to unplug and just focus on yourself. It is a reality that all entrepreneurs must face—that we have to give up a lot of personal time we once had in order to ensure the success of the business. I now wake up early to find some personal time for working out and reading the news because once the work day begins there is no way any personal time will occur.”
- John Rushworth, founder and CEO of Bottles Tonight
“Being an entrepreneur means a lot more perceived freedom, with a lot less freedom. It can be personally invasive but extremely rewarding both personally and professionally. The most positive and rewarding changes are when you slow down and realize you can keep the ship afloat or sink it. The company’s success rests on your shoulders, which motivates me to try harder and dig deeper to succeed. It is a powerful feeling!
Since success largely rests on your shoulders, being an entrepreneur can impact your social life, both in networking (a positive) and by being invasive in your personal and family life (work is 24/7). The challenge is how to fit it all in and try to find some balance.
Becoming my own boss has given me a schedule that is dependent on my own deliverables and success driven metrics. So it’s perceived flexibility, when in reality you must do what’s right for the business to succeed. Even if that means strange non-traditional work days. I road bike a lot in the San Francisco Bay Area which helps clear my mind while thinking through problems. Even though there is always something to do for BottlesTonight, it is essential to find those moments to unplug.”
- Ted Chan, Founder and CEO of CareDash
“Honestly, I was lost before I became an entrepreneur. I always took pride in working hard in my corporate roles, but building companies that have a positive social impact (like CareDash.com, which is dedicated to bringing trust and transparency to the healthcare review industry) is my passion. As an entrepreneur, there are never enough hours in the day, so I’ve learned to streamline every aspect of my life to really focus on the priorities in order to lead my team to the best of my ability. I’ve also learned that truly taking care of myself is critical to being productive and balanced. I’ve replaced fantasy football and half-effort gym workouts with intense runs and fitness classes. Being laser focused on accomplishing my goals has allowed me to eat and sleep better; I’ve even gone from a 24 minute 5K to targeting a Boston Marathon qualifying time this year.
My biggest unexpected difficulty has been an illness in the family that has made major demands on my time, while also having two kids since I started CareDash. I’d say, though, that even this challenge has only served to sharpen my focus and allocate my time more efficiently. Besides my team, my family is the other ultimate stakeholder in my work.
In my corporate life, I had a routine, but I wouldn’t say I was in control. As boss, I really feel responsible and accountable for spending every minute well. And whether that’s family time or work, I do my best to be 100% present, enjoy the ride and give it my all.”
- Doug Hirsch, Co-founder and Co-CEO of GoodRx
“Being an entrepreneur is simultaneously liberating and terrifying on a daily basis. When it’s your baby, it no longer a job; instead, it’s a 24/7 obsession, and it can be hard to find balance in your life for other things. Every decision carries the weight of not only the company’s future, but also your reputation and the livelihood of all the people who have chosen to join you on the journey. It’s beyond stressful and likely unhealthy…and I would do it all over again in a second.”
- Tina Aldatz & Margarita Floris, Co-Founders and CEOs of Savvy Travelers
“I’ve always had a problem with authority so choosing to run my own business came naturally… after paying my dues and working in the trenches of fashion, tech, tires & rims to lingerie… whatever it was, I understood it was a business. You’ve got to be a certain kind of crazy to take on running your own business—not to mention the pressure of knowing that you’re responsible for other people’s families: putting food on their table, health insurance, and the list goes on and on. At the end of the day, knowing that you’ve truly created an environment of culture and family and knowing that you’re leading people to accomplish their goals or find their passion is more rewarding than words can express. It’s important to know what you’re good at, but more important to know what you’re not good at – then build that team!” – Tina
“As an entrepreneur, especially in the first 5 years of your business time is not measured. You are either working or thinking about work every waking moment. We have been called Brave, Crazy, Risk Takers…but when you are building a company that you are passionate about and wholeheartedly believe in, there really is no better feeling—yes, even when it’s hard and you wonder how you are going to make it through another day. I feel that there is a strong similarity between entrepreneurs and Dare Devils, there is a thrill at taking big risks that gives us the adrenaline to think outside of the box and use all of our resources in order to land on our feel. It is not for the faint at heart.” – Margarita Floris
- Crystal Stranger, EA, Founder and President of 1st Tax
“Being an entrepreneur is gratifying beyond the financial rewards and ability to have a more flexible lifestyle for my family, but also because I can really take the time to help clients find the best solutions to their tax issues. Lifestyle-wise I can juggle my schedule to keep up with different activities such as managing our investments and fun activities for my three-year-old daughter, plus I have the flexibility of location for long holidays and supporting my husband’s career adventures. I’m actually nine months pregnant now and it is great to be able to relax at home, while still pumping out work. Downside, of course, is that I don’t get any paid leave whether for vacation or maternity, and it’s not just the financial aspects that are challenging for that, as I have to be available to answer emails and urgent questions even when taking down-time.
Honestly, the most unexpected challenge was how hard it is to keep up with all the paperwork and regulations for my own company. This is a little ironic, considering I own a tax firm. Especially state taxes are complicated and tough to comply with. Even for someone such as myself who understands tax law at a high level, it can be daunting at times to be operating in several states and keeping track of the ever-changing regulations. Seems so much more challenging with my own company somehow, and it really makes me compassionate when I have clients who are confused about a business tax issue. Grateful that I can be there to help them comply with regulations and hopefully I am able to take some of the fear out of the process along the way.”