How do you know when you should keep going versus when it makes sense to cut your losses and try something new? It’s a difficult decision most entrepreneurs and creatives have faced along their journey and so we asked some brilliant folks from the community to share their thoughts.

Sari De | Leadership Coach for people of color, and DEI consultant for companies creating more equitable systems.

Part of an entrepreneurial mindset (for me personally) is to not consider giving up an option. As a trained negotiator, one of the things I know is that you have to believe there’s an outcome that’s beneficial to all parties. Only when you believe that do you start to look for solutions that will give you that outcome. I translate that to my work, where if giving up is not an option and I have to keep moving forward, then the only options are “how do I solve this problem?”. Read more>>

Tyrone DuBose | America’s Premier R&B Historian

As a teenager, when I saw the movie Rocky, it made a tremendous impact on my life. I saw someone who had absolutely nothing to lose with a life that was 1 million to one shot lose a fight but show courage and strength. There are times in everyone’s life when they feel that way. I made up my mind however that I was going to do everything I could to make my dream come true. As we get later in our years, we recognize that this may very well be the last chance that we have an opportunity to make it happen. So no matter what I may feel, quitting or giving up has never been an option. We should always speak what we want. If you have a propensity to speak about how bad things are, it’s usually going in that direction. I’ve made up my mind that I will do everything that it takes to make my dreams come true. If you are one of those people who believe that you’re not sure, that means that you’re getting closer to making it happen. I’ve learned to never deny myself an opportunity to be at my best. Even when no one around me sees it, I must see it for myself. Read more>>

Jina Kim | YouTube blogger, Business Owner, and Real Estate investor

I’ve grown up giving up alot of things. To name a few: gymnastics, golf, guitar, clarinet, track, volleyball, basketball, architecture club, but all of these hobbies were things that I felt influenced to do. I never knew who I was or what I wanted. I remember always being envious of my creative friends and thinking how I wished I had something that I loved the way they did. It wasn’t until I lost my job at the age of 27 that I felt like I needed to figure myself out. I moved to LA and I had no choice but to find any job to make ends meet. I spent day after day applying and was looking for any opportunity. After a while, I realized that I needed to switch my mentality and really figure out what I wanted to do. I always wanted to start a business and I always had a love for food, so I went for it and started a cheesecake company that gradually turned into something so much bigger; Cheesecake Baos! It all started in November 2020. Read more>>

Keri Rosebraugh | Visual Artist

When I begin a project I approach it with some idea of what I am trying to convey – conceptually as well as aesthetically. Many times the hardest part is the beginning: putting paint to a white canvas or that first chisel into wood. It takes time for me to develop a relationship with the piece. The more I put into it, the more this prompts a dialogue between the work and myself and eventually the best part is when the piece starts telling me what to do next. I don’t really stop until the elements in the piece are cohesive (I hope) and I feel like the communication between the piece and myself is resolved. In answering this question in general, I just keep going. I mean even if someone gives up on something, another thing eventually pops up and then you’re off to the races again, right?. Read more>>

Morgan Taylor Jones | Singer, Songwriter, and Model

There have been many times within my career that I’ve thought about giving up. Pursuing a career as an artist is not an easy one. There’s no roadmap nor blueprint, and often no exact footsteps to follow. However, so many things continuously happen both to me and for me, each reminding me to never give up. First, the thoughts music and singing consistently swim around in my head, day in and day out. I think in song. I hear in harmony. And am always imagining myself performing. Next, whenever I’ve tried to deviate from this path, nothing comes close to fulfilling me and fueling me the way music does. Thirdly, the support I receive from friends, family, strangers, and many others also encourages me to keep going. Any time someone says they enjoy my song or that the lyrics I wrote resonated with them in some way, I know I’m on the right track and am supposed to keep going. Read more>>

Varun Sharma | Hip Hop Music Producer

1. If you quite what else are you gonna do? You started it for a reason. People think its supposed to be smooth sailing throughout the whole process. 2. If its not your passion or interest in general you failed way before you knew it imo. Read more>>

Kennedy Lindsay | Artist

When it comes to making and creating artwork I’ve learned that a piece or project is done when you first think you’re done but more ideas keep coming, I’ve ruined pieces by listening to those impulses, I think most work tells you what it needs you just have to listen to it and not to yourself.
But the harder question is how do you know when to give up pursuing a career in art? And I don’t know if I know the answer to that, I’ve been making work and trying to sell it my whole life, this is all I’ve ever wanted and the last year or so I’ve reconsidered a million times if this is what I want.
its hard to be an artist, there’s an eternal struggle between making work that people love and making work that you love, the two don’t always coincide, monetizing your creativity and passion isn’t as easy as it sounds. We live in a world that needs and wants art but never wants to pay for it. And its hard to figure out how to profit off your work to begin with, as its not something anyone can teach you, I went to college for art, and there isn’t much modern advice about how to make a career out of your creativity. Read more>>

NSTASIA | Artist

I have a friend that said this particular saying a long time ago that stuck with me for years. “Those who never give up, never not make it”.. Basically, the only way you won’t accomplish your dreams is if you give up. If you never give up then your success is inevitable. For years its been one of the main pieces of wisdom I’ve received that has kept me encouraged. If you really think about anyone who ended up not accomplishing their dreams , somewhere in there is a story about them giving up, for whatever the reason may be. We all go through moments of doubts, but this saying keeps me motivated. I believe whatever your desires are is what you should strive for. You desire it because its for you and you should go get it. Read more>>

Natasha Rudenko | Visual artist and educator

Know your heart. If deep down you know that’s not your real dream anymore – give up, if it is though – keep going. Back in Russia we used to jokingly say if you can’t run towards your dream – walk towards it, if you can’t walk – crawl, if can’t crawl – lay down in the direction of your dream. Jokes aside, when I feel down and stuck I imagine myself in a desert laying down on my stomach looking at the distant foggy mountains glowing in the setting red-orange sun in front of me and I think to myself: I’m just tired, I still head in the right direction, I see the light, I’ll continue in the morning – and it helps. Read more>>

Kimmy Burns | Artist

I’ve always had the “keep going” mentality. If you decide to give up, whether it be on your hopes and dreams, career, relationships, you’ll never know if that level up was only right around the corner. The possibility that my situation can change at any time is what keeps me going and keeps me pursuing my art. A bit of a thrill if you ask me. I’ve had so many great experiences and opportunities already that I wouldn’t have if I had decided to give up when things seemed stagnant or impossible. I’ve had to pick myself up more times than I can count, and my advice is to brush yourself off because that could be the fall right before the fortune. Read more>>

Alan Fleming | Videographer & cinematography

With regards to videography, this felt like a very organic process. A lot of hard work, long days and nights. But I don’t believe I ever felt like when things were slow or hard for me that I needed to give up. I’m not sure if I know how to throw in the towel. Read more>>

Leslie Henry | CEO

First, you have to be honest with yourself about why you started. What exactly is your why? Is this something that you enjoy doing or are you in it just to make money. Once you answer those questions honestly then you will know whether or not you should give up. I personally feel like giving up is not an option because you will always run into hard times. If you remember your ‘why’ you will always find it in you to keep pushing and figure out ways to make it work. Nothing comes easy and you have to go hard in order for you and your brand to get to the next level. However, if you answered those questions and the answer is only money generated then maybe you just have to find something that is important to you. If its something that you really want, you will get it done no. Read more>>

Kim Hayashi | Leadership Development Consultant

I feel like just saying, “it’s complicated”. I have a million ideas and have to always stop myself and focus – which means I “give up” on things ALL the time. There are other times when I think it would be so much easier to be an employee – to not have the responsibility of others or an organization. You never know what the right decision is, you just have to find what drives you and use it to guide you. I continually use our vision of “inspiring learning, leadership, and service” as a guidepost – and remind myself of the positive work that we are doing. We have been so fortunate to have so many wonderful clients provide testimonials and I know I can always refer to them to motivate me to keep going. To sum it all up, I still have a strong drive to accomplish, and until that fire goes out, “giving up” will always just be a way of saying “coming soon”. Read more>>

Lacey Caroline | Award-winning actress, kid reporter and host

This is a really relevant question for actors as there are many times along the way when you may feel that your best just isn’t good enough…when you are one of the top 2 choices for a role, and you don’t get cast or when you go through callbacks, producer sessions, chemistry reads and you just aren’t quite right. But the love of acting and working with a cast and crew is what keeps me going! I feel so lucky to have come this far and know that a big role is right around the corner. Read more>>

Alvin de Castro | Choreographer, Dancer & Educator

I think the term “give up” has a negative connotation so I like to think of it as “moving on” or graduating onto something different, if not better. In context of professional life, I think that the most important thing to realise is that a career is a living, breathing thing and it will change as we change. And thats OK! If you’re no longer growing, learning, or enjoying what you do, it’s not healthy to box yourself in and limit your possibilities. You can either try to find new ways to be happy again or simply take what experience you’ve gained and sow that into other areas so that you can thrive. I did this when I left my graphic design position to become a full-time choreographer. You’d be surprised how much of your existing design skills can be utilised in other creative roles – such as in dance!. Read more>>

Christina Bulbenko Rex Broome | The Armoires, indie pop band

Christina: We’re a band, but Rex and I also run Big Stir Records, and in pre-pandemic times we produced a lot of live shows for bands on the guitar pop scene. The onset of the pandemic obviously posed a lot of challenges to both of those enterprises. On the label side, we were responsible for the work and livelihood of a whole bunch of artists who were about to get hit hard by the changes in the world. We felt like we couldn’t give up on that, and we resolved to to keep going and get better at what we do for them. Rex: In fact we were grateful to be busy and have challenges to meet. That was better than doing nothing, and it had meaning. But for ourselves as a band, we really didn’t think much about it at first. We are typically a very busy live group, we need all of our members to do recordings, and we didn’t foresee ourselves being able to make a record under quarantine conditions. Read more>>

Hayden Allcorn | Comedy Magician and Actor

As artists, creatives, and humans, we are always met with the struggle of taking the easy route and either giving up or moving on. However as artists, creatives, and humans, we have been tasked with the incredible gift of story telling. For as long as I can remember, I have given myself the daily creed to “invite at least one person every day to laugh or smile” because that is something I can offer to the world. While I may not be able to cure disease, build machinery to help communities, or donate endlessly to those who have less, what I can offer is the moment of laughter or sheer happiness. When we laugh or smile, even if for just a moment, we forget the nastiness and frustration in the world around us, and we just get to be present in the moment. As a comedy magician, I am nothing more than a story teller with unique props to help tell that story. Read more>>

Brandon Miree | Storyteller for Screen

“Don’t give up what you want most for what you want at the moment.” In the triple-digit Alabama heat, where the sun seemed like it was sitting 10-feet above you, those words would echo through the earholes of our helmets. Usually, at times we didn’t want to hear it while running sprints in full football gear. The sprints were aptly named, ‘gassers,’ where we’d run the width of the football field (53 yards) and back TWICE for one full-gasser. We had to execute this under a specified time, at the mercy of a stopwatch that allowed for 40-second breaks. Gassers made otherwise strong and healthy young men into pouty kids or temporary medical patients. Guys would lay prostrate on the ground, hurl last night’s meals into garbage cans or cuss at the sun. We were college football players at the University of Alabama, where EVERY year the goal was a national championship. Read more>>

Vincethealien | Singer/Songwriter, Recording Artist, Podcaster & Author

As an artist, I have found myself at times afraid to wrestle with those feelings and inner voices that say give up. This journey is not easy; it can feel long and, at times, come with a lot of output with little reward and more no than yes. I’ve had many moments so far where I have felt like letting go and giving up on this dream I’ve had since I was that little kid in my room, closing my eyes and imagining being the superstar I knew I had the potential to become. As an adult, I’ve had to face the reality that those childhood dreams haven’t turned out to look exactly like they did when I was a little alien and that hasn’t always been easy to accept, yet remembering the excitement that still lives and breathes in me whenever I create a new song or body of work is the reminder that I can keep going. In addition, recognizing when it’s time to create and when it’s time to step back and allow myself the time to recharge has been key in me not giving up on myself as well. Read more>>

Christine Apostolina Beirne | Artist

How can I give up? After many years, I’m getting comfortable with my skills, with my “voice”: giving up is not an option. If I gave up, I would’ve wasted the last 25+ years. Read more>>

Samantha Kour | Wedding & Elopement Photographer

In the life of an entrepreneur, your livelihood is your business. Your success, your wellbeing, your income – it all relies on you. There are days where you don’t want to do a single thing, and as your own boss it can be hard to put your foot down and get to work. But when it’s necessary, you HAVE to be willing to put in the effort. Within the past year, we’ve seen thousands of businesses close down because of regulations and a huge loss of their revenue. While it’s been tough for so many, businesses have to be able to withstand the dark times. Getting through to the other side during something like the pandemic is proof to never give up – when life changes, keep adapting to new technologies, new ways of marketing, meet people at where they’re at vs. where you want them to be. And maybe none of it works. That’s okay, too. if you have a safety net to get you by in the meantime, it could be beneficial to take a break and revisit something new. Read more>>

Regina Valmadrid | Theater and Film Actor

Art can be made out of the effects of continuing your pursuit or giving it up so, the pressure of change should not be as feared as we make it out to be. In my opinion, driven passion is what makes my gut speak so loudly to keep going. If I am not feeling creatively propelling and desperately needing to reach new bounds, then I know that I should give up. And, that idea should no longer have a negative connotation strung to it. It is not just a bad day, an unproductive month, or a needed break, it is an absence of care and emptyness of interest. Personally, I have a hard time living my artistic and non-artistic life 100% honestly but what I have come to realize is that, caring, at its core, is simply just being truthful. If I am selfish and dishonest to my myself or my art then my creativity is killed and no one will see the true depths it could have been. Read more>>

Jess Kaplan | YouTuber/Fitness Enthusiast/Activewear Addict

I find it very difficult to give up on anything. When I was a kid my parents taught me to see everything through til the end. In third grade I played softball and my team was last in the whole entire town. I played right field, which means the ball rarely came my way. I never swung at bat because I knew the pitchers weren’t all that good and would usually just walk me. You might say that’s giving up, but I call it strategic. I didn’t like playing softball and I desperately wanted to quit, but my mom would not allow it. She said I would be letting the team down, and that they couldn’t play without me. Personally I think they would have been better off without me, but who knows. I think back to my jobs- 3 years as a newspaper carrier, 4 years at the children’s retailer The Rugged Bear, 9 years at J.Crew, 15 years at my current job. Once I begin something, I am extremely loyal.
It’s hard for me to give up. It takes a LOT! Albert Einstein said, “You never fail until you stop trying.” I believe in that wholeheartedly. Read more>>

Against The Sun | Modern Rock/Alt Metal Band

This band has existed for seven years. It started when our singer, Brad West, was in high school as a way to showcase some of the music he had written over the years. We have gone through several lineup changes over the years and our members had periods where other parts of their lives had to take over. For many of these years, we were kids. We didn’t know what we were doing, never thinking too far ahead. Still, we made a name for ourselves in the local scene, performing at Knotfest 2019, headlining Chain Reaction, and selling out the House of Blues in Anaheim. Then, of course, the pandemic happened. COVID-19 put everything on hold for us. If there was ever a time to tell ourselves that it wasn’t meant to be or that there was no opportunities for us to grow, this would have been the time. Instead, we did just the opposite. We focused on writing new material, perfecting the songs we already had, and we took a critical look at the way we ran our band. Read more>>

Tina Quach | Film Director

I feel the best way is to determine to keep going or give up is to constantly question: “What is my main, long-term goal?” Sometimes within the moment, it’s hard to picture life as chapters of a book where we may hold on to certain things, certain jobs, or certain people longer than we should. I feel it’s best to question how these factors are serving us at the moment for that goal. Note that goals can change too and that’s okay. Within my journey, my initial goal was to work in Film and Television which I achieved very quickly; however, what I discovered that was more fulfilling was to create genuine connections with people, whether it’s through conversation or through the medium of film. It took me a while to realize that goal and noticed there were many moments I should’ve given up and redirected my energy. There’s only so much someone or a situation can give and understanding that will help determine to hold on or give up. There shouldn’t be shame of “giving up”. The reality is the only option really is “keep going”; it’s just the matter of how you want to keep going. Read more>>

Courtney Alexander | Personal Trainer & Health Coach

I think it comes down to three questions, really: 1) is the effort worth the reward? 2) why are you working toward this goal? 3) are you satisfied with your effort? Most of us have had the experience of trying something and failing, trying again and failing again. I think there comes a time when you’ve tried to achieve something enough times and failed that you start to ask yourself if it’s worth it, which is natural because we only have so much energy, time, and other resources to put into a task. The time spent working toward this goal might not be worth the financial hardship, the time away from family, the fatigue, etc., but if you’ve decided that it is indeed worth it, then move on to question number 2. Read more>>

Shohreh Khalilova | Designer, writer, and film producer

If you want to be successful at something, giving up is not an option. Success becomes the only option. That means, when things get tough, hardships continue to rise, and you feel uninspired, you remind yourself that it’s part of the process in order to achieve your goals. I like to reference the Hubble Telescope. The astronauts that worked on it in space had to focus on one bolt at a time. The stakes were high, gravity wasn’t present, and one mistake could sabotage the entire mission. What lead to their successful accomplishments was not allowing themselves to be overwhelmed by what may be ahead, rather, it was the ability to focus on screwing in one bolt at a time. Read more>>

Kim McVicar  | Stand Up Comedian

For me when it comes to goals, it’s a simple weigh your pros and cons. If it brings you joy keep going, but if in doing so it hurts others – meaning you can’t pay your bills, you can’t take care of your children, or whatever your personal circumstances are – then that’s when you really have to think about giving up. And maybe it’s not giving up forever, it’s just putting it on pause and refocusing your energy. Read more>>

Belle Adams | Actor & Artist

From an acting perspective: Check in with you. If it excites you, fulfills you, challenges you to grow, makes you feel connected to yourself and others, lights you up — Keep going. If it makes you doubt yourself, drains you, pushes your boundaries, doesn’t respect your values, damages your sense of self — get out of there or reevaluate the approach. It is hard, but it is worth it – unless it isn’t. Read more>>

Jessica Pappas | Owner – Jessica’s A List & Writer

In March 2020, like so many others, I had to close my business. But there’s blessings in the unknowingness of it all. At first I enjoyed the fact that all my responsibilities were put on hold. I could sit back and reflect on how I imagine my life when/if things get back to “normal.” As far as Jessica’s A List, I thought now is a good time to think of ways to make my business better. And, also a great time to do more of what I’ve always wanted to and have been fumbling around with for years, which is to write. When I opened my business fifteen years ago, my goal was to build a great brand in my field. And once I did it would allow me the freedom to write. I would be that cool chick who owns that cool business and wrote that great book or that brilliant movie. It is possible I was a bit idealistic, I suppose. It’s definitely not easy to do it all. Read more>>

Eliza Hayes Maher | Actor, Writer, Producer

I’ve asked myself this question approximately 239802938 times since I graduated from college. I’ve chosen a career in the entertainment industry – one that relies mostly on other people giving me the approval to do something that I know I’m good at – and much of my time is spent waiting on a “yes” that often doesn’t come. Even as I get older, and relatively more “successful” (whatever that means anymore) I’m not convinced that the question will ever fully go away. What I do know is that I have gotten better at talking myself down from the proverbial cliff’s edge when it pops into my head. I’ve learned that when we ask our selves: “should I just give up?” We’re usually being too extreme. We ought to ask ourselves questions like: do I need a break? Or, should I offer myself time and space away from this thing so that I can tend to my mental or physical health? Or, is this fun anymore? These questions take the dramatics out of the dialogue – they give us the steering wheel, and allow us to figure out what’s bringing us joy and what isn’t. Read more>>

GESHIE | Musician / Artist

There is a quote by James Baldwin that I adore and it says “ If it hurts you that’s not what is important. Everyone is hurt. What is important , what Bull whips you what corrals you what drives you what torments you is that you must find some way of using this to connect you with everyone else that is alive this is all you have to do it with you must understand that your pain is trivial except so far that you use it to connect with other peoples pain and if you can do that with your pain you can be released from it and then hopefully it works the other way around to”. Whenever I think of giving up I always think about this quote and how my life purpose is to be of service to others. One of those main services is sharing my pain, my joy, my life through art . Music is a conversation between pauses of silence and moments of awareness and through those pauses I try to be an open channel. That is how I know to keep going on by using every aspect of my life to be the driving force for beauty in someone else’s that is the only way I can create without limitations. Read more>>