BOBBY: My older brother is doing so well in business. My younger sister is graduating with honors, and I also have a stepsister who is a celebrated lawyer. When we get together, there is always something to celebrate — my brother’s latest business achievement, my sister’s academic awards, my stepsister’s career. I’m a struggling painter. I know there’s nothing wrong with what I do. I love painting, and I’m trying to make a living from it. But sometimes, during family gatherings, when everyone talks about careers and accomplishments, I find myself becoming quiet. I wonder what I can contribute to the conversation. And sometimes, I sense that my parents really do not see my work as a real career. They worry about my future. At what point does wanting to make my family proud become living a life that isn’t really mine?
DJ: I don’t think you have to choose between making your family proud and being true to yourself. But you do have to be honest about what you are trying to build.
Being a painter is a legitimate career. But loving what you do and being able to make a sustainable living from it are two different things. Your parents may not be questioning the value of your work. They may simply be worried about whether it can support you in the long run.
Look at the reality. How much do you need to earn each month to live independently? How much are you currently earning from painting? How many paintings or commissions do you need to sell to reach that? Is your income growing? Do you have regular clients or commissions? Are you actively marketing your work or simply waiting for people to discover you? Do you have a portfolio and social media presence? Are you active in exhibitions and galleries? Are you developing your skills and your network? Do you have a plan for making your income more sustainable?
If the answer is yes, then perhaps you need to give yourself permission to build your career at your own pace — and give your parents something concrete to see beyond the label of “struggling painter.”
But if the numbers aren’t working, don’t be afraid to acknowledge that either. You don’t have to abandon painting. But depending on your answers to those questions, you may need to find another source of income while you build your art career. A part-time job, freelance work, teaching art, commissioned work, commercial painting or another income stream could give you financial stability without requiring you to give up painting.
And when you sit with your family, you don’t have to arrive with an achievement to prove that you belong at the table. You are allowed to celebrate their success without turning it into evidence of your own inadequacy. Build your career based on the life you want to sustain, not the reaction you want to get at the next family gathering.
Different careers have different definitions of progress. It might be earning more, getting your first major exhibition, building a body of work, becoming financially independent or simply becoming more disciplined about your craft. You need your own scoreboard.
Give yourself a realistic timeframe. If the plan works, continue. If it doesn’t, adjust the strategy. Not necessarily by abandoning the dream. Struggling for a dream can be noble. Staying stuck without changing anything is not. Your job is to make sure your chosen path is actually taking you somewhere.
Let their achievements be theirs, and let your responsibility be to live with honesty, dignity and purpose. The most important success is not having the most impressive story to tell but having the courage to live a life that is truly your own.
