Asking Not Asking #25: Aiming to Avoid Regret
TINA ESSMAKER / Creative Coach
Hi Tina,
I’m trying to make a tough career decision and I need help. I have a good-paying job as a designer at a small, but growing startup, yet I’ve always had the dream to pursue a more independent path as an illustrator. I’ve dabbled in it in the past, but it’s never sustained me full-time.
I do have some options financially. I could move and have less overhead or I could get a roommate. I’ve thought about taking the next step, but I don’t know if it’s foolish when I make a good living that allows me to be independent and save. Is this a silly pipe dream?
Should I just let it go and do the reasonable and rational thing? Or should I try to be an illustrator? Sometimes I feel like it’s already too late, but I also don’t want to look back in 20 years and regret not trying.
Any insight you have to help me think this through would be appreciated.
Sincerely,
Avoiding Regret
Dear Avoiding Regret,
Regret is not logical or rational. So perhaps you can’t reason your way through this decision. Yes, logically it makes sense to keep on the path you’re walking. Keep the steady job that pays well, do the work, and save your money. That’s not a wrong route. But there is another option tugging at your heart.
How would you feel if you stayed the course and never pursued illustration as a career? Really think about the answer to that question. Think about your life in 10, 20, or 30 years. Will your future self be glad, relieved, happy? Or perhaps regretful, disappointed, and curious about what might have been?
Now think about how you’d feel if you pursued illustration and it worked out? Would you be thrilled, excited, pleased? Or maybe you’d feel anxious about the demands of that career. Perhaps you would decide it wasn’t such a great idea after all. But you will never know if it remains hypothetical.
Have you heard of the emotional balance sheet? Carl Richards writes about it in this New York Times article. Essentially, he asks us to reflect on our choices that are emotional assets. Making decisions based solely on mere dollars and cents may not give us the full equation. Many of the decisions we make and are happy we made are not wise financial decisions, he argues:
“I simply want us all to become aware of the need to write down our choices and assets even if they seem to defy calculation. Think of these items as lines on your emotional balance sheet... You could easily conclude that having children is always a bad financial decision and be right—mathematically. Except for the little issue of the value you place on having and raising a family. That value won’t fit neatly and numerically into any traditional asset or liability column, but it will fit on your emotional balance sheet.... If we limit our view to what can be measured in dollars, most of what brings us happiness could be defined as bad financial decisions. Travel, time with friends or long meals with parents could all qualify (or be disqualified, as the case may be), unless we’re also weighing the benefits that we can’t enter into a calculator. Real financial planning must acknowledge that reality.”
“Logic, mathematics, and budgets only paint part of the picture we need to consider as we make important decisions about our futures.”
Logic, mathematics, and budgets only paint part of the picture we need to consider as we make important decisions about our futures. It’s not wise to completely reject financial wisdom and throw caution to the wind, but it doesn’t seem like that’s your M.O. here. It appears as if you are considering the full weight of your decision on your finances, which is fairly straightforward. You make a sufficient salary now and transitioning into anything new will require that you build again and will likely make less to start. But could your earning potential be similar or higher? We don’t know that piece yet.
So, reflecting on the emotional balance sheet, what are the “assets” you might accrue in pursuing illustration as a viable path? Take a few minutes and list them out. Your list might include things like increased happiness, more confidence in your ability to reinvent, satisfaction in making your dream a reality. What are all of the non-financial assets you might gain? And how do those weigh against what you might sacrifice or give up, even if only for a season—a sense of security, some of your income, and so on?
This isn’t about choosing financial or emotional assets. It’s about finding a mix of both that works for you. Some of us can be extremely successful financially, but lack emotional fulfillment and feel disconnected from our work in a way that leads us to be restless and discontent. Some of us can be overflowing with emotional connection to our work, but we’re not making enough money, which makes it hard to sustain a quality of life that allows us to continue the work, or, frankly, we can’t pay the bills.
“We each get to determine what we need from our work to continue to do it. Right now, it sounds like you are doing well financially, but you need more than that. This is an opportunity to look within and uncover what that need is. ”
We all deserve to maintain a quality of life that meets our needs and fulfills our wants. And we all deserve to do work that has some kind of non-financial return, if that’s what we want. For some, work is a means to pay bills and support a family, but one may also find satisfaction in the pride of doing that. What I’m saying is that we each get to determine what we need from our work to continue to do it. Right now, it sounds like you are doing well financially, but you need more than that. This is an opportunity to look within and uncover what that need is.
I’ve been thinking often about ease versus resistance as of late. Not in the way of thinking that all of life and work should be easy—I don’t think that’s reality. But in the sense that we can go where the energy is. We can accept the ease that certain paths give us. There is nothing wrong with ease. There is also nothing wrong with experiencing confusion, heartbreak, challenges, and setbacks. All are part of life. But as someone who grew up in a blue-collar community in the Midwest, I saw struggle and adversity in the everyday. Because of that experience, I was ingrained with a sense that I was destined to work hard, struggle, and just get by.
What I am trying to say is that you are assuming that a new path will be hard. It might be a struggle, yes, but it may also feel like coming home to a place that has always existed for you. It is not too late for you yet. But at some point, it will be. You will have invested too much into your current life and the burden of making a change will feel too great. It will never become easier to make this decision.
“It is not too late for you yet. But at some point, it will be. You will have invested too much into your current life and the burden of making a change will feel too great. It will never become easier to make this decision.”
But you can lean into the ease you find in your life. By that I mean the things you are drawn to, the things you enjoy, like illustration. What would happen if you began to develop an illustration practice, giving yourself assignments? Then you would create a portfolio. What if you had work to show and told people you were available for hire? Then you would get clients. What if you could cultivate this new path step by step while maintaining some consistency with the income from your current job until the tension was too much and you had to choose? Then you would reduce some of the risk inherent with taking the leap without a safety net.
I don’t think you have to choose between your current job and an illustration career right now. I do think, however, that you must choose what is important to you. What goes on your asset list, both financial and emotional? What do you need to add up to a life fulfilled? It is impossible to have zero regrets, but we can hope that the regrets that surface as we reflect on the whole of our lives are on the smaller side. Deferred dreams are not a small regret. We can hope that overall we have spent our lives well and filled them with the things we most want, which are rarely a result of logic and rationale.
Regardless of the path you choose, I hope you look back and are glad you did. Now, keep moving.
To a well-lived life,
Coach Tina
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Asking Not Asking is a bi-monthly column written by Tina Essmaker, a New York City-based coach, speaker, and writer who helps others live into their possibility. To be considered for the column, send and email to tina@workingnotworking.com with a short note about where you're at and where you want to be, and make sure to include the following:
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