Why Am I Doing This? 5 Questions Creatives Should Be Asking Themselves

In the midst of the holidays, it’s easy to become wistful about one’s creative lifestyle: many begin to wonder what it would be like to have a “normal” life, where they could be spending time with friends and loved ones instead of working. And others who are able to take time off may find it difficult to navigate getting back to work when there’s no one telling them to do so.

While this time of year is often filled with fun and joy, it can also be a time of questioning one’s career choices.

And it should be. In fact, creatives should ask themselves these questions frequently. Things change over time, and if we aren’t checking in with ourselves, we might find ourselves going around in circles rather that really moving forward. Here are some questions every creative should be asking – at least once a year.

1. Why am I doing this?

I notice people asking themselves this a lot, but unfortunately it’s usually during a state of frustration and feeling hopeless rather than truly answering the question for what it is. The time to ask yourself this is not in moments when you’re experiencing highs or lows, but when you can look at the reasoning objectively.

When you answer this question, dig deep. Answers like, “I love what I do!” are not enough to keep you going when times are tough. There have to be some major pros to offset the sacrifices, frustrations, and disappointments along the way. If you don’t have a deep-seeded, rational reasoning for putting yourself out there time and again, it’s easy to feel like you’ve lost your purpose.

2. What do/don’t I like about this work?

Again, be objective and thorough. Think about ALL aspects of your work and business, and make two lists – things you like about it and things you don’t like about it. Everyone can make these lists about any job; we all have things we like and don’t like about what we do. And it’s different for each person – one person might love the travel aspect of their job and one person might hate that part. So these aren’t lists to be compared with anyone else’s. Be honest rather than writing what you think you should like as opposed to what you really do enjoy. This can be a real eye opener.

3. What do I need in my life to be happy?

This is an interesting question, and ignoring it could mean that you’re missing out on your true calling! Think about all aspects of your life: family, friends, significant others, pets, other activities you enjoy, home life, work, finances, work schedule, etc. Is what you’re doing truly feeding what makes you happy? If not, what’s the point? You may find that you need to make some adjustments, or maybe you’re not even doing what makes you happy. Note that I’m not saying you can “have it all” – there will always be sacrifices, and there are usually difficulties that go along with doing something we love. But if you’re typically in a perpetual state of unhappiness, something needs to change.

4. Am I capable of being my own boss?

It’s unfortunate that our educational system doesn’t teach people that their creative skill is step zero when it comes to being successful at using that skill to make a living. Instead, you’re told things like, “If you work hard and you’re talented enough, you’ll make it!” and “Just find what you love and do that for a living!”

That sounds great, but there’s a giant chasm of information missing from statements like these. I’d propose something more like this: “If you have a talent for which you don’t mind being judged, and you have a desire to cultivate business and management skills, and you’re willing to make sacrifices in order to pursue using your talent to attempt to make a living, and you’re really ok with failure, then maybe a career as a creative entrepreneur is for you!”

Because that’s what every person who decides to work for themselves is – a creative entrepreneur. Do you remember entrepreneur courses being part of your degree curriculum if you went to school for your creative skill? Probably not. At best, you might have taken one quasi-business course unless you ventured out on your own to do so. If you ask me, everyone who decides to major in a creative skill should also have to minor in business. You need to understand finance and accounting, strategy, marketing, relationship networking, organization, enterprise, and operations.

You also have to be able to schedule yourself and be highly self-disciplined when it comes to work time. For the most part, it’s easy when you’re in school or in a production/project, because much of the schedule and pace is set for you. But when that’s not the case, most people find it difficult to be consistently productive without some sort of regimen, and it becomes even more difficult if you’re working another job.

Being your own boss sounds great, and it can be, but it’s not for everyone. You have to be able to be the one in charge as well as being the subordinate. You have to be willing to make tough decisions, and there’s rarely room for “I don’t feel like it.”

5. Am I resilient?

Almost every entrepreneurial success comes with stories of failure and people who were told they weren’t good enough or would never make it. And yet there they are, doing quite well.

Every once in a while you might run into someone who had an easy path, but that is a rarity, and so resilience is essential.

When the going gets tough, do you decide to get tougher? When you fail at something, do you see that as an opportunity to grow and improve? When you fall short, do you regroup and come back stronger?

If your reaction to failure and disappointment typically entails an immediate self-loathing pattern, filled with negativity and self-doubt, creative entrepreneurship is going to be difficult for you. I’m not saying you shouldn’t honor feelings of disappointment when things don’t go your way, but if those feelings lead to constant spirals of depression and not wanting to figure out how to get better and try again, I can imagine it would be quite difficult to reason with yourself as to why you want to continue such a pattern.

The good news: you can modify these behaviors if you wish. It’s hard work, but it is doable. And if you love what you do enough, it will be worth it to invest in changing your behavioral patterns so you don’t feel defeated when things don’t go as expected (which happens a lot).

Take some time and have a little Q & A session with yourself. The answers can be invaluable when it comes to ensuring that you’re moving in the right direction. And what’s right is up to you. 🙂

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