Do you have deadlines? Or do you have ‘creative checkpoints’?

I have a love and hate relationship with deadlines. I love it when I make my own. I hate it when they are handed down to me (with completely unrealistic expectations for completion). But, on the other hand, I love getting deadlines from other people. It makes me want to prove myself. I have a goal and an objective that forces me to make things happen. Because if I’m honest with myself, I know how making my own deadlines can go: I get lax. I put things off. I don’t have anyone holding me accountable but me.

Such is the struggle.

Since I started writing books, I never gave deadlines much thought. I could always work at my own pace. Nobody was looking over my shoulder. Yet as I began to release more stories and I saw people reading them, the pressure began to mount.

How soon can I get the next one out? 

If I don’t finish this next project by the end of next month, will I lose the interest of my readers? 

Should I move on to something else? 

A lot of questions began to circulate; the majority of which revolved around uncertainty. And where uncertainly festers, so does anxiety. It didn’t take long for me to realize that if I worked at a pace dictated by my audience, then I was going to sink fast. I would never be able to keep up and the quality of my work would diminish. So instead of trying to create unrealistic deadlines for myself, I decided I needed to work smarter, not with a sense of fear. I needed to make checkpoints, not hard stops. I needed to give myself space to breathe; not suffocate.

As much as creatives want no borders – no barriers to their creative impulses – it is of the utmost importance that we structure ourselves around a schedule. In that way, we can allow for our creativity to flow, not constrict.

For more on that, I’ll be discussing in my latest episode: “Do you have deadlines? Or do you have creative checkpoints?” 

 

“I was more invested in the process; not the product itself.” – Daniel Luketic, entrepreneur

A lot goes into getting an idea off the ground. Careful planning. Risk-taking. Gathering one’s resources. Creative endeavors are never small undertakings. And though one may think intangibles like divine inspiration or sheer determination separate the winners from the losers – there’s another trait I’d argue to be equally important: the willingness to fail.

When I interviewed my (former) college roommate, Daniel, we agreed beforehand that our main topic of conversation would be his first business venture. After graduation, I ran off into the insurance world while he got busy working for a startup. And while I was loathing my existence – drowning in insurance policies – Daniel was building technology for insurance agencies. A project which culminated with him selling the business off.

Sounds like not a happy ending. Or, rather, perhaps a failed one. But, Daniel had a different perspective.

I wasn’t interested in the product necessarily. I was more interested in the process. Learning how to troubleshoot. Learning to come up with solutions. 

I wanted to ask Daniel, why insurance? Aren’t there more lucrative and exciting industries to get involved in? That wasn’t the point though. In fact, the point wasn’t about insurance – it was about building a skill set and cultivating one’s strengths.

This was my greatest takeaway from interviewing my one-time bunk-bed-buddy. Yes, one ought to find a niche. But, we ought to be just as invested in learning how to build better work habits, i.e. troubleshooting, presenting solutions and then actually carrying out. How many times have you been in a workplace where nothing happens until something bad happens? I’ve been in those environments. They aren’t fun. And they don’t grow either. Personally or on the macro level.

Yet, by taking the vantage point of: what am I willing to learn from this experience? Then we’ve already put ourselves miles ahead of our competition. But, we must be willing to put ourselves out there. Make mistakes. Then keep going.

If you’d like to forego our smiling faces and listen to the audio-only version of the interview, you can check it out here.