On an unexceptional Tuesday in November, everything changed. 

The week started like any other that time of year. It was nearly the end of my first full year as a writer. Though the year started with the usual fervor and commitment to 87 unattainable goals, November arrived with only a handful of them met. Stepping into my office and flopping down into the chair, I tried to resist the mental pull of the spiral of overwhelm that inevitably ended in defeatism.

I started my computer, then pulled up Gmail and read through an email from the online writer’s community I joined two months prior. The subject read, “We’re starting a mastermind!” I received the email that weekend, but assumed it was something to do with their conference, which was happening that weekend, I decided it could wait until Monday. 

I opened it and felt the dormant thrill of excitement rekindle as I read through the email. Clicking on the button to learn more, I was whisked to a web page filled with details. I devoured the descriptions of monthly one-on-one coaching calls with the co-founders, all-cohort calls, weekly office hours, and three in-person gatherings. All focused on helping the cohort members make significant progress toward their writing goals in 2020.

Every word echoed a deeply felt need inside of me, missing links I’d been unable to complete on my own. I wanted someone to help me see what was possible for my work, someone who had been in my position or was currently in that position to run ideas by. I craved someone who might notice if I gave up on a project before it had time to take off. I wanted someone I felt entitled to ask for help and guidance. I didn’t need someone to do the work for me, just someone to challenge and encourage me in the way only another creative can.

As I reached the bottom of the page, I knew they were building up to the cost. With all they were offering, it had to be steep. I inhaled sharply as I saw both the price and the application deadline-that Saturday. 

Five days to make a monumental decision that would require significant monetary and emotional commitment? Would you also like my social security number while we’re at it? Could I trust these people to follow through on what they were offering? Would I allow myself and my work to be truly seen?

As much as I wanted to click the button to fill out the application and pay my non-refundable application fee, I worried I was getting swept up by my own desperation. I needed time and space to think. I tried to put the offer out of my mind as I thought about completing that week’s writing tasks, my upcoming podcast season, and the query letters I’d sent to literary agents. Each reminded me how deeply I wanted what the cohort offered, and that the current trajectory of toiling away on my own was not pointed toward success. I struggled through my immediate tasks before giving in and turning my attention to the mastermind. 

I mentally walked through my options and reflected on where my hesitation came from. Part of me logically deliberated the offer and potential ROI, then considered the business-y variables. But there was also the fearful, self-doubting voice that demanded its day in court. 

I was afraid that I wouldn’t be able to measure up to the challenge, that I wasn’t a good enough writer or marketer. I was afraid it was a bad investment. I was afraid that I’d get into this cohort only to find that I didn’t like working with the other masterminders. Cohorts are, I reasoned, dependent on the people in them

The next day, Tuesday, I fought to focus on the day’s tasks, but my brain drifted to the mastermind in my unguarded moments. That evening before shutting down my computer and leaving for the day, I said a tentative yes. I decided to apply. 

I can always decline, I reasoned, and who even says I’ll get in? Maybe I would be rejected-I’d get my application fee back and the decision would be made for me. I filled out the application as honestly as possible, put in my credit card info, and hit submit. 

Over the next week, I talked to five confidants: my therapist, my sister, and three friends. Two of those conversations happened on walks, and one perched atop a rock in Central Park. Each helped me move through the pros and cons, and asked what I wanted. They helped me see potential alternatives. 

But, in their wisdom, none of them told me what they thought I should do. None of them would make the decision for me. Even as I hashed and rehashed the variables, I realized I wasn’t just looking for advice. I was hoping to defer responsibility. 

Frustrated by the high quality of my friends, I sat quietly with God, asking for some guidance. I heard a quiet, It’s your decision. What should have been freeing was just maddening. If I couldn’t even cast responsibility on God, I didn’t have a fall guy if things went sideways. Rude. 

One week after submitting my application, I received an email from the co-founders. It took me to a webpage with a video. The first word uttered was my name, “MaaaaaryB!” They each said their lines, obviously scripted but with enough personal details to show they knew who I was and what I was about. They said yes to me. They wanted to help me. 

I knew they also wanted my money, but I started leaning toward trust when I heard them say my name. They didn’t call me “Mary,” as countless other professional acquaintances had in the past.

They made the effort to say the “B.” 

The information below the video stated that I had five days to indicate my acceptance by making my first payment, with the assurance that I could reach out with any questions. Over the course of those days, I privately pondered, and watched my acceptance video at least thrice daily. It was nice to feel wanted, but I was determined not to let it go to my head. 

The day of the deadline, I met a friend for brunch. It was Sunday and our neighborhood go-to spot overflowed with energy as we sat at a hightop table near the door. After catching up on her life and work situation, I burst out the practiced spiel of pros and cons. Each point ended with the same phrase: “I dunno, though.” 

She also did not tell me what I should do, but listened patiently and asked questions. I barely ate as I explained and gesticulated, fretting myself in circles. We paid and parted, me leaning toward saying no and creating an accountability structure of my own. 

I  went about my day wondering why I couldn’t just decide. It should have been straightforward. I wanted and needed accountability and guidance. I knew this could be a game changer for my creative work. And yet, the thought of investing that amount of money in something I wanted sent my brain into a tailspin with only one objective: talking me out of it. It wanted guarantees and assurances. It wanted to know beyond a shadow of a doubt that these people were trustworthy, that they were the ones I should ask for help. 

That night, with the deadline looming, I slumped onto my couch and grabbed my iPad. I opened the web browser to the saved page. I watched the video and nearly chose my payment plan. The familiar reel of questions and “should’s” started. But after ten bless-ed days of spinning my wheels and thinking myself into many-a tension headache, something released in me. 

Bottom-line, I wanted to do it. Maybe it was a mistake, maybe it would be the best decision I ever made. Even if by some happenstance the cohort was made up of garbage humans, the rest of the offerings were well worth the price. I realized that it’s always a gamble when humans are involved. And since I exhausted all avenues of objection and still wanted to go for it, I had my answer. 

I took a deep breath and clicked “Select my payment plan.” When the deed was done, a confirmation page popped up. Animated confetti rained down over the brief welcome message. I hoped to feel relief, thereby confirming that I’d made the right decision. It didn’t come. Excitement came, but clicking the button satiated none of my fears. There was so much I wouldn’t know until I was in it. 

I sat back on my couch. I said a big yes to my creative work, a yes that other people would hold me to when I inevitably questioned the decision and the work. I decided to gamble that these people could be my people. Whether that bet would pay off or not, I’d said yes to the step that seemed best given the information I had in spite of my insecurities. And for the moment, I reflected, that was victory enough.