Fear, urgency, and figuring it out one day at a time

Do you have life all figured out?

I don’t, and I’m slowly realizing that that’s OK.

Last spring I left a comfortable job at a venture capital firm to head back to an early-stage tech startup. I missed the “hustle” and startup culture, plus I wanted to make more of a direct impact. I identified a company that I thought was right up my alley, reached out cold, and after a couple months of discussions, they offered me the exact role I wanted at the exact salary I wanted.

I was ecstatic.

Leading up to my start date, all my friends and family heard about was how the “stars had aligned” and how I had finally found my “dream job”.

Welp…..I think we all know where this is headed. Within a few weeks (yes, weeks) of starting, I knew it wasn’t going to be a long-term fit. And of course my boss did too. At the five month mark, we parted ways.

During the final couple of months I went through all the various stages of job mourning — feeling crushed and disappointed, angry at myself for not being able to make it work, exhausted at the thought of beginning the job search again, and finally accepting that it would soon be time to move on. I forced myself to begin networking and exploring new opportunities.

Like many entrepreneurs, I keep that little black book on my night stand for when an idea strikes. Over the years, since CitySwarm (my first company, an event marketing business), I’ve collected dozens of ideas, quietly waiting in the wings for their time to shine. But when something fails — a new job, a business, a relationship — your confidence inevitably takes a hit. At this point, starting a new business seemed like a horrible option and, frankly, impossible.

But as I continued to meet with friends and colleagues, many of whom are entrepreneurs themselves, the exhaustion and hopelessness slowly changed to excitement. Hearing their stories of overcoming obstacles and creating companies out of nothing reminded me that “I’d done it before, I could do it again”. With my newfound excitement, I made the choice to step back into entrepreneurship.

Here’s where it gets tricky.

When I started CitySwarm in 2010, the idea had been burning a hole in my mind for months — maybe years. This time around, I didn’t have just one idea…..I had about 20. I went back and forth daily but was unable to land on one. So, I scheduled a “business meeting” with my dad and brother with the goal of hashing out the ideas and choosing one to move forward with.

This started out as a super fun task. I enjoy getting feedback on business ideas and took vigorous notes as we analyzed each concept at my parents’ kitchen table. But somewhere around idea four or five, I felt the excitement transitioning — into fear, anxiety, and borderline nausea.

By the time I got to my therapist’s office the next day (yes, I see a therapist), I was in complete panic mode, overwhelmed and in tears.

I told her about how I was trying to pick a business idea but couldn’t decide on one. How choosing a business to launch felt like so much pressure and so daunting, because I didn’t want to choose the wrong one and waste my time or embarrass myself (and wind up in a van down by the river….). How I HAD to pick an idea ASAP so that I could continue #adulting and pay my newly-acquired mortgage.

She suggested we tackle one issue at a time and asked, “Is there anything you can do to stabilize yourself financially while also giving yourself time to work on your business ideas?”

She’s such a smart cookie. I thought for a minute, then hesitantly explained that I’d always been curious about the world of “consulting”. Like….what exactly do consultants do? Could I be one? I knew people who had done it, and I feel like they were normal people just like me…

And so, that was the game plan I decided on, and my consulting practice was born.

I committed to giving myself a *minimum* of six months to get the consulting practice up and running (i.e. make enough money to live relatively comfortably without needing to cancel all social plans and sell all belongings). I also listed my second bedroom on AirBnB to earn extra cash in the meantime.

Almost immediately I was able to land two clients*. I had grand plans of a big launch to family and friends, but kept putting it off week after week. Month three rolled around, and I hadn’t done much in the way of promoting my business (which was the purpose of this first six months). When I finally pushed myself to make progress and start nailing down details of a name and logo, the fear crept back in. One question led to the next, and I second-guessed myself down a fear-spiral.

I don’t know about this name anymore…what if people think it’s stupid?

I haven’t made any progress on my business ideas. Wasn’t that the whole point of consulting to begin with?

Do I even like being a consultant? Should I just scrap this whole thing and get a job?

How could I possibly “launch” a consulting company if I’m just going to get a job in six weeks? I’ll look so dumb!

I was stopping myself before I even got started. I felt the clouds rolling in and quickly reached back out to my support system — friends, family, and of course, my therapist — for help. We talked about my paralyzing fears — of embarrassment, failure, wasting time — all of which stopped me from moving forward with anything. But in procrastinating, wasn’t I putting myself through most of things I was hoping to avoid?

Two things happened next that made me bounce back.

First, I promised myself that the next day I’d tackle something I’d been putting off for weeks — sending an email to five business contacts letting them know I was consulting for startups. I completed this small task, and it felt great. A few days later I had coffee with one of these contacts, and that meeting led to an ongoing engagement of 15 hours/week. I finally felt like I could breathe. The plan was to dedicate half my time to my new project, and half my time to the startup ideas.

Then, I met a friend for brunch on yet another bitter cold December day. She was irritated that her dog, who was used to hours of frisbee in the park, would only go out for moments at a time due to the cold. His pent-up energy was getting him into mischief around the house. I suggested she take him to an indoor dog park, and when she said she didn’t really know of any, the lightbulb went off — an indoor dog park pop-up (aka “pup-up”…..cuz who doesn’t love a dog pun?).

With winter in Chicago being already half over, I knew I needed to start working on this idea ASAP. I jumped into research mode and spent all my free time working on this idea, emailing commercial real estate brokers, putting together projected budgets, and researching animal care license guidelines.

Then it dawned on me…

I had spent MONTHS procrastinating getting ANY of my ideas off the ground, and yet I made significant progress on this idea in a matter of days.

It was the urgency. The girl who wrote papers weeks in advance of the due date was long gone. I needed deadlines, and the fact that the idea was time-sensitive (hello SMART goals) gave me the exact kick in the pants I needed to get moving.

After this realization, I thought about my long list of ideas, and an idea ABOUT the ideas popped into my head. What if……….I tried to launch one of my ideas each month for 12 months? While this seemed kind of crazy, it also seemed like the perfect way to exercise my creativity and replicate the sense of urgency without experiencing the crippling pressure of picking “the one”.

Yet again, the time sensitivity of the project made me jump into research mode immediately. I Googled to see if anyone else had ever done this, and sure enough, I found three comrades — Peter Levels (levels.io) and Elijah Murray, who both did the “12 businesses in 12 months” challenge (their stories here and here, respectively), and Ryan Robinson, who challenged himself to validate and launch a business in 30 days prove to his following it could be done.

I excitedly read their blogs and reached out to see if they’d be willing to provide some insight into their experiences (and whether or not they’d recommend it). Elijah and Ryan both wrote back quickly and we scheduled times to chat.

And that brings us to this entrepreneurial experiment.

I’m calling it The #Bizamo Project (shortened from “Business a Month”).  I don’t know where this will lead or what the outcome will be, but I’m learning to embrace the uncomfortable and trust that it will figure itself out. Two things I AM certain of: I’ll learn a lot and meet cool people along the way, and I’m feeling SO much happier now that I have a plan in place that allows me the freedom to explore my ideas.

I’d love to hear your thoughts. Have you experienced something similar? Are you trying to “figure it out” amongst a sea of people who seemingly have it all together? Feel free to leave a comment below or email me at lindsay@bizamo.co. 

If you want to follow me on this journey of the unknown, you can subscribe to my email list or check out bizamo.co to see each new business get launched (first one – Whoopla – went up last week!). 


A version of this post first appeared on Medium.

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