Soft Skills: The Secret to Being a Tired but Unstoppable Entrepreneur

entrepreneurship resilience adaptability soft skills

This article was originally published on Dec 9, 2021 on Medium here:

Resilience and Grit are Essential Soft Skills for Entrepreneurs

There are only a handful of blog posts and articles with founders talking openly about being tired and how the grind is wearing them down. Understandably, being vulnerable is hard for most people — doing so publicly as a founder gearing up for a fundraising round is downright risky and pretty much unheard of. What others choose to do is up to them, but I share how I feel.

There’s also a story and context to everything. Being tired doesn’t mean giving up! Au contraire: the party is just getting started. With a foundation in place, now the real fun begins.

When you believe in something with a level of conviction that is so deep, you’re not going to stop. You WILL find a path forward. Of course, there will be one or five thousand speedbumps along the way that do everything from exerting a soul-crushing blow to thwarting your confidence at every turn. But, when your “why” is inextricably linked to the core of who you are, you are determined to persevere no matter how tired you are.

That’s because your team is counting on you. You’re building something that’s bigger than you, bigger than your team, and even more grand than all the collective BS spewed by the naysayers telling you that it can’t be done. Or that you’re not the right person to get the job done. They tell you to just give up. Surrender. But you know that you have the leadership skills to keep your team moving forward, to inspire them when they’re feeling discouraged, and to make the tough decisions that will ultimately lead to success.

Do you want to talk about pressure? Resilience? You better have a backup supply of the latter if you’re going to foray into the world of lean startups.

The Realities of Running a Bootstrapped Startup

Incorporating as a company with all the legal and tax stuff, creating a community of coaches, building a team, going to market, securing pilot customers, developing a proprietary e-Learning platform AND a content library for soft skills — IN PARALLEL — was, in hindsight, overly ambitious. But we’ve done it.

The grind of operating a bootstrapped startup is beyond grueling and unlike anything I’ve ever experienced. And I’m a tough cookie. Battling breast cancer and an abusive spouse — at the same time — was so much easier on multiple levels. Here, I’ve bet the farm. That’s right, I’ve mortgaged my family’s home and depleted my savings to do this. For many, that’s too much risk, and that’s fair: we all have a different tolerance for it. For me, it is motivation to succeed. And, to be clear, I fully accept that this choice and this burden are mine and mine alone.

Learning from Mistakes and Moving Forward in Entrepreneurship

I’ll share this: one group of students that we were collaborating with had a negative reaction following our introductory Q&A sharing the history of, and vision for, STEERus. Note that I said that I mortgaged my home once, and not repeatedly to them. Three months later, I learned that sharing that detail made them “very uncomfortable,” “put them under an unreasonable amount of pressure,” and that I should have withheld that detail from them. I’ve taken their reaction to heart as I like to create safe spaces for people in my ecosystem, so I won’t make that statement again in conversation with others. That said, I sincerely hope that none of those students pursue a path of entrepreneurship; they appear to be lacking resilience and have little appetite for risk. As a founder, you need to get comfortable with being uncomfortable, like asking for help and asking for money.

I can err but I must learn quickly from the errors that I make. Regroup. Pivot. And move forward.

The pace is relentless — there are no days off and time for indulgent self-care. I read blogs about people taking an hour-long bubble bath each night, sleeping 8–10 hours, limiting their workday to eight hours, not working on weekends, and making time to doodle, daydream, and nap. Arguably, that level of self-care is worth aspiring to. But it currently eludes me, as my focus is on maintaining my productivity and pushing my startup forward.

On an average day, most founders have to wade through a couple of hundred emails. Keeping up with my network is nearly a full-time job and made it more challenging given all the e-communications channels. From Slack to Basecamp, WhatsApp, LRT, Lunchclub, Upstream, Instagram, Twitter, Facebook Messenger, Linkedin, and texting, there are days that I want to throw my phone into the Hudson River. But, without my network, which is correlated to my net worth, I have nothing. So I grind.

… story continues on Medium:


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