Lessons From Year One As An Entrepreneur

Photo by Brooke Lark on Unsplash

To be honest, and provide a little context, even after spending over a decade dreaming of working for myself, I never thought of what I’d be doing as entrepreneurship. It always seemed like whatever I did wouldn’t be quite so easily summed up. Like, a white man probably didn’t write a book about it. Over a year in, I still don’t dream about or see myself as a Business Owner. I hire people to do things for me, but I don’t have visions of employees and a leadership team. The primary goal is not to have to work for anyone else unless I choose to.

I’m also starting my coaching and consulting business as a middle-aged single mom — like sole custody, caretaker, and provider-level single mom. I once introduced myself this way to a zoom room full of women business owners and one said in the chat, “Sole custody is NO JOKE!” I think about that moment of validation from a stranger at least once a day. And, of course, I’m still trying to keep my too young to be vaccinated children from catching COVID in an increasingly messed up public health crisis response. So, I’m busy and stressed.

Which is to say, these lessons might not be the ones you’re expecting, but if you relate at all, they just may be the ones you need. Let’s get to it.

Even when you’re doing it alone, don’t do it alone

Sub-lesson: The other people you do it with will probably be people you were not close to, or even knew, before.

I’ve shared a bit before about how I fell in love with networking, and how lucky I was to have people brought directly to me who have helped me along the way. This was critical to my progress, not only because having people to share with and learn from when you’re starting something new is so helpful, but also because most of the people already in my life could not relate. I refer to it as being on the inside or the outside — the inside being employed at a corporation, which includes nonprofits (but that’s a rant for another day). The challenges and successes on the outside are really different, and I needed people who could at least understand me, and at best help me with their advice, commiseration, or services.

Being able to accept that I needed help, find the help I needed, and then actually accept the help was a part of the process. I had to unlearn a lot of stubborn independence, and that involved checking in with my own mental health and brain wiring. This was scary and amazing work. Sometimes I had to stop doing other things, even things related to my business, to get through it. But I never stopped connecting with the people who showed up for me in other parts of the process. When people talk about manifesting, this is one of practical things they’re actually doing — creating a new reality through new relationships. It’s not actually magic.

Get ready to also have a whole new relationship with time

TL:DR on this lesson — Working 5 days a week 10 hours a day is not an actual measure of productivity, but a little structure still helps.

Everything went into lockdown 3 weeks after the 24 hour period in which I was laid off and started my own business. I had no childcare, no partner, and no real backup for my kids who were in first and fourth grade at the time. I’d been in pretty severe burnout for at least a year already after a traumatic divorce and toxic workplace situation and a move with my kids to a new state. I was A MESS.

But, all of a sudden, I no longer had to rush to remember lunches and school supplies and shuffling children out the door. I didn’t have a commute or a single meeting that I didn’t make myself for my own selfish reasons. I was trapped by remote schooling and not being able to leave my house, but I was also weirdly free. It felt sort of dangerous and irresponsible. If I wasn’t spending 60 hours a week in mostly useless meetings, did I even exist? Sure, during every remote school day from March 2020 through May 2021, I was interacting with a child every 15 to 30 minutes, but I had complete control over the intervals in between as long as I didn’t need to leave my house.

When I realized that the first quarantine summer would bring even more freedom, I took things too far. “My time is my own!” I’d exclaim to people asking me how things were going. I worked when I wanted to work, late at night, on the weekends, no one else owned my time anymore, there were no rules. It was a temporal rumpspringa. My not yet late-identified ADHD had a field day. I felt alive!

Then I started getting business, and my clients had apparently not received the memo about time’s inconsequentiality. I had standing meetings booked on Sunday mornings and Friday afternoons, and every other day of the week. I became extremely protective of Saturdays. While my client work took up business hours, my business work took up after hours. I was making more than my take home pay from my last VP position each month, and I was making myself sick.

I learned a hard lesson that time wasn’t my own in a skipping through daisies way, but in an oh shit I’m only accountable to me way. I am still figuring out what this looks like for me, and am extremely cautious about overinvesting my time, only adding new work when it feels sustainable. This is a scary way to do things, but I’m determined to get to the skipping through the daisies version of time being my own.

You will surprise yourself

As if changing your relationships with other humans and time isn’t enough, a solid year plus into entrepreneurship will likely change your perspective on you. I’ve found there are two reasons people strike out on their own: they have a great idea, talent or passion, and/or they don’t want to work for anyone else anymore. Either way, there’s a different kind of motivation, a different something to prove, when you commit to working for yourself.

Following that motivation will lead to more humbling moments and true wins than you can imagine at the start of the journey. How I’ve responded to obstacles and opportunities has sometimes defied logic and good strategy. I’ve worked against or resisted my own advice for others lots of times. I’ve been calmer in moments of slow business or hard choices than I ever would have dreamed possible. I’ve valued myself and my time and my safety in ways no one else could or would be able to.

There was a tipping point somewhere in feedback from the people I was working and engaging with. I realized I was actually helping people and I felt successful. Even though I would rather give my right big toe than go back into a traditional corporate environment, if I had to, I’d still feel like a champion at doing this. Time well spent. I’d never had an idea of what success would be until I felt that feeling. It’s nothing like I was told to aim for, and that understanding changed everything.

Your only lifelong commitment is to yourself

I have totally rehauled my website 5 times in the last year and a half. I’ve changed my logo 3 times. My business premise continues to be a moving target. I’ve got at least 3 possible well thought out products I could launch. I might get snapped up by a business that meets my needs as much as I meet theirs tomorrow. I could have two weeks of kids in school and then another year with them at home.

Circumstances change, businesses evolve, feedback shapes new moves, opportunities show up out of nowhere sometimes. My second and third iterations of my website were heavy on my why, my process and my values, and while my web copy may be different, those three things are not.

The only times I get stuck are when I’m stuck on staying the course with an idea or process that isn’t working. Then I have to ask myself why I refuse to change, and if the answer isn’t related to my own best interest, I get unstuck by refocusing on me.

That involves remembering that people who don’t get what I’m doing don’t matter, and people who do will stick around for the ride, so I don’t need to worry about either. It also means believing I’ve got a lot of life ahead of me to figure things out. That’s what I’m committing to, not a product or service or brand, but continuing to do things in a way that honors my why, my process, and my values for as long as I have the privilege to make that choice.

I’m sharing this because a big part of my purpose is to prove there are better ways to use our skills and knowledge that don’t involve manufactured competition, unqualified oversight, and a focus on money and power over people. To tell you the truth that it’s still hard, but in a different way, and in my opinion exponentially more rewarding. And to reassure you that if you’ve been wondering, there’s space for you out here.

This article was originally published on LizaDube.com



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