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Rude Awakenings: The Lessons I Learned When I Quit Corporate to Be My Own Boss

4min read
Career

Ok, I'm Outta Here.

If you haven't heard already, being an entrepreneur is HARD. It's extremely risky; there's a lot of late nights, salary loss risk, a lot of uncertainty, and the list goes on and on. These are the "known unknowns," so to speak, and they are challenging, but expected.

The real challenge, the single largest factor to prepare for is the steady flow of, in the words of Donald Rumsfeld, "unknown unknowns," you must overcome on a daily basis. This cannot be overstated. As a leader in a startup, you will be confronted with a broad and largely unpredictable set of conundrums, and the only way to prepare is to anticipate their arrival with an open mind and a deep breath.

The transition period is unsettling because while you're trying to grow your idea into a tangible entity, you're thrown obstacle after obstacle that tests your perseverance not only mentally but physically as well.

I had a solid career in Brand Marketing at the largest food company in the world— a position that I had dreamt of earlier on in my career. I wanted it so badly that I got an MBA just to qualify for it. This coveted position would open the doors to significant career advancement opportunities. But something was amiss… at the end of the day, the organization of which I was part, while spinning a tale of innovation and respect for, "out of the box" thinking was entrenched in conservative and traditional ideas with deeply shortsighted planning. I said, "Ok, I'm outta here."

Failing Fast

Soon after leaving my job, I learned the hard truth that anything that can go wrong, will go wrong. Rose-colored glasses blind you from the lurking dangers you need to path around. Being a realist is vitally important, and the faster you accept the situation that arises, the faster you can act to correct it. When you embrace this is a natural part of the entrepreneurial process, the resulting incremental success will help ensure long term survival.

I also learned the hard way that sometimes you have to come to terms with killing your "best" ideas. An early company of mine, a beverage line, was destined for failure. We had no major customers lined up, our formulation had too short of a shelf life requiring a tiny sales window, and it required a large amount of capital for the initial production. Don't get me wrong, the actual product would be GREAT, and I've recently seen a similar iteration of the product in the beverage aisle, but that's not always the point - at the time we were not capitalized to make that product and coming to terms with that notion is KEY. Venture capitalists call it "failing fast," and if it ain't gonna work, it's better to decide to can it, sooner rather than later.

Partnerships

A major career change will affect all arenas of your life, least of which are the relationships in it. It's been said that you should never work with friends or family, and I've learned the hard way that this adage has stood the test of time for a reason. This isn't to say it's impossible, but there will, like any other relationship, be challenges as your circumstances and dynamics undergo changes. This may be with your business partner, your family, or even your friends as your priorities shift to focus on your newfound project. If you're one of the lucky ones, your relationships may remain unaffected by the major adventure that you've chosen to undertake. If not, the good news is that you can prepare for the inevitable ups and downs.

Business partnerships are like any other relationship—you need to be transparent and explicit not only about what your expectations are for the business but also your relationship in the event that your venture doesn't work out. We all hope relationships won't sour, but it's good practice to anticipate and prepare for the possibility that it might. Take stock of your support system: Who will you turn to outside of your partnership to discuss problems? From whom can you get honest but constructive feedback? Whether a support system means finding a seasoned mentor in the industry, checking in more frequently with a therapist, or taking the time to destress with girlfriends at a weekly brunch, schedule me-time just like you would any other meeting or event.

Your Company is Not You

As an entrepreneur, you have to be flexible to pivot when necessary. So when my goal of starting a beverage line didn't pan out, I reached into my back pocket to see what other ideas I had in the past that could come to fruition. I took all those ideas and worked on them simultaneously to see which project could get the most traction. From this journey materialized DoggieLawn, an eco-friendly alternative to pee-pads that just seemed to naturally make sense for a busy pet owner like myself.

It's important to prepare for failure as much as you would prepare for success. Failure is a natural part of this process. And it's so easy to dwell on it when it feels like everything is falling apart before your eyes.

But if and when things go awry, be solution-oriented instead of ruminating over what could have been. Remind yourself that running into obstacles is normal, and success doesn't happen overnight, despite what our social media inundated culture would have us believe.

You can easily become overwhelmed, depressed, or even take it personally. This is why I advise women who are thinking of making the big shift from corporate to being their own boss to prepare for failure as much as you would for success. Your ideas and your company are not YOU. When you ditch a product line or shutter a company, you must not shutter yourself. Meditate on this notion before you even start - you'll thank yourself later.

​4 Min Read
Business

Please Don't Put Yourself On Mute

During a recent meeting on Microsoft Teams, I couldn't seem to get a single word out.


When I tried to chime in, I kept getting interrupted. At one point two individuals talked right over me and over each other. When I thought it was finally my turn, someone else parachuted in from out of nowhere. When I raised and waved my hand as if I was in grade school to be called on (yes, I had my camera on) we swiftly moved on to the next topic. And then, completely frustrated, I stayed on mute for the remainder of the meeting. I even momentarily shut off my camera to devour the rest of my heavily bruised, brown banana. (No one needed to see that.)

This wasn't the first time I had struggled to find my voice. Since elementary school, I always preferring the back seat unless the teacher assigned me a seat in the front. In high school, I did piles of extra credit or mini-reports to offset my 0% in class participation. In college, I went into each lecture nauseous and with wasted prayers — wishing and hoping that I wouldn't be cold-called on by the professor.

By the time I got to Corporate America, it was clear that if I wanted to lead, I needed to pull my chair up (and sometimes bring my own), sit right at the table front and center, and ask for others to make space for me. From then on, I found my voice and never stop using it.

But now, all of a sudden, in this forced social experiment of mass remote working, I was having trouble being heard… again. None of the coaching I had given myself and other women on finding your voice seemed to work when my voice was being projected across a conference call and not a conference room.

I couldn't read any body language. I couldn't see if others were about to jump in and I should wait or if it was my time to speak. They couldn't see if I had something to say. For our Microsoft teams setting, you can only see a few faces on your screen, the rest are icons at the bottom of the window with a static picture or even just their name. And, even then, I couldn't see some people simply because they wouldn't turn their cameras on.

If I did get a chance to speak and cracked a funny joke, well, I didn't hear any laughing. Most people were on mute. Or maybe the joke wasn't that funny?

At one point, I could hear some heavy breathing and the unwrapping of (what I could only assume was) a candy bar. I imagined it was a Nestle Crunch Bar as my tummy rumbled in response to the crinkling of unwrapped candy. (There is a right and a wrong time to mute, people.)

At another point, I did see one face nodding at me blankly.

They say that remote working will be good for women. They say it will level the playing field. They say it will be more inclusive. But it won't be for me and others if I don't speak up now.

  • Start with turning your camera on and encouraging others to do the same. I was recently in a two-person meeting. My camera was on, but the other person wouldn't turn theirs on. In that case, ten minutes in, I turned my camera off. You can't stare at my fuzzy eyebrows and my pile of laundry in the background if I can't do the same to you. When you have a willing participant, you'd be surprised by how helpful it can be to make actual eye contact with someone, even on a computer (and despite the fuzzy eyebrows).
  • Use the chatbox. Enter in your questions. Enter in your comments. Dialogue back and forth. Type in a joke. I did that recently and someone entered back a laughing face — reaffirming that I was, indeed, funny.
  • Designate a facilitator for the meeting: someone leading, coaching, and guiding. On my most recent call, a leader went around ensuring everyone was able to contribute fairly. She also ensured she asked for feedback on a specific topic and helped move the discussion around so no one person took up all the airtime.
  • Unmute yourself. Please don't just sit there on mute for the entire meeting. Jump in and speak up. You will be interrupted. You will interrupt others. But don't get frustrated or discouraged — this is what work is now — just keep showing up and contributing.
  • Smile, and smile big. Nod your head in agreement. Laugh. Give a thumbs up; give two! Wave. Make a heart with your hands. Signal to others on the call who are contributing that you support and value them. They will do the same in return when your turn comes to contribute.

It's too easy to keep your camera turned off. It's too easy to stay on mute. It's too easy to disappear. But now is not the time to disappear. Now is the time to stay engaged and networked within our organizations and communities.

So please don't put yourself on mute.

Well, actually, please do put yourself on mute so I don't have to hear your heavy breathing, candy bar crunching, or tinkling bathroom break.

But after that, please take yourself off mute so you can reclaim your seat (and your voice) at the table.