5 things to consider before deciding to work for yourself

Listen to this article

When people ask me what I do, now that I’m out of television, I simply say, “I have my own business.”

The reaction is always the same.

“Wow, that’s so awesome, you’re so strong.”

“Good for you.”

“You’re so brave, I wish I could do that.”

Well, you can.

I did, and not because I am awesome, strong, or brave.

If you’re reading this you are probably bored, underappreciated, or stalled in your career. These are the adjectives many of my female colleagues use to describe where they are professionally.

My career unrest did not come while working from home during the pandemic like it has for millions of people who are now seeking a change, engagement, or work-life balance.

My “great resignation” was forced upon me during the recession when employees were suddenly told to do more with less. The new economy left everyone holding an iPhone. Technology was smaller, communication was faster, and employees were trying to keep up while keeping their head down.

It was a typical Thursday afternoon, and I was summoned to come upstairs. I could leave, or accept a significant pay cut and a new night schedule that would make it difficult as a single parent to care for my young daughter.

I left with my severance package and a bruised ego.

I was lost. I had not been in the job market in 30 years.

Months of applying for positions online left me rejected by the corporate world. Fed up, I decided to pivot; I stopped scrolling Indeed and realized that I could make money working from my dining room table.

If no one would give me a job, then I was going to create my own.

Seven years ago, I became a solopreneur.

I share my story after talking with so many women in my demographic checkbox who struggle with the same question: try to survive the next 10 or 15 years or thrive?

Here are five things you may want to consider before becoming your own boss.

Comfortable With Being Uncomfortable

Working for yourself is not for the faint of heart. You must be highly motivated and disciplined with your time. There are bills, slow months, and days when it feels like the responsibility will swallow you up. Money will come, eventually. The voice in your head will keep saying, you can’t do this. The payoff is freedom over structure. I can be a present parent, I have the privilege of caring for my aging mother, and I learned that having balance is more important than a salary that strangles you.

Passion for Your Work

Working for yourself requires a lot of passion, energy, and excitement about what you are doing. You are ultimately selling yourself, and your service and clients must buy in. As the founder and employee, you are the brand and responsible for all of it, so you better be hyped about what you are creating. Being small requires a big effort.

Out of the Box Thinking

Working remotely was not so common when I started my business.  I created a niche concept to offer potential clients. Most days, l I needed my phone and the internet.  Beyond sending an email, I was awful with the computer. I spent eight weeks — every Wednesday night at the Brighton library — taking a Word and Excel class for beginners. It was humiliating.  Recognizing you need help is a strength.  There are webinars, tutorials and free classes that can educate you on just about anything. You must always be willing to learn something new.

You Must Love Coffee

I am grateful for all the people who met me for coffee. Connection is key to starting your own business. Find people you trust and ask them for names, information, and advice. Attend networking groups, pitch ideas, and seek out the pay-it-forward people who have been in your shoes. I have picked the brains of more people than I care to admit.  You may not always get the sale but remember, you only need a few good paying clients to start your business. People want to help, so don’t forget to ask for what you need.

If Tom Brady Can Do It

Do not let anyone tell you that you are getting too old to still be in the game. Societal norms push employees into retirement too soon. Tom Brady is changing his workplace by proving that you can still contribute at a high level beyond your “retirement” age. You can even change your mind after you retire. I was let go a few months shy of my fiftieth birthday when I started my business as a solopreneur. I am thankful everyday that I did not get any of the jobs I applied for.

Taking control of your career or trying something new will not suddenly make you happier, but it gives you the chance to be.

Robin De Wind is a former Rochester broadcast journalist who now runs Robin De Wind Media Group, a video content marketing business. Learn more at rdwmediagroup.com.