Caution and Grit: How to persevere through the hard times of self-employment

Maggie Karshner
4 min readJul 20, 2022


I know there are plenty of you out there reading this who are not yet ready to take the leap into self-employment. Or maybe you have, and you’re not yet confident that your business will stay afloat. I get it. Self-employment can feel scary. It’s a strange new world lacking many of the landmarks you’ve grown accustomed to.

And, just like when you move to a new city or neighborhood, it can help to get a little tour of the neighborhood beforehand. As an eight-year resident of the self-employment neighborhood, let me tell you about the biggest eyesore in this neighborhood: the hard days.

You will have hard days.

You’ve had them before, and they’ll still happen, but they’ll be a different flavor.

You will get to the other side of them.

You’ve made it through all the past hard days. Why would now be any different? Even if your business has to take a back seat for a minute or needs to close and be reborn anew, you’ll get through the bad days.

You might be changed by them.

Unlike some other hard days, self-employment means you’ve chosen these hard days. Maybe not specifically each and every day. But there’s definitely more choice in it than when an employer makes a decision that makes their employees’ lives more difficult. When you chose the challenges it makes learning from them more fun.

My hardest day in business was Feb 27, 2017.

This was less than 4 months after the 2016 elections. The shock and despair had not yet abated. And now the news cycle was full of absurd and terrifying headlines at an unprecedented cadence. I (and plenty of others) were in a bit of a stupor.

My business was on the cusp of celebrating its 3rd birthday. I held close to mind my mom’s benchmark that it takes at least 3 years in business before marketing really has a life of its own. Things had been growing over those first few years and I was almost there.

On the 27th, as I do every month, I check in with my finances and decide how much I pay myself for the month. (More on how I do this in my online course: How Does Paying Myself Work?) I looked at my bank balance and thought “hrm, that seems low,” but dutifully put it into my calculator. Then the situation was clear. I had only enough to cover my office rent and a couple of other business expenses. I didn’t have enough to cover all my business expenses, much less pay myself. In the launch of a business, this isn’t unheard of. But this hadn’t happened since my first year in business, and now I was nearing my third. I was stunned.

My panic didn’t come from not being able to feed or house myself. I still had some of my start-up savings to draw from. My basic needs were covered, but my belief in my business was shook to the core.

Maybe this wasn’t as viable a business idea as I thought? Was political instability shaking individuals’ faith in themselves? Was that faith necessary for the success of my business? Maybe I wasn’t about to hit marketing nirvana and I’d actually just tapped out my whole market?

I held these big questions and persevered. About two months later, the truth emerged. In my post-election stupor, I had coasted in my business. My marketing energy had dried up. If you stop putting in, then you stop getting out. As soon as I got back on my marketing, the clients emerged and I was back on the right path.

Was it hard? Oh yes. Did I make it to the other side? Also yes. Was I changed by it? Definitely.

The lesson I learned was that coasting is fine, but it can’t last more than a month or so. Marketing needs to be a constant element of my business, no matter what chaos is going on in the national news.

I carry this lesson with me with every cataclysmic news headline. Through the pandemic, insurrection, supreme court rulings, reports of inflation and whatever next thing surfaces in the news. Yes, these have repercussions that I do respond to. But my business isn’t at risk. And even if it were, coming at it with a level head, continuing to invest energy into my business, and making measured adjustments is going to serve me better than anything else.

That’s my experience with the eyesore in the neighborhood of self-employment. What’s yours? Even if you don’t think self-employment is the right fit for you, the lesson you can learn from this story is: tackle the hard days as an opportunity to learn and you’ll be great at whatever you’re trying to accomplish.

Originally published at on July 20, 2022.



Maggie Karshner

Maggie is a business coach who helps launch and grow self-employed businesses. Learn how she could help you at