When is it time to give up?

A recent topic submission posed the following questions:

“Have you ever lost your motivation to continue with your business? How did you know whether it was temporary or a sign of a bigger problem and do you have any suggestions for working through it?”

WOOF.

This is a big question, and there’s really no right answer here, but I’ll share some insights from my own experiences.

Have you ever lost the motivation to continue?

Personally, yes. Many times. Probably every 12-18 months for the past eight years.

Running and growing a company is an incredibly difficult challenge. That’s putting it mildly. It can really suck the life out of you if you let it. The stress. The long days and nights. The financial worries. It’s enough to drive anyone crazy.

On top of that, the last 16 months have been hell for a lot of business owners.

There was COVID and its immediate effects, but then also the aftermath that we didn’t see coming. (I suppose COVID is not a “was” - it’s a still is - no matter how much we want it to go away.) Somehow I am finding running my company even harder now than I did in Spring and Summer of 2020.

I’ve seen a number of people shut down their companies, and I usually applaud them. It takes a LOT of guts to acknowledge that the company specifically, or entrepreneurship in general, is not for you.

On the other hand, I think sometimes people give up too soon.

My company didn’t really start growing until year five. YEAR FIVE. Think about that. 

2013-2017 was five years of:

Massive financial turmoil. At one point, I drained my savings to make payroll, then had to transfer the balance on my credit card so I could have more time to pay it off. I felt like a failure, and some would say this is incredibly irresponsible (it kinda was). But I had a vision and I knew in my heart of hearts that we would get through it.

Dealing with big challenges and a lot of stress on a daily basis. Someone recently commented on a video of mine: “You’re only 35? Girl, you better listen to your stress.” When I got over being mildly offended (ha), I acknowledged the truth in that statement. I know exactly where every wrinkle and grey hair came from.

Making many other sacrifices to try to grow a company—I wrote about that here.

I thought about giving up many times, and I didn’t mainly because I am outrageously stubborn and I hate to fail. That said, I think if it went on for much longer, I probably would have thrown in the towel.

So, how do you know if it’s time to move on?

I don’t have a formula, but here’s a short story about how I knew it was time to move on from one of my other adventures, Women’s Entrepreneurship Week (WEW). Check the organization out here—now being run by Andi Sciacca and Kirsten Helgeson, two incredible leaders in Milwaukee!

WEW was never a money-making organization. I’m sure there could’ve been money in it, but figuring out how to turn WEW into a financially viable organization seemed like a big job that I was not ready to take on. It was basically the most time-consuming and hardest volunteer job I’ve ever had.

From 2018-2020, I ran WEW (alongside my two co-founders), my company Accelity, had 3 kids at home, and was working toward my pilot’s license (I’ll update you on that another day). I was straight up burnt out.

I knew something had to go.

So, I looked at each of my commitments and asked myself a few questions:

Am I enjoying this? You don’t have to love what you do every day (I think anyone that says they do is full of it). But you should like it more days than not. Grab a calendar and mark the days you love your company, and the days you don’t. Which is winning?

Does the time to payoff ratio make sense? Am I making money or equivalent connections, friendships, etc.? If not, will I in the future? If I’m not making money, can I afford to keep going?

Is it contributing to my long-term goals and big dreams? Where do you want to be in 10 years? 20 years? If your company isn’t in that picture, it might be time to find another path.

Finally, does this feel right to me? I am a firm believer that if you sit with yourself and your thoughts long enough, you will eventually know the answer.

Ultimately, after answering these questions, I knew I could not continue with WEW. My co-founders agreed.

As luck would have it, I emailed Andi and Kirsten asking how they might approach passing WEW on to new leadership, and they were interested. Not only did they have experience in this kind of work, they had a vision for how to expand and monetize the venture. It was truly serendipitous.

That was a long way to say: there’s no way to be 100% positive that you should keep going or throw in the towel.

If you’re in this boat, I hope this email helps you on your journey to figuring it out.