Gary, a late-50s business owner, feels trapped by the company he built and fears both burnout and returning to salaried work. The host offers three steps: take a vacation to test if the business needs you, delegate tasks only you do, or shift to low-margin flexible work instead of going back to a traditional job.
Anyone else feel stuck in their own business? Hello, I'm new here. My name's Gary. I'm in my late 50s, and to put it bluntly, I feel stuck inside my own business. At the risk of sounding defeatist, I feel like I'm running a fun-free loop, grinding slowly towards failure. Industry changed faster than I could adapt. Bigger agencies coming in, blah, blah, blah. Somewhere along the way, this stopped feeling like something I chose and now feels like something I'm chained to. The only future I see at the moment is bleak. A worn-out version of me grinding away into my 60s and beyond, unable to retire properly and too I'm tired to keep going. 10 years of sunk effort makes walking away feel like a failure, but struggling on feels just as hopeless, to be honest. Is this a midlife crisis? I'm not sure, but I worry about trying to find salaried work at my age. Whew, Gary, you're not alone. So many business owners feel this way. They feel stuck, and this is why you're what I would describe as an accidental entrepreneur. You probably didn't even intend to get in this business. You just woke up one day and it was here, and now you're kind of burnt out because you built a prison around you, not a business. My first question to them is always, when was the last time you took a vacation? When you're burnt out, when you're feeling like Gary, step number 1 is go and take a vacation. What's the worst thing that could happen while you're gone? The whole thing implode? You're basically ready to blow it up anyways. What would need to be true about my day-to-day work for me to actually enjoy doing this business? What we find all— more times than not as business owners, we wind up taking on the stuff that nobody else wants to do or the stuff that nobody else can do. It always winds up trickling down to us. What doesn't get done? I don't know. Let's figure that out along the way. But if you haven't taken a vacation, if you haven't looked really closely at your job and maybe rewritten that, been intentional about that, I would try that first. If at the end of the day you're still not loving your business, third advice: flee to margin. But don't just blow the whole thing up and go back and get a job. You're assuming that you're gonna like a job more than what you have right now. You're gonna feel just as trapped there. So let's see if we can make this thing work. You can always go and get a job at any point in time, which is why it should be your last possible option.
