Some tasks are a joy to get rid of. Paying bills. Calling clients about finances.
Some task are more difficult. Like managing the delivery of services and believing it will be done the "right" way.
For me, the hardest thing I've ever tried to give up is sales. I used to fear that a salesman would sell something we can't deliver. But it turns out that this is pretty easy to control if you have an engineer involved in the sales process.
Hiring other people is partly about expanding your business. It's partly about expanding your potential. It's partly about taking some time off because you don't have to do it all.
And there's another big part: Giving up control.
When you hire someone to deliver services, manages finances, or do sales, you give up some control in your company. If you turn things over completely, you turn over control completely. That might feel good for awhile. But when things go sideways, they can go very bad very fast.
So you have to monitor, check up, and maintain a certain level of control. You don't want to meddle too much or micro-manage. But you need to be involved enough to keep things on track.
Unfortunately, one of the great challenges of hiring a sales person is that they need to generate enough money to pay for themselves AND take your business to the next level. And, if they stop selling, then you have increased expenses (from being at the "next level") without the revenue you'd come to rely on.
When you lose a sales person, your business contracts and you have to jump in and start selling. If you don't do this, the business will contract more. It can be very painful and drag you "off task" from the other things you've been doing since you didn't have to do sales.
The smaller your business, the harder this is.
Only one thing helps: Focus. Prioritize the one or two things you need to do right now to make payroll, get back on track, and get the machine moving again.
Seth Godin has a nice little book called The Dip. It's very important to figure out whether you're in a Dip or a crevice. Many people quit (or make bad decisions) when they're going through a dip. It can feel like a much bigger hole.
It's important that you don't quit just because you're in a dip.
At the same time, you need to also recognize when larger changes are needed and to stop doing things that don't work.
Sometimes we need to quit doing things. And that's very hard.