When to Persevere, When to Prune (on Moving On in Business)

Girls, you’ve got to know when it’s time to turn the page
— Tori Amos


The thing about becoming a successful business owner is that it requires (unless you’re super lucky, and probably even then) that you be willing to make changes. It’s a game of try something, see how it works, make adjustments, see how it works, make adjustments, see how it works.

I started with an etsy shop that sold quilts, among other things. Then I sold greeting cards wholesale to brick and mortar shops in three countries. Then I got into licensing. Logo design. I started a short-run print shop. Wedding invites. Elopement announcements. Business consulting. Brand design. Lettering and font design.

It seems that choosing the new things to try is always easy. (If anyone has an idea for how to make a successful business model in which all you ever do is just try new things, on and on and on forever, message me STAT.)

The hard part is deciding when it’s time to let a part of your business (or even the whole thing) go.

I saw an interview with Chris Guillebeau in which he suggested that it all comes down to two questions: Is it working? And Am I happy?

I love this, and I love to hate it. It’s so spot on, and yet it’s impossibly obvious and vague! 

Typically, when I come to the point where I’m questioning if it’s time to move on, I’ve already at least partially answered those questions. At some level, I know that things aren’t working and that I’m not happy. 

Reaching that point is how I know it’s time to make changes. It’s not necessarily how I know it’s time to move on.

So how do I know? Here are six questions I ask myself:

1. What do I wish were true about this offering/business?

Sometimes here I’ll hear myself answer something like, “Selling wholesale to boutiques would be great if only I didn’t have to actually sell to boutiques” and then I’m like Whoa. Yeah. I don’t actually want to be doing this. Nix this offering.

Other times I’ll hear myself say something like, “I would love designing wedding invitations if only I didn’t have to print, package, and ship them.” Boom. Sell printables or find a print shop that will handle fulfillment. Ok. Keep this offering; implement those changes.

2. Could I be completely passive about this offering for awhile instead of nixing it, and see how that goes?

I wrote a few months ago about how I’ve been having a lot of trouble with one of the companies I license designs to. Instead of cutting all ties, I decided to let that part of the business go dormant for awhile and see how everything shook out. 

I did the same with my etsy shop a while back. After years and years selling on etsy, I had the feeling it was time to close up that shop. Instead of doing that right away, I turned on vacation mode and gave myself time to see whether I missed it. I didn’t, and eventually I happily gave it up. 

3. What’s keeping me from moving on?

If I’m in angsty “should I stay or should I go” mode and I just don't know what to do, there’s usually something keeping me where I am (otherwise I’d have moved on already). Figuring out what that is can be crucial to deciding whether to adjust or abort. Am I hanging on because letting go will be embarrassing? Then let go anyway. Am I hanging on because I really love my clients? Maybe I could work with them in some alternate way.

4. Do I have anything waiting in the wings?

Now here’s where I get a little practical and a little less “follow your gut.” I’ll ask myself if I have any viable options waiting in the wings. New offerings, new business ideas, new job offers. Because if I don’t, if there’s nothing waiting there for me, I may decide it’s time to hang on despite all other signs pointing me to Drop-it-ville. Because I’ve got bills to pay, that’s why! But not only that. I’ve found that sometimes when I tell myself I have to slog through because I don’t have any other options, boy does my brain start working hard to come up with options.

5. If I knew back then what I know now, would I still start this business/product? Why? Or with what alterations?

I actually got the heart of this one from Ramit Sethi

This is the kind of question that helps when you’ve grown a business, but it’s nothing like what you thought it would be. Like when selling handmade pies becomes less about baking pies and more about marketing, selling, dealing with suppliers, etc.

Sometimes, asking this question can help you see that there are ways to make it more like you envisioned (maybe hire a manager to do those things while you bake pies). Sometimes, it helps you see that you don’t actually want to do what you’re doing.

6. What’s the absolute perfect solution to the problem of me not being happy with this business/offering?

The sky is the limit here. Really dig in to get to the point where you’re like, NOW THIS IS WHAT I’M TALKING ABOUT! Would the perfect solution be that your business magically disappeared? Would it be that tomorrow evening someone called you to offer you a job? Or would the perfect solution be that you only work four hours a day, four days a week and you take long vacations throughout the year? 

The thing with this question is that it doesn’t always answer your question, but it always helps you see what you could be working toward, and sometimes that’s enough motivation to get you to put your head down and get back to work.