I’ve been having various conversations with current and potential clients over the past few weeks, and one theme which seems to be rising up is that of admirable persistence vs. persistent insanity, as in: when you’re working really hard in your business and the results just aren’t there, should you keep persisting? or not?

Admirable persistence, to my way of thinking, is, well, admirable. It’s the quality of sticking to your goals and plans and not letting obstacles or challenges stop you for long. Obstacles and challenges happen in any business, and don’t, by themselves, suggest whether you’re on the right path or not.

I believe that one purpose of entrepreneurship is to make us strong in our weak places. That means that wherever we are “weak” in our lives (such as in setting personal boundaries, saying No, dealing with anger or conflict) will show up as issues in our businesses too (where we take on too much work, overload ourselves with unnecessary commitments and avoid speaking the truth when required.) And that means that when we become stronger in these weak places in our businesses, we can, very often, carry these gains into our personal lives as well.

So, sometimes, an obstacle or challenge is a sign that you’re on the right path for your overall growth, and so you should keep going.

Then, on the other hand, there are times where there are so many obstacles and so many challenges that you start to wonder whether a) you’re really somehow stunted that you need all this growth, or b) if you’re on the wrong track.

Leaving aside the issue of whether you are really stunted (my guess is no), let’s talk about how you know when you’re on the wrong track.

I think there are 3 ways to know:

1) You are running into obstacle after obstacle, challenge after challenge- and each seems worse or somehow bigger than the one before. This, to me, is a sign that you might need to stop or back up and try another way. One of my personal hallmarks is that when I keep being challenged, it’s a sign to look closer. If the challenges are different from each other- and I feel like I’m stretching, but not breaking, I keep going, at least for a little while longer. But if the challenges start to come faster and faster, or I feel like I’m being stretched too thin, I stop what I’m doing. I try to walk the line between giving an endeavor a solid try, and working way past the time that it makes any sense. When I start to feel like it doesn’t matter how hard I try, nothing is changing- that’s a sign to me to stop.

2) You notice you are thinking about this problem or issue quite often; it’s taking up a lot of time in your psyche and energy. I see this often when clients and I starting to walk divergent paths. I find myself, almost randomly, thinking about a particular client more of the time and sifting through our most recent conversations without any real purpose or greater insight or understanding. Over time, I’ve come to realize that when I start thinking about a client a lot between meetings, with no additional action or insight, it’s a sign that our relationship needs to change, or end. In this case, the action would be to initiate a conversation or shift in the relationship- continuing to spend time thinking without doing is not going to move the relationship or situation forward. That’s a sign that some other action is needed.

3) You aren’t getting the results you could reasonably expect. Of course, it’s difficult to know for sure what is reasonable, but I do believe we each have a felt sense of what is reasonable to expect given our effort. When I work with clients to help them build their businesses, one question I ask is, “is your business growing in the way you expected?” If not, it opens up a good conversational space to look at why not. Sometimes, of course, my client’s expectations are too high- but, most of the other times, they have a sense that something isn’t quite working. You can ask this kind of question in your own business. If you were doing this kind of  business scan, where would the pain points be? What in your business isn’t growing as expected?

Once you identify this area, take a look at whether you are working smart in this area, or just working hard? If you feel you are being strategic and are experiencing obstacles that you can tackle, keep going. If, though, you feel that each effort is just running into the same old rut, it’s time to take different action. Get some advice. Seek support. Take a break. Do the opposite.

Any of these can help you make the shift from persistent insanity to admirable persistence.