Most entrepreneurs (and those who want to be) struggle with the question of when to quit and when to keep going. “Should I stay or should I go” maybe a fairly constant refrain. I’ve certainly been there myself over the years and it can be a major distraction, if not handled properly.  While at the same time, if you quit right, it can be exactly what you need to take the next steps, go even deeper, get even more committed and see rapid expansion and growth.  Here’s how to do it well.

Before I get into the strategy, I’ll share two contrasting experiences I’ve had with quitting as the path to rapid expansion and growth. The first will show you how to quit the healthy way and the second will show you how quitting can go awry.

First, a client. I’m working with two women in a new partnership. I’ll call them Betty and Jane for ease of communication. This is not their names.

Betty started a version of the business originally and brought Jane (her best friend) in as a $10/hour employee to help with administrative matters.  Over time, Jane took on more and more responsibility and Betty began to get the sense that maybe she could bring Jane in as a partner in the business.

That’s when they contacted me.  On occasion and when it’s just the right situation, I work with private clients to support the creation of a partnership relationship or to help partners move through difficult experiences to deepen in their working relationship.

When I first met with Betty, she wasn’t necessarily thinking of giving half of the business to Jane. She was thinking that maybe she would still own the business, and call Jane a partner, but really Jane would be a high level employee.  After talking with Betty for a while, it became clear that she really wanted Jane on board as a full partner and that’s what Jane wanted too.

So we began to structure their partnership.

{Side note: in the past, I have made the grave mistake of calling people partners, but not really structuring the business relationship as a formal partnership and it was the death knell of the relationship and put the business at massive risk. If you are doing this too, stop now and get into alignment with what’s actually true, not just in words, but in action and formal documentation of the relationship.}

As we began structuring their partnership, all sorts of resistance began coming up for Betty.  She began to confront the reality that she felt totally responsible for bringing in all the money (she’s the front facing part of the business that makes the sales) and she began to feel burdened by the weight of the partnership, rather than relieved by it.

She contacted me for clarity.  Maybe this partnership wasn’t the right way to go. Maybe it was and she was just being too needy. Maybe she should just stuff her feelings under the rug and deal with them herself.

{Side note: how often have you stuffed your own feelings under the rug because they seemed like they might be too much for your partner to deal with?  It’s never the answer, trust me on that one. If your partner can’t deal with your feelings, you are not in the right partnership. And, it’s up to you to learn to share your feelings in a healthy manner, not stuff them under the rug or anywhere else.}

After talking out her feelings with her life partner and writing them out to me in an email and then having a phone conversation with me, Betty was finally ready to go to Jane and share what was coming up for her.

They had a couple of conversations on their own and then we had a session altogether. During that session, Betty quit the partnership.

Jane and I created the space for Betty to explore what it would look like if she really did quit and go back to the one-woman show she had been operating up until that point.

Betty felt that possibility all the way through. Fully entertained it. In her mind, she said “I quit!” and liberated herself from the burden of the partnership. As she did that, she was able to envision what her life and business would look like without the partnership and go beyond the fantasy of returning to a one-woman operation and what that would really mean for her life — back to doing everything herself.

Through that process, she was able to re-engage in the partnership fully and make a conscious choice that while there were some things about the partnership that were burdensome, the fantasy of becoming a one-woman show again wasn’t really what she wanted. It was a fantasy that was taking her out of being fully present in the relationship.

Once she was able to move through that fantasy — by going there and actually saying “I quit” and playing that fully out — she could come back to the partnership relationship with clarity about what she would need to stay in the relationship and have her needs met and meet the needs of her partner.

And once that happened, Jane could fully step in to meet Betty and relieve some of the burden Betty felt and show Betty what real partnership looks like.

{Side note: for Betty and Jane this meant that Jane is stepping in and sharing the financial responsibility that in the past was all Betty’s, by using her own credit resources to invest in the next stage growth of the business.}

I’ve quit many times in the past. Usually it comes in the form of me deciding to quit serving lawyers. I’ve got a love/hate relationship with my business that serves lawyers and teaches them how to step into a new law business model I created whenI was in private practice (that has them love their law practice and be loved by their clients) because I carry a belief that my lawyer clients can’t and don’t accept all parts of me (which isn’t actually true), so periodically when my “Ali part” feels unseen and unappreciated, I have to quit to remember.

In the past, when I didn’t know how to quit in a healthy way, I actually did quit. I fired everyone, closed down the business, and filed bankruptcy — just to prove to myself that I could quit and have the freedom I was longing for — only to remember that I love serving lawyers and I am uniquely designed to help them love their lives and practices and be loved by their clients. Oops.  All that was not necessary. But I didn’t know at the time that I could quit in a far healthier way.

And frankly, I didn’t have the right people in place to hold space for me to quit.  So the people I was talking to about quitting urged me to actually do it. Walk away, file bankruptcy, give it all up. It’ll be fine, they said. You’ll come out the other side a better woman.  And while all that was true, and I am a better woman on the other side of it, it could have been handled with so much more ease and grace.

So today, when I feel the urge to quit, I invite someone I trust (generally a coach I am paying who has specific skills in this area and can create the safe space for my exploration without getting caught up emotionally in the words I am saying) to hold space for me to feel it all the way through.  When I am able to do that, I can quit in a healthy way without throwing everything (and everyone around me) into upheaval.

Next time you want to quit, I urge you to do it.  Safely. In a container. Held. Supported. And then, after fully exploring it, if you still do actually want to quit, you’ll do it intentionally and with a well thought out plan that impacts yourself and those around you in only the best and highest ways because the truth is that how you quit one thing impacts how you start the next every time.  Quit with love.