At First You Do Not Succeed, Try, Try & Try Again?



There comes a time in everyone’s life when you are faced with the decision whether to persevere and continue striving or let go. Do you try harder, push faster or do you surrender completely?

I consider this to be a crossroads where discerning wisdom is crucial. I have been there many times in my life: in my marriages, with different business ventures and while training for certain athletic goals.

As I child I was taught, “At first you do not succeed, try, try and try again,” and “Never give up!” and “Don’t be a quitter,” but I have also learned later in life that sometimes you just need to “surrender to win” and that surrendering does not necessarily mean giving up.

So which one is it? For me, the key is willingness. When I just do not have the willingness to try any longer, then it’s time to let go, even if releasing my grip is painful.

I have had the joy and deep sorrow of coming to this crossroads, recently in my marriage, as well as with a business venture that I birthed two years ago, so my experience with this question is fresh.

With my marriage, I was clear that I had a willingness to continue to work on the marriage. I felt as though I had not done everything possible within my power to save the marriage. I felt as though I still had room to grow and things I wanted to change within myself that would in my opinion make me a better partner.

In applying the serenity prayer, “God grant me the serenity to accept the things I cannot change, the courage to change the things I can and the wisdom to know the difference,” I had the foresight to see that there were things within myself that I could change for the better that would make me a more compatible partner.

I knew that if I did not make these changes, they may come up again in future relationships. I still loved my husband dearly, therefore, I had the willingness to persevere, take action and do some challenging inner work. Work that required honesty and humility and ultimately allowed me to show up more wholeheartedly in my marriage.

I stumbled into this same crossroads recently with a business venture I started with my friend two years ago out of my garage. It was a labor of love for the first year. I loved the products and the mission and it served as an excellent creative outlet for me while I was working at a boring and monotonous day job.

I learned a tremendous amount about social media marketing and bringing products to market. I also had the great experience of doing a Kickstarter video. But, after two years, of making soap in my garage, selling products on weekends, managing people, managing operations, scrambling to find capital to keep operations going and basically running a small business on the side while raising three children and working full time, I hit a wall. Imagine that.

Starting a new business takes serious grit and tenacity. I started it. I put my heart, my soul and my pocketbook into the business. Two years later, I no longer had the willingness to continue to put that kind of energy and sweat equity into the business. Truth be told, I started my own legal practice last November and my passion has shifted to focusing on empowering entrepreneurs to help them launch their businesses and any time I had above that, I want to be spending with my family. My priorities had shifted and I had to honestly accept that I just no longer had the willingness.

“I don’t ever give up!” Elon Musk, self-made billionaire has said. No offense, but that seems pretty one dimensional to me. I just do not agree with that anymore. The only constant is change itself and to deny myself the experience of change for fear of judgments, no longer seems like a viable option.

If the dream I am pursuing shifts and I no longer have the passion for what I started, it’s ok to surrender to win. For me, it all comes down to willingness. At an instinctual level, I know that when I no longer have the willingness, when I have hit that wall, there is no sense in denying what is true for me — it’s simply time to let go. It’s in the letting go gracefully that allows everyone in the situation to move forward with dignity.

Jennifer Clifton, business attorney, Viewpoint Law Group,, 458-206-9440,

(Photo above | Cascade Business News)


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