How — and when — to question your goals.

Sandra Lewis
Mar 31, 2017 · 5 min read

As a startup CEO, my tendency is to push through obstacles to achieve goals no matter what. And, to be sure, I can attribute a great deal of our success to building a culture that values not giving up.

That said, sometimes goals get in the way, and the best course of action may be to change or abandon them.

But how do you know if that’s a wise decision — or simply taking the easy way out?


The first time I let go of a huge life goal was a few years ago, in my personal life. My husband and I are fortunate to have jobs we can do from almost anywhere, and five years ago we decided we’d had enough of New York winters. Wouldn’t it be awesome to move to Portugal, where it’s warm year-round, the hikes are gorgeous, and our two dogs could chase the odd rabbit? Full of optimism, we packed our belongings (and the dogs), and set out for Europe.

Weird things happened as soon as we arrived. Upon crossing the threshold of our temporary rental house, I twisted my ankle. A few days later, I became violently ill. Our dogs, normally happy and fun-loving explorers, wouldn’t venture outside.

Still we plowed on. “We’ve come all this way and we’re going to make it work!” we told each other. We convinced ourselves things would get better.

After a few months, we found a beautiful, reasonably priced house with loads of land, so we put down a deposit. But a few days before signing the contract, we went for a final viewing and walked the land. Within minutes, our eldest dog, Neela, started shaking violently and crying out in agony. We found out later that local shepherds had laid down poison to protect their flocks from wolves. An hour later, despite a local veterinarian’s best efforts, Neela was dead.

Our second dog barely made it through, but the shock finally woke us up to the reality that, as great as Portugal was, it wasn’t working out for us. We had done everything in our power to make it work, but as we crossed the border back into France, it was like breathing fresh air for the first time in months.

Me with our best boy, Neela (~ 2010)

How to Make the (Gut-Wrenching) Decision to Give Up On a Goal

In business, too, goals can become toxic. The challenge, of course, is identifying when to abandon (or change) a goal, and when to press on.

As a serial presser-on, here are a few ways I’ve learned to do that:

#1. When goals conflict, figure out which one is more important

As an entrepreneur, you’ll inevitably encounter situations in which your goals conflict, and you’ll be forced to choose between them. For example, last month one of our team members asked to be reassigned from a large client she had supported for five months. That put two of my goals in conflict: I want to offer consistent, reliable service to our customers; on the other hand, I want joy to permeate everything we do.

After reviewing the situation, I realized that our team member had given it her all and that, despite her efforts, the collaboration wasn’t as uplifting and rewarding as it could be. Making a change to a client-assistant partnership was a hard decision, but everyone involved — the client, the new assistant, and the team member we transferred — have benefited.

#2. Put on the brakes before making the call

Almost nothing is so urgent that it doesn’t allow for an overnight think-through. More than once, someone on my team has slowed me down and reminded me that it might be better to leave that pushy email in draft and revisit the situation in the morning. Boy has that paid off!

When it comes to making decisions about objectives, too, it’s worth taking the time to understand what’s at stake and why you’re either trying harder or moving the goalposts. In my experience, not making that decision in the heat of the moment and without thinking it through — has always been beneficial.

#3. Stay mindful about why you set a goal in the first place

Over the years I’ve learned that it’s easier to decide whether to stay on track or adjust course when I go back to why I set a goal in the first place. For instance, I have goals around media exposure for Worldwide101, but in the past I would settle for any kind of exposure — even if it would never be read by people we want to reach. More recently, I lowered my targets for quantity and raised the bar for quality. A few weeks ago our partnership manager received a media opportunity that looked quite promising, but after reviewing it we realized that it wasn’t going to be worth our time.

Questioning Goals Is Harder Than Mindlessly Pursuing Them—and More Rewarding

Life — personal and business — is full of unknowns. Challenges and tragedies will arise that are beyond our control. Faith in your ability to achieve goals is a great tool for achieving success, but sometimes faith in what will happen if you let go of them is just as valuable.

I still find it quite difficult to not press on when I have set a goal. But I also remind myself of the perils and downfalls of pursuing goals at all costs. In a way, it’s actually easier to plow along mindlessly instead of revisiting objectives or having the humility to acknowledge that our goals were wrongheaded.

As Phil Knight says at the end of his new book, Shoe Dog: A Memoir by the Creator of Nike, “And those who urge entrepreneurs to never give up? Charlatans. Sometimes you have to give up. Sometimes knowing when to give up, when to try something else is genius. Giving up doesn’t mean stopping. Don’t ever stop.”

As for our search for a new home, it took us a few years to come to terms with our disastrous experience in Portugal. But it’s true: time does help heal all wounds. A few years later, we moved to the United Kingdom. The weather may not be as nice, but we’re very happy.

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Sandra Lewis is the founder of Worldwide101, a premium virtual assistant company connecting demanding founders and executives with highly skilled, meticulously matched help. You can connect with her on Twitter or LinkedIn.

Sandra Lewis

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Founder & CEO of

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