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Published: Oct 01, 2019 7 min read
Courtesy of Jamie Lieberman

As an attorney, saying no is second nature to me. But before I pat myself on the back for maintaining excellent boundaries, there is an important caveat to that statement. For a very long time, this skill only extended to work done on behalf of a client. When it came to saying no and setting boundaries for myself, I just couldn’t do it.

When you have a career, hobbies, volunteer work, family time, and wish to maintain some time for yourself, saying no is a must. I learned this lesson the hard way when I found myself running my own business, raising two children, and attempting to carve out time in the day to hit the gym or meet a friend for coffee. Without having the ability to slow down time, I found myself constantly exhausted and sacrificing my own time to accommodate everyone else. Sound familiar?

In a comic moment where I had somehow double booked two phone calls and committed myself to volunteer at my son’s school, I made the desperate and radical decision that I would say no to every single request or opportunity that was presented to me for the rest of the day. It was liberating. It also made me realize that it was time to focus my energies on setting boundaries and saying no.

Breaking the “yes” habit is far harder than it seems. But it is possible. I use the following steps when evaluating every opportunity, from speaking engagements to meeting a friend for coffee.

1. When approached with a new opportunity, the default answer is always no.

Sounds crazy, right? Before we get into this step though, please, don’t start saying “no” out loud. Instead, make this your mental default answer. By starting at no, it forces you to take the time to evaluate what is being presented. Since you aren’t blurting out “NO!” try this response instead, “This sounds really interesting. I’d like to review my current commitments to make sure I can devote the time needed. Can I get back to you in a few days?”

Remember — each opportunity you have, no matter how exciting, will take time away from the pile of promises you’ve already made. In evaluating new offers, consider not only the benefits, but where you’ll find the time and what other commitment you already have that may suffer. Which leads me to my next step…

2. Ask all the questions.

Convince yourself of why you should say yes. List out the questions you need answered before you can finalize your decision. Challenge yourself to not only consider the benefits but also the potential pitfalls.

Ask yourself questions such as:

  • “Where does this fit in my existing schedule?”
  • “Does this really excite me?”
  • “If my friend was in my shoes and she was presented with this opportunity, would I tell her to accept it?”

And the most important one: “Do I actually want to do this?”

Carve out ten minutes to sit and do this exercise alone, potentially in a journal. Since you aren’t sharing your answers with anyone, it gives you the space to be honest with yourself about your answers.

3. Listen to your gut.

The nice thing about not responding immediately to an opportunity is that it gives you time away from it.

When you clear your mind and take the emotional aspects out of the decision, you will be able to clearly hear your inner voice. Deep down, you likely already know whether you should say yes. You just need to clear your head long enough to listen to your instincts.

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4. Understand why you feel compelled to say yes.

At this stage, you may have already realized that you need to say no. But you may still be wavering. To truly feel confident in saying no, you must understand why it is a challenge for you.

It is not one-size-fits-all. Your reason is likely very different than your best friend’s or your colleague’s. It takes a tough look (and sometimes some tough self-love) to understand how our emotional make-up plays in learning to say no and setting boundaries.

5. Say no with grace.

You have followed the steps. You know you need to say no. You are so ready! But now what?

How do you actually tell your boss you can’t take on a new project? Or your mom you’re unable to attend brunch on Sunday with your cousin?

Saying no should not consist of long-winded explanation with apologies. Instead, keep your message short and direct. The following formula usually works well.

First, lead with a message of gratitude. It can be as simple as “Thank you for thinking of me in connection with this opportunity.”

Next, include a statement that is specific to what was presented. “The chance to have lunch with cousin Judy sounds like so much fun!”

Finally, end with your regrets. “Unfortunately, I won’t be able to attend, but I would love if you kept me in mind for future lunch dates.”

Reprogramming your brain to say no with confidence takes time and practice.

Just last week, I managed to overbook myself without realizing what I was doing. Note to self: you cannot record a podcast and take a gym class at the same time.

But now I can laugh when it does happen because I know I have a good framework in place when I need to reset and reclaim my schedule. And you can too. Because no one wants to hear a podcast interview with someone running on a treadmill.

Jamie Lieberman, owner and founder of Hashtag Legal, has been a practicing lawyer for nearly 15 years. As an experienced entrepreneur, Jamie understands the unique needs of business owners at different stages in their organization’s growth. Today, she partners with clients across verticals including influencer marketing, creative services and e-commerce. She has a deep commitment to making legal accessible and regularly speaks about legal matters, the art of negotiation and entrepreneurial topics at leading industry events such as Alt Summit, Podcast Movement, and FinCon and as an expert source for media like Digiday and Forbes. You can also catch her as a co-host on The FearLess Business Podcast.