You may think, since I no longer practice law, that I lead this idyllic life and never struggle with shit. Particularly since I’m a career and life coach. Let me let you in on a secret: I struggle all the time! I struggle especially when it comes to things that sound or look right, but my gut says “No Way, No How.”

If you're not saying no to things that make you feel boxed in, you're doing it wrong. Crawl out of your box and into freedom.
If you’re not saying no to things that make you feel boxed in, you’re doing it wrong. Crawl out of your box and into freedom.

I was asked to be part of a new group forming in my area, whose purpose is to help give women in transition the tools they need to empower them. Sounds right up my alley, right? Of course it does. So I went to an organizational meeting. We decided to have a big, brainstorming, white-boardy meeting this month, to flesh out ideas, put a schedule together, etc.

The closer the date got, the more I felt myself not wanting to go. I didn’t move a client call that conflicted with the meeting. I started fixating on what I didn’t like about some of the people involved. I started rationalizing that I really needed to go to they gym regularly, and this group’s schedule conflicts with my gym time.

But part of me kept on: What is wrong with you? This is a great opportunity to make a difference! You need to get out and meet more people, this is perfect! And, I felt guilty because I’d made a commitment. Plus, I really like the woman who asked me to be part of it, even though she does financial services and I usually have a severe allergy to people who focus on money for a living. She had in fact said to me, “We really need you. We need someone with your skills.”

Well, trust me, flattery can get you pretty damned far with me. I become a total sucker when people admire my work. And if the flattery doesn’t work, telling me you have a need I can help you with will definitely hook me. Yep, I’m totally manipulated by helping and pleasing people.

Yet the internal debate raged on. Finally, I pulled out a tool that I use with clients all the time: Which feels more like freedom, going or not going?

What Freedom Is—and Isn’t

Now I know, from working with clients, that lawyers often misinterpret what freedom is. Here’s a great explanation, courtesy of Martha Beck in Steering by Starlight:

The Buddha often said that wherever you find water, you can tell if it’s the ocean because the ocean always tastes of salt. By the same token, anywhere you find enlightenment—whatever improbable or unfamiliar shape it may have assumed—you can tell it’s enlightenment because enlightenment always tastes of freedom. Not comfort. Not ease. Freedom.

Lawyers often confuse freedom with safety and security. Freedom is not either of those things. It’s a feeling of exhiliration, maybe even edged with a little fear. You’ll know it’s freedom because it doesn’t feel like imprisonment. So often, lawyers feel they must keep that safe job, especially in this economy. But if they picture themselves leaving, whether they intend to or not, they nearly always tell me that it’s like a weight rolls off them. That weight is the weight of imprisonment.

So when I asked myself what felt more like freedom, the answer was very clear: Not going. I felt energized by that thought. When I thought about going, I felt weighed down and boxed in.

Freedom for Introverts

It has taken me a while to get comfortable with this tool. Partly, that’s because my introverted self tends to dread, if not loathe, going to stuff that involves people I don’t know fairly well. I know from experience that sometimes, if I just push myself a little, I’ll have a lovely time and be glad I went.

But, going to events is often just draining. Sometimes the drain is minor, sometimes it’s major. The level of drain depends not only on the event itself, but what else is going on in my life. If I’ve had a heavy client week, I promise you that even going to a really fantastic event will be a struggle, and the chances are good I won’t make it unless it’s super important to me.

I used to think this aversion had to do with depression. But the more I learn about introverts and the level of stimulation they can tolerate, the more I see that going to a Friday night happy hour was a sure-fire recipe for needing days of quiet time to recover. Which, as a young associate, I often didn’t get, seeing as I had to show up on the weekends to work. I may not have had to interact with people, but that was not restorative time, to put it mildly.

It’s OK To Please Yourself First

Sure, by bowing out of this group I will disappoint people. Some of them, including my acquaintance who invited me, may think less of me. I don’t love that thought. Part of me feels ashamed that I can’t just suck it up. Or rather, that I’m consciously choosing not to suck it up. After all, I spent a long time learning that sucking it up was the path to success. It took me a while to discern that the success it garnered me benefitted other people a lot more than it did me.

It’s very clear that for whatever reason, this group is not the right path for me, at least for now. I can’t articulate exactly why, either. Maybe the Universe knows I’ll need that extra time and energy for something else. Maybe there’s some negativity to this venture that I can’t discern. The maddening thing is, the chances are good I’ll never know exactly why, at least for a good long while. And I might just be wrong. This is as much about practicing faith in my own gut as anything else.

Despite all this uncertainty, I’m bowing out. I’ll tell as much truth as I can about why, but I’ll probably omit the part about how I’d rather work on crocheted flowers than participate in this group. Crocheting flowers feel healing, and fun. To most people, they sound frivolous, and I know that I would get judged. I don’t care a whole lot about that, but I also have learned that placing a target on my chest isn’t a great strategy, either. There’s vulnerability, and then there’s stuff that people haven’t earned the right to hear yet.

So for all of you pleasers out there, and for those who always choose the thing that looks good, I recommend this freedom test as a tool to use often. Even though some people may think your decisions don’t make sense, that’s their problem. What I can tell you is that this tool hasn’t led me astray yet.

Jennifer Alvey is a recovering lawyer who dumped the punch-list lifestyle when the years still started with a 19. If you’d like help doing that in your own life, contact her at to schedule a discounted sample session.