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NOTE: Five years ago, I left a 15-year career in advertising to work for myself in an entirely new field. Recently, I solicited questions about this for people who are considering the same. This post is part of a series where I'll be answering some of those questions. In many cases, I've combined questions that were similar.


Hi Laura,

I am at the point where I am ready to leave my successful career that has been good to me up until now. Very good, in most respects. I’m a Director of Accounting at an up-and-coming virtual accounting firm, creating jobs for many people to get their start in this career, and a 45-year-old mom of two college-aged kids. My career enabled me to make life happen for myself & two kids, including their college educations. Accounting was a very reasonable choice for me; I’ve always been very good at it & also very non-passionate about it.

What I am & always have been passionate about is healthy living, cooking up a vegan storm, feeding others (especially by way of soups!), breaking bread together with all kinds of people, and (most recently) starting an organic produce & flower farm with my partner & his brother. All signs are screaming at me to just make the final jump & pour myself into an organic café/farm/wellness experience to offer others. Nothing excites me more, and I can see all kinds of worlds opening up from that – such as creating a cookbook, offering children’s gardening programs for local schools, perhaps finally learning how to create beautiful pottery & combining that with the café, etc.

My question to you is: how did you find the strength to leave behind a steady, high salary to venture into what might be even failure? How much of a nest egg did you have (assuming you had one) that gave you enough comfort to make the leap? Did you downsize your life, or was trust in the universe what made this work for you?

Thanks again, for all you do,
All Signs are Screaming


Dear All Signs are Screaming,

One thing that has helped me many times in big decisions is to think from the end. I imagine getting to the end of my life with a particular outcome and I see how the reality of that outcome hits my heart.

For example, when I was struggling to get sober I would imagine getting to the end of my life and never having got there. As in, still drinking. The idea was unfathomable—more unfathomable than the unfathomable idea of never drinking again. It just wasn’t going to be my story.

I went through the same process when evaluating relationships (Could I imagine this being the relationship I stayed in for life?). I definitely did this with my dream of becoming an author (Could I imagine getting to the end without having at least tried for it?).

Framing things this way has always pointed me to the bottom line truth. It’s a real perspective sharpener, because the reality is, of course: we don’t know when the end will be! As my friend Jim says, we don’t really know if we are old or young, it all depends on how much time we have left. Oftentimes, we delay and delay and delay these kinds of decisions as if we have infinite time, but we don't.

The real reason this line of thinking works is because it’s not about thinking at all. When you consider your life choices from this end, it hits you differently. Your soul gets involved. And, if only for one glorious moment, you stop thinking.

Our minds are useful. They solve problems and allow us to drive cars and make lunches and do all kinds of complicated, wonderful stuff. But they are largely prediction machines. They have magnificently, efficiently evolved to predict what will happen next based on what has happened in the past. This is great when it comes to something like driving a car, but horrible when it comes to making big, courageous leaps into the unknown (like starting an organic produce and flower farm after being in accounting for 25 years). Your brain has no if/then scenarios built on this yet. It doesn’t have any data to work with. So, mostly, it screams Stop. Danger. No go. At the very least, it works to build out A Very Safe Project Plan for how you might go about this. And there’s nothing necessarily wrong with that. Planning is not a bad thing. It’s just not the place from where big, bold moves are made.

These kinds of moves—or strength, as you put it—come from somewhere else. They come from the place inside you that wrote, “Nothing excites me more, and I can see all kinds of worlds opening up from that…”. That’s your soul talking. Your dharma, in yogic terms. Your truth. It’s your Bigger Yes, as I like to call it. People might roll their eyes at that kind of talk, but fuck ‘em. Let them eye roll all day long while you go about the business of creating more joy and meaning in your work and life. Let them roll their eyes as you serve your community those delicious soups and beautiful programs.

In my last letter, I wrote about the importance of starting to do the things you dream of doing before you make the move to doing them as a job or career. You’re already doing that, it seems. Your kids are grown up, which is definitely a plus. You’re familiar with bookkeeping and finances. You mentioned a partner that wants to embark on this adventure with you, or is at least supportive of it. And you say that all signs are screaming go. I don’t know the particulars of your life, but these factors alone are so much more than most people have working in their favor!

The Myth of One-Sided Risk

The part of your letter that stood out most to me was this: How did you find the strength to leave behind a steady, high salary to venture into what might be even failure?

You realize there’s a risk of failure either way, right? Staying with what you know and that steady paycheck, although it may feel safe, is risky as well. My experience is that our unused potential is not benign. When we don’t step into it or pursue it or however you want to put it, it doesn’t just dissolve. Instead, it turns into something dark and destructive and clawing. We know it when we see it in other people: it takes the shape of depression, bitterness, and regret. Much of the pain of my addiction came from this place. Alcohol was certainly killing me, but not living into my potential was slaughtering my spirit. It haunted me every single day.

I’m not saying this is what it will be like for you. Only you know how this idea sits inside of you, how important it is. But I want to make it clear that both choices have risk. Both have the potential for failure. The question is, which kind of failure can you live with at the end of the day? Would you rather try at this thing and fail, or never try, and not know? It’s a question you have to answer honestly, and only for yourself.

Another way to look at it: there are so many people who don’t have the means, the health, the support, or the resources to even consider doing something like this. So my view is, if you can, you must. When we show up fully in our lives, when we courageously accept the adventures that call to us individually (and this is clearly something that has been calling to you), the end result is always this: service. We are in service to those around us. I don’t have any desire to do what it is you want to do—it’s not my thing—but you do! Why? Because it’s where your gifts can best be of service. That's my take, at least.

The Practical Side

You asked about a nest egg. I had enough money to survive for 6-9 months and no savings beyond that. I had no credit, six figure debt, and was a single mom to a five year-old. That said, her dad was financially stable and I knew would be able to step in if I couldn’t pay for things for her, if it came to that. I live in Massachusetts, which offers affordable state-subsidized health care, and I had no major or even minor health issues to consider. I lived in a small apartment, so there was nothing to downsize there. I put my student loans on forbearance. My car payment was pretty small, but my car insurance payment was massive because of my DUI.

I’m including these details because they were asked by others, and I think it’s important to paint an accurate picture.

The amount of money I had was comfortable enough for me (everyone is different). The only other thing I needed to feel okay taking the leap was for my ex-husband, my daughter’s dad, to be on board. I needed this because he could make my life very difficult (not that he did) and his support—or at least the lack of his disdain—was important to me. Luckily, he was supportive. I was able to shrug off any other naysayers.

The Relative Nature of Failure

I think the number one reason I felt like I could do it is because I had gotten sober. I’d already been through my own personal hell and crawled out. This meant a couple of things. First, my tolerance for difficulty and failure was pretty high. Worst case scenario, if it didn’t work out after a year, I’d go back to working at a marketing agency. While the idea of this was about as appealing as eating dog shit, it’s not like I was going to be homeless. I knew if I was sober, I’d figure it out. Second, I just wasn’t messing around anymore. I didn’t get sober to play small—I’d already done enough of that. For me, not playing small meant taking the leap.

I love your letter. I could feel all the excitement and joy that people have when they talk about doing something they love. I personally hope you do it, if only so you can say that you tried. If you were looking for permission, I hope you got it. If you were looking to become unafraid, I can tell you that nobody will be able to give you that. I've talked to people that have years of savings, and even people who don't have to worry about money at all, and they still couldn't keep themselves from worrying about all the ways a big move could go wrong. They just couldn't get comfortable enough.

Don't Wait for Comfort

The truth is, in my experience, we have to do it afraid. That's the whole point. Pema Chödrön says, "Fear is a natural reaction to moving closer to the truth" and that's been true for me all the way through. All the best things in my life have terrified me: parenting, getting sober, writing a book, being in love. So don't wait to be unafraid or comfortable; it won't happen. Ask yourself instead, What are you unwilling to leave out of your story?

Listen to the answer and then, leap.


Photo by Etienne Girardet on Unsplash

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