The Side Hustle and Flow Interview Series: Laurie Gay

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The Side Hustle and Flow Interview Series is designed to inspire hard-working corporate employees to either start a side hustle if they are interested in eventually starting a business, or to keep going with their existing side hustle through the inevitable challenge of limited time and energy.

So far we have profiled Chandoo, Willie Jackson and Dan Schawbel.

Today, we talk to lawyer-turned-coach Laurie Gay.

What was your former day job?

I used to be an attorney. I worked as an associate for a large law firm in Manhattan called Simpson, Thacher and Bartlett.

What was your side hustle?

My side hustle was helping people change their relationship with food to enjoy food at their lowest natural weight, and helping people who feel really lost in their careers figure out what to do to be most fulfilled.

When did you start working on it?

I officially started working on it back in September 2008.

Did you tell your employer you were working on a side project? Why or why not?

No way, Jose, did I tell my employer. I didn’t tell anyone until I it came time for me to quit — but, I also didn’t charge money for anything until I quit, too.

I coached for free because having a side business might have violated my employment contract, and I wasn’t willing to risk being fired. Also, ethically speaking, I felt uncomfortable going against something I’d agreed to comply with when I started working there. But this is a personal decision; another person might come to a different conclusion.

I still told no one, though, both because (1) I felt incredibly self-conscious about doing something connected with “feelings” and being “happy” (heaven forbid!) and (2) significant side commitments are not exactly encouraged at my old firm.

The thing is, the partners (who were all basically my boss) certainly want associates to be happy — the partners are actually very nice people… for the most part. They understand that outside interests are part of living a good life. But the reality is, at the end of the day, my old firm is so successful because the attorneys provide around-the-clock service for all of their clients. That kind of constant availability to work means irregular hours, and long hours, and neither of those gel with side hustling.

How did you know when it was time to quit your day job?

I knew it was time to quit when work started getting so busy that I had no regular early mornings free to do my coaching on the side.

I also knew it was time because I had also done all of the preparation I had set out to do: I had created my website, practiced coaching for 9 months, and saved money. I was also insanely burnt out, and staying at the firm for much longer meant risking damage to my reputation as an attorney. I had worked way too hard to risk that.

What scared you about that decision?

Um, that would be EVERYTHING about the decision scared me. I was completely terrified about quitting because I’d never taken one step off of the traditional path, ever, in entire my life.

I worried about what my co-workers would think; I worried about my side hustle failing; I worried about not being able to return to practicing law, which was my back up plan, in the event that I needed more money than my coaching business provided.

You name it, and it freaked me out.

What helped me tame my avalanche of fears, more than anything else, was finding examples of people who had lived through exactly what I was afraid of, and not only came out okay, but seem to be thriving.

It also helped to think through my fears, logically, and create a plan in the event that they really happened.

I always came to the same conclusion when I thought it all through: I was following my passion by starting this coaching business, and that even if things fell apart, I would not regret this decision that was made from my heart (and thought through thoroughly).

How did it turn out?

I’m still hustling! I am coaching full time still, and it’s been about a year and half since I left my firm. That, for me, is a huge victory.

I will say, though, that it’s been nothing like I thought it would be. Between working through the fears and unexpected obstacles that come with running my own business and making consistent profits, doing this has been SO much more difficult than I imagined.

If I had it to do it all over again, I would have switched to a less demanding job as an attorney years ago. A more regular schedule would have permitted me to do more to get the ball rolling while I continued to work for a paycheck.

I do, however, admit that I would have hated to hear that particular advice while I was still working, but it’s proven absolutely true for me and so many of my clients: the more you can immerse yourself in your side hustle before quitting, the better off you’re going to be when you leave your job. There are key pieces of what you want to do that you have no way of predicting. Those unexpected pieces of your side hustle, that you can only discover through actually doing it, feel scary at first, but you get used to going with the flow. Work this dance out as much as possible before going out on your own.

What are you doing now?

I’m working, full-time, in my coaching business! I love it. It’s great, I’m learning to let it grow and change as I learn what works, and what’s not right for my clients. Running your own business means getting to know yourself far better than you ever have before. Opening your eyes to your own strengths and weaknesses, and taking care of your business like you’d take care of a child, is all really personal stuff. It’s very fun and fascinating.

What advice would you give for others who are working on a side hustle now that you have a bit of distance?

Test your side hustle out as much as possible before quitting your job!

Ideally, you’ll be making some consistent money before you leave. There will almost definitely be reformulation as you go, and that’s not easier to do without a day job (I swear). I hear people say that if they had more time, they would be able to focus more on working on their side hustle and it would be growing faster/better. That may be true, technically, but if more time for your side hustle also means no job, that also puts a different kind of pressure — financial pressure, among others — on your baby business. The bottom line is that the obstacles without a job are just different, not easier or better or worse.

That said, don’t wait until you’re absolutely drained and in utter misery before leaving your job! If your job is draining your energy dry, find another job or take a sabbatical, because it’s nearly impossible to think clearly when you’re worn all of the way down. Your side hustle will tank as your energy tanks, too.

How can people find you, or hire you?

People can check me out at, and shoot me an email: laurie (at) lauriegay (dot) com to hire me. Feel free to ask me any questions at all!

I work one-on-one, teach classes, and I’ll have a new product for people, too, coming out later this month. And in case you skimmed at the top — I help people have a healthy relationship with food (to enjoy it at your lowest natural weight) and find work that is fulfilling when they are lost. 🙂

Thanks so much for your open and honest description of the side hustle path to entrepreneurship Laurie! Your clients are so glad that you got out of the life of churning for hours late at night at your Manhattan law firm.

Find Laurie on Twitter @LaurieGay.

And in a trivia point for long-time blog and book readers, Laurie’s picture was taken by my favorite wedding photographer Sergio, who I profiled in Chapter Ten. I love bringing talented people together. 🙂

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17 Responses to “The Side Hustle and Flow Interview Series: Laurie Gay”

  1. […] the advice you’re providing is directly related to your profession or your side hustle, then be upfront and acknowledge you’ll need to put together an agreement to make sure […]

  2. […] The Side Hustle and Flow Interview Series is designed to inspire hard-working corporate employees to either start a side hustle if they are interested in eventually starting a business, or to keep going with their existing side hustle through the inevitable challenge of limited time and energy.So far we have profiled Chandoo, Willie Jackson and […] Original post […]

  3. Alexandra Rivera says:

    Laurie your story is perfect … I’m in the stage of reading, questioning, and saving money for what later would be my dream come true. You are an example in the life of everyone. How good you are doing what you love.

    • Laurie says:

      Hi Alexandra! First of all — GOOD FOR YOU! Good for you for taking such good care of your well-being by planning for your dreams. That’s not easy, and you’re doing it. Way to go.

      Second of all — thanks! I appreciate the support. 🙂

      xoxo Laurie

  4. Laurie certainly has a good story to tell. Its always nice to hear about people following their passions.

    • Laurie says:

      Thanks, Robert — I feel the same way. I never knew how terrifying it was to follow your passion (though exciting and wonderful, too — but freaking scary!) and have so much admiration for anyone who takes that risk.

      Looks like you have, too. 😉

  5. Kevin Kuzia says:

    This one is my fave of the side hustle series, thus far… but it could be because I am also an attorney by training, so I can certainly appreciate everything she went through. I think Laurie makes a very good point on taking into account how your employer will view any side business. I will confess that my point of view on this is strongly influenced by the fact I am my company’s ethics officer and it’s a pretty clear part of our code of ethics that any side work be disclosed and approved. Nice to see people do take this serious, as in Laurie’s case.

    Great success story for her – so glad she is doing well!

  6. Heidi says:

    Awesome post! Though with Laurie, I would expect nothing less 🙂

    Excellent point about the benefits of a day job, though I especially identify with the advice of not waiting until you’re completely burned out; that’s where I was with my last day job, and I was so drained and unhappy, I couldn’t get ANY work done on my side hustle (despite the fact that the job itself technically allowed loads of time for working on said hustle). I finally quit that job, to get a different day job, and the difference it’s made in my energy levels is amazing!

    • Laurie says:

      Aw, thanks. (blushing)

      That’s exciting that you’re in such a better job for you now — and goes to show that you’re always the perfect authority on YOU.

      You’re side hustle is fabulous, by the way — I love what you do, miss. xox

  7. […] generously posted an interview with me. I talk about how I got my start — and making that change was […]

  8. Glad to see someone being honest about how difficult it is!

    • Laurie says:

      Thanks, Andy! It really is extremely difficult — I guess it needs to be to end up being successful (or it has for me). I’ve learned a LOT more than I would’ve had I just knocked it out of the park off the bat (so to speak).

  9. Great post Laurie (Pam??)! I’ve been in a slump this morning and this was just the boost I needed. My side hustle is going and I have a day job, but feeling blah about the day job. After hearing your perspective, I’m seeing what a great gig it is – steady income, normal hours, and the ability to grow my side hustle. Yay! And my employer actually knows I have a side hustle, and they have no problem w/it. Feeling grateful, come to think of it. Merci Bien!

    • Laurie says:

      Hooray for trolling the internet as way to de-slump. I have to say, since I do actually know you :), that I’m EXTREMELY proud of the way you’ve handled your side-hustle. You’ve done an amazing job of making the right choices for you, and listening to your instincts — and staying flexible.

      Your, Carrie, are awesome. Even when it’s Earnings Season. 😉