Becoming a freelancer has plenty of benefits including independence, freedom, and control over your time. However, it also involves many ups and downs, doubts, and uncertainty along the way. In this episode of Career Relaunch, Stephen Satterfield, a former restaurant manager turned freelance writer and founder of an online food magazine shares his own unique career journey and thoughts on how to patiently manage upheaval and uncertainty in your career. I’ll also address a listener question about how to stay motivated each and every day.

Key Career Insights

  1. Building a new career is like building a business. It requires patience, time, and an ongoing commitment to create the change you desire.
  2. Uncertainty is a common part of career change that people don’t always talk about, but your ability to acknowledge and manage it is critical.
  3. Even if you’re not doing “what you love” full time, taking small steps in that direction still creates progress.

Tweetables to Share

Resources Mentioned

Mental Fuel- Listener Challenge

Mental FuelDuring this episode’s Mental Fuel segment, I shared a few ways I stay motivated even when I’m feeling a bit frustrated. What are some of the techniques or tools you use to stay on track with your own career goals? Share your tips with the Career Relaunch community in the comments below.

About Stephen Satterfield, Food Writer, Activist & Founder

Stephen SatterfieldStephen Satterfield is a food writer, speaker, food activist, and Founder of Whetstone Magazine, where he shares stories of food origins. He’s the inaugural food writing fellow at Civil Eats, a leading voice on the American food system, and the former restaurant manager at Nopa in San Francisco. Follow Stephen on Twitter and Instagram.

Did You Enjoy This Episode? Please Let Us Know!

Comments, Suggestions, or Questions?

If you have any lingering thoughts, questions, or topics you would like covered on future episodes, record a voicemail for me right here. I LOVE hearing from listeners!
Leave Joseph a Voicemail
You can also leave a comment below. Thanks!

Episode Interview Transcript

Teaser (first ~15s): A lot of people feel that, when they’re confronted with the doubt and the anxiety, they’re not equipped for it or that they’re unsure of themselves. I think that uncertainty is completely part of the experience.

Joseph: Stephen, good morning, and thanks so much for joining me here on Career Relaunch.

Stephen: Thank you. I’m really excited to talk to you, Joseph.

Joseph: I know you’ve had a really unique and diverse career in food and beverage and also as a restaurant manager and also as a writer. I’d love to just start off by learning a little bit more about the food writing you’re doing right now.

Stephen: Right now, I am a writer for an online publication called Civil Eats. Civil Eats is one of the foremost authorities on the American food system, particularly around the issue of sustainability. When most people hear that I’m a food writer, what they imagine is me on a budget and going out to fancy restaurants and critiquing fine food and wine, which I’m sorry to disappoint you—it disappoints me as well—but that is not the kind of food writing that I do. I’m more focused on really how the things that we eat and drink arrive to our plates.

Joseph: How long have you been doing writing?

Stephen: I have been a writer my entire life, but this transition has really come to fruition, I would say, over the last three years. Notably at Nopa Restaurant in San Francisco, where I was a manager for five years, I started a very basic Tumblr blog to catalogue all of the amazing things that I was seeing around me every day, beautiful food and many different iterations from arriving from a local farm all the way to the final composition, which just over the years, year by year, turned into a side project to eventually a full-time multimedia project that I was managing called Nopalize, which is basically a spinoff of the restaurant’s name, which I think gave me enough credibility to begin getting offers from more traditional publishers.

Joseph: Before we get into more of your writing, can you just take us back to what you were doing for Nopa and your role there as a restaurant manager? What was your day-to-day life like?

Stephen: A restaurant manager is a pretty thankless job. The hours are quite long. At this restaurant in particular, it is now a 10-year-old, farm-to-table restaurant right in the middle of San Francisco. The volume of the restaurant made it so that, sometimes, a typical day would be arriving at 2:00 p.m. and then locking up at about 4:00 a.m. and getting to bed at about 5:00 a.m. and really even doing a lot of my writing after 4:00 a.m. shifts, into 5:00, 6:00 in the morning, and then crashing and then waking up the following day and doing some version of the same thing.

I really, really strongly identified with the ethos of the restaurant because it was really built to sustain the local food community and to really support sustainable farmers and producers, which are principles and values that I strongly identify with. I was happy to be in the role, but obviously, with hours like that, especially with a bubbling interest of writing, it was really inevitable that I was going to eventually have to move on. I’m just fortunate enough that my employers at that time were so forward-thinking that they really allowed me to explore this new food media platform that really helped catapult my career.

Joseph: I know a lot of people who are interested in either the restaurant industry or they want to be chefs or they want to manage a restaurant, because you see this stuff on TV and on the movies, and it all seems very glamorous. Can you explain to me what your motivations were in moving on?

Stephen: Restaurants, for most people, have a shelf life. It’s a younger person’s sport so to speak because of all the physical demands. There’s always this perpetual negotiation of the money’s really good, I like having the cash, I really love this community, versus I don’t want to be doing this when I’m in my mid to late 30s or mid to late 40s.

For me, I just had such a high regard for Nopa, I just couldn’t really see anywhere else that I would really desire to work in a restaurant after that experience, coupled with the fact that I had a very profound and growing interest in really becoming a storyteller and doing narrative multimedia journalism to try to tell a more honest account of what the life and culture is really like of people who are in the food community.

Joseph: One of the things that I sometimes hear from people, which I think is what you’re describing, is this sort of emerging interest that comes up alongside their full-time job. How did you then begin to think about this passion for storytelling or this passion for writing becoming an actual career for you?

Stephen: As I spent more time paying attention to what was out in the marketplace, I started realizing that not only was I not really seeing anything that reflected exactly the idea that I had, but the ones that approximated it were really clear validations. I think the more that we just paid close attention to the marketplace, the more we felt like there’s a conversation in food that people are ready for that’s not entirely being reflected in the glossy food magazines.

Joseph: You decided that you want to pursue this. What happens next for you in your career here?

Stephen: I decided I wanted to leave the umbrella of the restaurant media project and focus more globally on some of these food issues. I started doing some traveling and this exploration around food origin, food culture, and food ways, really looking at the things that we take for granted. All over the world, there is this collective new interest and consciousness in food culture in a way that is really unprecedented in any other time in history. It just became really clear to myself and some of the people who I’ve been working on the project with that we really needed to be the ones to begin to document this amazing international movement.

Joseph: I’d like to try to shift the conversation a little bit to talking about your career and what this was like for you personally to make this shift. Obviously, you’re creating something from nothing and you’re embarking on pioneering in this new space. Can you describe what it was like for you to leave Nopa behind and to then, suddenly, be traveling around the world capturing these stories?

Stephen: It was, in a way, I feel what I had been training for in a sense. The thing about traveling to these place that really made me feel like I was both connected but also definitely further away is looking at the commonality of the spirit of these farmers and their practices in different parts of the world and then seeing the ways in which they were so familiar to all the farmers that I’d known from California. I think it was really when I was on the farms that I felt, again, just really validated in all of the preparation that I had been doing, kind of unknowingly too, just really out of my own curiosity and just almost understanding this other language of agriculture.

Joseph: One of the questions at the back of my mind is that this does sound like a dream. It sounds amazing to be able to travel around the world and document all these different food practices. How did you fund your travels? How did you make this new life for yourself viable?

Stephen: It is very, very expensive to leave your job and travel the world. Again, I started traveling in the fall, and I knew that I was going to begin that journey in January. A lot of the initial travel, I just paid for through my own savings and out of pocket. We started to do some outreach to people and these communities as we started to hone in on the stories that we wanted to pursue. I think, almost always, our lodging was in someone’s home, and so it wasn’t as if we were staying in really fancy hotels each night.

We specifically chose places that were just inherently inexpensive. We did some filming in Oaxaca, which is gorgeous but also the second-poorest state in Mexico and not at all an expensive place to travel. All of these places that we went were chosen with limited resources in mind. Frankly, we just weren’t really spending a lot of cash.

Joseph: This is really interesting because I know that one of the things that stops people from pursuing their dream is money. How do you think about money right now, now that you’re pursuing this dream of yours?

Stephen: I am emphatically in favor of people having part-time jobs or jobs that provide them supplemental income. I have been fortunate enough to, throughout that time, get work as a freelance writer. As a freelancer, what you quickly realize is that the money that you are owed is not the same as the money that you have. Had I not been in places that were inexpensive and only relying on my freelance income, I would’ve been in a really, really, really sticky situation on more than one occasion. A lot of the clients are not really held accountable for giving you your paycheck in the same fashion that they would have to if you were an employee of theirs.

I think that’s a really critical thing for a lot of people who are pivoting into a new career to understand, because oftentimes, one of the plans about money is, ‘I’ll just do this thing that I’m doing on the side to make a name for myself, to make a little bit of additional income while I start the business.’ That’s fine if you have the ability to live and pursue that project without relying on that freelance income, but if you make the leap and the plan is to rely on freelance work, I would strongly advise against that.

Joseph: What do you think has been the hardest part of being a freelance writer?

Stephen: It’s absolutely the money because what no one tells you is that you really do spend a great deal of time just sort of tracking down your money. It’s really much easier to be zen about the whole thing when you’re not relying on that money to, let’s say, pay for rent.

I just think for any young writer, it’s not the advice that they want to hear, but until you get to a point where people are contacting you, you probably want to keep your day job if you want to be a writer, because unfortunately, the writers are getting paid a little bit less because there are so many people who are willing to do the work for relatively little money.

Joseph: Has there been anything else, Stephen, that you have found to be surprising, specifically related to the move from being a restaurant manager to more of a food writer?

Stephen: It’s very lonely. I think that was the biggest surprise for me: a lot of people who work in restaurants are very social, very gregarious, outgoing people, and the life of anyone who’s starting anything is really lonely. It requires a lot of hours of intense concentration, quiet, and focus and solitude, especially as I was working from home to get a lot of this started. Your proximity to the fridge is just a couple of steps away all day long. If your brain wanders for even a second, ‘Am I hungry?’ then yeah, you’re hungry, and you’re up and moving around.

Just the ways that you have to fend against your own distractions of other people, you also have to recognize that it is going to be lonely sometimes, and you’ll need to schedule time for socialization so that you don’t really get too bummed out in solitude.

Joseph: Is there anything else that you miss about your former life or your former career as a restaurant manager now, looking back?

Stephen: I miss the people. They call it the hospitality industry, I think, rightfully so. It’s really for the people who inherently are hospitable or who really buy into that notion. It’s almost like just having one grand dinner party every single night. Again, for me, the most stressful part of running the restaurant were always everything leading up to opening the doors. Once the doors were opening, it was a show. That adrenaline that you get from being the conductor of that big show, that I kind of miss.

I really think it’s important that people don’t have this notion that, ‘Unless I’m making 100% of my income from this one thing, I’m failing or I’m not doing it right.’ I really think that’s misguided, and I think that that, a lot of times, just comes from purely a place of ego. Perhaps use it as motivation to get yourself to wherever you want to be, but just try and go zero to a hundred from one job into a full-time career switch, it’s just really a risky proposition and frankly a more difficult proposition. If you are able to have a part-time job, it actually keeps you more productive.

Joseph: What do you think prevents people from taking part-time jobs to supplement their income?

Stephen: I think a lot of times, people just feel some sort of failure or inadequacy, like it doesn’t feel real or substantial if they’re not doing it all on their own or all their way. The reality is there isn’t such thing as an overnight success. That’s not a thing that happens very often. You’re better off trying to play the lottery if your plan is to make it happen overnight. What’s way more likely in any business venture is that it’s the product of day after day, month after month, compounding year after year, until there is a significant breakthrough.

If you look at your own, let’s say, hobby or freelance career or aspiration in the same way, or career change even, what you have to understand is that you’re building your new career in the same way you would be building a new business. You have to have that same patience with the process. Just like if you were starting a new business, you would have to take on loan from an investor or a bank until you could pay them off.

It’s really no different for freelancers. You might have to take the investment income of, say, a part-time job. After three years, just like you would have paid your investors back, maybe after three years of your part-time job and your diligent work on the side, you can leave that job. You can leave it with a great deal of pride because you’ll be leaving, and you’ll know that you’re in a position in which you have saved and earned and built your business or your career to a point where you can comfortably leave. I think there’s so much more gratification in that.

Actually, a big hindrance for people starting their own thing is that they just feel, ‘I can’t really start it until I can do it full-time.’ That gap is just so large that you’ll get swallowed up in that chasm before you even begin if that’s how you’re looking at it.

Joseph: Can I go back to one of the things you’re talking about earlier, Stephen, which was the loneliness period or not having the people around you who you used to have around you. What keeps you going during those lonely times?

Stephen: Once when I got lonely, actually when my partner was traveling in Europe for a couple of months, I spent I think about three or four months doing dinner parties each week. That became this incredible opportunity for me to always have something on the calendar, to look forward to. There’ll be a new cast of people each time. It did so much to strengthen the relationships that I already had here, to bring in new relationships, to make me a better cook. If you do have a community or an interest in being a part of a community, I would say just looking for these recurring gatherings that other people are hosting or maybe even hosting yourself is a really good way.

Joseph: I was reading your last blog post on Nopalize. One of the things that you mentioned that you learned was that upheaval is never easy but always necessary. What did you mean by that?

Stephen: About twice each decade, there is a necessary moment in which the work that I have been doing up to that point gets to be comfortable. I think as soon as your work becomes comfortable and familiar, you have to move on to the next thing. That upheaval is really difficult because it’s like the alarm clock going off. When you’re in full-on REM sleep and you got the blankets on and it’s cold and you got nice wool socks, the last thing you want to do is enter into the cold. I think every five years or so, we are in these peak moments of slumber that need to be reinvigorated, reawakened and redefined.

Joseph: Speaking of your own career change, when you look back on it, was there something that you felt you learned about yourself?

Stephen: The main thing that I learned about myself is that I am really fragile. I think it’s an important thing for people who are entrepreneurial or starting new ventures to articulate. There’s a lot of people who give advice who are entrepreneurs who talk about grit and toughness and perseverance and all those qualities that are absolutely necessary.

It is also true that there are moments where you have to be tender with yourself and there’s a self-awareness that is really important to where, after a hard day, you can say like, ‘I really did get my ass kicked today,’ or, ‘I don’t know if I can do this. I have real doubts.’ Being able to fully absolve those moments as part of who I am and part of this experience and then being able to move forward the next day with the same resolve everyone talks about, I think that’s really the key, because everyone who talks about their boldness and courage and perseverance, they all have doubts as well.

This is very difficult stuff to make big changes in your career, in your life. A lot of people feel that when they’re confronted with the doubt and the anxiety, they’re not equipped for it or they’re unsure of themselves. I think that uncertainty is completely part of the experience. It’s as much a part of the experience as the courage and the toughness and the grit. Unfortunately, people don’t talk about it as much.

I didn’t graduate from college. I know we didn’t get into my entire backstory, but I went to culinary school and just started in a professional track as a food and beverage and hospitality professional. Especially for me, I had so much insecurity about being a real writer or not having a journalism degree. There’s so much doubt, but the more productive I was in my own work, then the more I realized being a writer is just about writing. My output, frequency, and quality is just as good as some of these other people, and so I was emboldened to move forward despite that insecurity.

Joseph: I think that’s a great reminder. I can tell you, as a small business owner myself, I definitely feel like there’s always this pressure almost to come across a certain way or to act like you’ve got everything together and everything’s working. The reality is that there are a lot of days when things don’t work. There are a lot of down moments, and there are a lot of moments that are really frustrating.

My final question to you, Stephen, before we move on to your current project, is what’s the best career advice you could offer to people who are thinking about making a career change?

Stephen: Once you have identified something that you’re better at than most people or something that you enjoy doing or can do without realizing that you’re working, find the people who are doing those things at the highest level and just copy them. Look at their work as a literal blueprint and go from there.

Joseph: I can’t let you go without talking a little bit about your current project, which I understand is a multimedia project about food origins. Can you tell us a little bit about that?

Stephen: I am working on a multimedia publication called Whetstone Magazine. Whetstone is basically a continuation of a lot of the work that I’d described at Nopalize – exploring food origins and culture. You’re able to check it out on or also just at Whetstone. If you want to learn more about the local food communities and cultures from different pockets of the world, then follow us there.

Joseph: Final question for, was there something in particular you came to appreciate about food while you’re capturing these stories of food origins?

Stephen: All that wholesomeness that happens around the table in our best moments as humans and as families and as neighbors, that is a very beautiful universal language. It’s always been part of an ideal that I’ve had about the power of food. That connected quality that we have around food or at the dinner table is truly one of the few shared languages of all human beings.

Joseph: Thanks so much, Stephen, for taking us on your career journey in the world of food, your experiences as a freelancer, and sharing some tips on how to identify your passion. I hope everything goes well for you with Whetstone. Thanks so much for your time.

Stephen: All right. You as well, Joseph. Thank you. I appreciate it.

About Joseph Liu

Joseph Liu is dedicated to helping people relaunch their careers and do more meaningful work. As a public speaker, career consultant, and host of the Career Relaunch® podcast, he shares insights from his decade of experience relaunching global consumer brands to help professionals to more effectively market their personal brands.

About Joseph Liu

Joseph Liu helps aspiring professionals relaunch their careers to do work that matters. As a keynote speaker, career & personal branding consultant, and host of the Career Relaunch podcast, his passion is helping people gain the clarity, confidence, and courage to pursue truly meaningful careers. Having gone through three major career changes himself, he now shares insights from building & relaunching global consumer brands to empower professionals and business owners to build & relaunch their personal brands.