Reflecting on 1 Year of Taking A Side-Hustle To A Full-Time Job

The 20 best questions from GNI readers, answered by Alisha Ramos

It’s been one full year since I decided to quit my salaried job to focus on building Girls’ Night In full time.

GNI teammates at our “GNI Live“ event in April at The Wing D.C.

To mark the milestone, I asked our readers for their best questions for me about the journey so far. Part of my motivation in doing so is to peel back the curtain a bit to show what realistically happens behind the scenes. Another is that while a “side-hustle to full-time job” sounds like a dream scenario, it doesn’t often come so easily and isn’t the glamorous lifestyle many expect. :) I hope the reflections and advice below can serve as both fuel and a dose of reality to any aspiring entrepreneurs out there.

Before you go on, I’d like to stop and thank the entire GNI team for helping make this thing a reality. I’m lucky to work with a lot of talented people who keep me sane and keep GNI afloat. They deserve a shout-out from the top: Tyler Calder, Leah Reidy, Olivia Rogine, Corey Speisman, Eunice Bae, Cara Friedman, Tizzy Brown, Jordan Metzman, and our entire book club host community across the United States and Canada. And you.

REFLECTIONS ON MAKING THE JUMP

1. When you were deciding to quit a salaried job to start your own business, what was the final tipping point that convinced you to go for it? Was there someone that encouraged you, a certain event that sparked it, or were you just listening to your intuition?
   Two things. First, working on Girls’ Night In as a side hustle became unsustainable and I caught myself talking the talk of “self care” but not walking the walk. Producing a newsletter is, believe it or not, a lot of work. I was barely getting any sleep.
   Second, it was the momentum I saw in our audience growth coupled with the fact that I had at least 6 months of savings in my bank account. I think the advice “just take the leap and go for it” is terrible advice, unless you have a financial safety net like family that can support you or have an outside investment. Be realistic, take a look at your finances, and make sure you have a business model that can generate revenue. Are you creating something people want and will pay for? Those are the business 101 fundamentals that are often forgotten in today’s glamorous portrayals of entrepreneurship.
2. What was the best moment of the last year? The lowest?
   There was one month where three separate people came up to me after spotting my GNI tote bag to mention how much they love the newsletter, community, and mission, and some shared their personal stories of making more time for themselves or meeting new friends through the community. I love seeing our mission come to life like that, and interacting with our members offline is the coolest, and sometimes surreal.
   I can’t quite pinpoint the lowest point of the last year. I think with any business, there is a level of uncertainty about the future. You’re building something new out of nothing. I’ve learned that being an entrepreneur is about being incredibly optimistic but tempering that with some underlying level of anxiety.
3. Reflecting back, do you feel like the later part of your 20s was the best time to start GNI? Besides having more time to earn money by having a salaried job, what life experiences contributed to you taking the plunge to start GNI that you wouldn’t have had in your earlier 20s?
   I honestly don’t know how teens and even early twenty-somethings start businesses. Looking back at the beginning of my career, I was so naive. And I’m still learning. Through my career in technology, I’ve not only been able to learn valuable hard skills, but more importantly soft skills like how to navigate office politics, build relationships, manage a team, and understand broader industry-wide and consumer-wide trends and strategies. Beyond skillset, GNI also speaks deeply to me on a personal level as a later twenty-something. The fact that I’d rather stay in rather than go out means that I’m (hopefully) able to build the brand and company from an authentic perspective. It certainly helps that I’m able to empathize with our end-user and put myself in her shoes.
4. Did you aspire to be an entrepreneur before GNI or did you just happen upon a great idea and decide it was worth the risk of leaving a salaried job?
   I’ve always wanted and known I would start my own thing someday. I didn’t grow up in a family of entrepreneurs, but I think working in technology and seeing the many problems technology could solve was interesting and motivating for me. With Girls’ Night In, there is also the added layer of being mission- and purpose-driven. Our mission is to help women recharge and cultivate more meaningful community. I believe in our mission now more than ever before. I see the positive social impact it can have. That is what keeps me going.
5. What is the biggest mistake you’ve made with GNI and how did you learn from it?
   Our readers are so great because they kindly but passionately let us know when we mess up. I’m learning that editorial is a huge responsibility, particularly when you have such a large and fast-growing platform. I don’t come from a hard journalism background, so I’m learning how to manage this or hire stellar people around me to manage this. (Also, hi, if you’re reading and have experience managing editorial, email me!)
6. What has been your biggest accomplishment in the past year?
   Growing our audience to a combined 100,000+ members with no marketing budget, and growing the team to 12+ really talented members. This Vogue mention was pretty cool too, along with lots of other great organic press!

Support network: Me (second from left) at the Bustle Upstart Awards, meeting other rad women entrepreneurs.

BIZ ADVICE

1. I have a ton of business ideas but then always think “oh no, not another email newsletter” or “not another website that caters to helping women.” How did you get past thinking that another newsletter might not work because the market is already saturated?
   I think it’s important to have a clear mission, a unique point of view on how to achieve that mission, and something you’ve made that people want to pay for. Obviously, understanding the competitive landscape is important. But branding and building a committed audience is all about nuance. Within the same space, one newsletter or brand might work for one particular type of woman, while another might work better. The differences in reasoning may be really small, but they ultimately add up to build a brand preference in the consumer’s mind, and ultimately a competitive advantage for the business.
2. Literally how do you make money? Just sponsorships?
   Brand partnerships, events, affiliate link revenue. We used to sell products we designed in our shop.
3. When you first started out with GNI, how did you manage to work on your job and still have time, energy and motivation to run GNI? I feel pretty tired after a full day of working and all I want to do on weekends is recharge for the week ahead — so even though I really want to grow my blog, sometimes I lack motivation to actually do it, and then I feel pretty guilty about not doing it.
   It was difficult. If I were in your shoes, I would set up mini-goals and get crystal clear on the long-term goal for your blog. Do you want to grow it so that you can make X amount of dollars per month? Do you want to grow it so that you can flex your writing skills and use that as a data point on your resume? Do you want to grow it so that you can eventually quit your job? When that longer-term goal is clear, you can break this up into mini-goals, so that even if it’s 30 minutes to 1 hour on the weekend, you know that you are chipping away at it slowly. Feeling like you’re making progress is key to feeling fulfilled. It will take more time because you have a full-time job, but you’ll get there!
4. How did you approach funding? Did you have $$ saved up? Did you ask for investments or loans?
   We had no outside funding or investment. Yes, I had savings.
5. How did you keep up momentum and creativity starting GNI alone? I’m finding it hard to make my goals without the interaction from other people.
   My tips are: set up coffee meetings with people (for fun or for work), hire an intern and co-work with her/him, work out of a coffee shop, join a co-working space, and/or find a support group or even just one other founder who is in the same business stage as you are. You’ll learn so much from one another and be able to confide in and empathize with similar growing pains and challenges.
6. Is there anything you want people to know about taking a side-hustle to a full-time job that you haven’t talked about yet?
   I’ve had to exercise a ton of grit, perseverance and determination in the past year. In the earliest stages of a business, there are a ton of very high highs and very low lows. You have to have the mental and emotional strength to forge through. Making the leap sounds glamorous, but I’d caution you to think deeply about how it will affect you mentally, emotionally, and physically. If you’re truly passionate about your purpose though, I believe you’ll be able to pull through.

PRODUCTIVITY & SELF-CARE

1. What are some of the tools that you use to stay organized? (Slack, GCal, Asana, Evernote, etc.)
   My #1 tool is actually the dot-grid GNI journal (it’s sold out and now only available to our GNInsiders ambassadors, sorry!). I get SO distracted by technology, social media, and notifications. I love having one physical place to go where I can jot things down, get a little messy, and satisfyingly cross items out. For communication, our team loves Slack. For project management, we do a lot of Google Docs, Trello, and Asana.
2. Hi! Thank you so much for being open and allowing us to ask you questions. I love it. My question to you is how you were able to balance friendships and your health with a want to build a new career for yourself.
   Great question. I’ve found that now that my friends are nearing our 30’s, we’re all just a little bit busier and we have to actively manage time spent together. I have a couple of different friend groups that I group text with and we try to see each other regularly through that. I have long distance best friends as well, and we’re trying to make an annual trip a thing.
   As for health, this is huge for me. I’ve found that on weeks when I don’t exercise, I feel terrible, and sadly it’s so easy to fall into this trap when you’re running your own business. I’ve slipped up a couple of times, but for the most part I try to prioritize getting in a run. A perk of working for yourself means that you have the flexibility in your schedule to be able to squeeze in things like a run at 3pm when the last thing you want to do is be sitting at your desk. :)
   I think at the end of the day, we are all very busy, but we make time for things that we want to make time for. It depends on what you’re prioritizing at the moment.
3. What tools do you use to keep track of finances for the business side of GNI?
   Quickbooks.
4. What’s your daily work schedule like?
   I fiercely protect my Thursdays and Fridays and try not to schedule any meetings on those days. I need a full working day on Thursdays to get the newsletter together and handle anything last-minute that comes up. And I need Fridays to recover from the intense sprint that usually happens between Tuesday to Thursday! I also have learned that I dislike having meetings on Mondays — I like to ease into the workweek. As an introvert, knowing myself in this way is so important. What keeps me energized and what drains me, and how to balance all of that. I therefore stack most meetings on Tuesdays and Wednesdays. On that note, I tend to do intense “focused” work on Mondays and Thursdays. “Focused” meaning work that takes up a ton of brain power — i.e. less passive tasks, like copy-editing a piece — and more tasks that feel like really large, challenging, blue-sky tasks, like developing a thorough onboarding guide for new team members, or thinking through long-term strategy.
5. How do you take time for yourself, away from work? I feel like running a business would make it harder to destress and stop thinking about work, and I’m curious as to how you relax and take care of yourself.
   My favorite topic! :) I like to go for a run when I need a break. I’m also really big on skincare and iterating on my skincare routine and will make sure I have a couple of nights when I can spend about 15–20 minutes on skincare. “No screen time” is important too; I love picking up a book (hi, book club) and letting my brain cool off that way. Also, not gonna lie, I do love Instagram and think it can be very inspiring. However, I try to limit myself to about 10 minute bursts of “Instagram breaks” throughout the day.

Scenes from a recent GNI book club meetup in Brooklyn

COMMUNITY & THE FUTURE

1. How do you foster community in a positive way?
   I love this question and it’s something we think about a lot. First and foremost, I think it’s important to be clear on your mission, purpose, and values. Next, empower people within your community who are great role models in terms of behavior, participation, and leadership. We’re very lucky to have an amazing group of book club hosts across 9 cities at GNI who live out our mission and are great leaders. Lastly, set up clear guidelines and boundaries on how your community members should interact with one another that reflect back on your core values. Be ready to act on these guidelines and boundaries, even if it means disciplining or excluding bad actors. Building community is in constant iteration for us. If you have any feedback on this and your experience so far, please email us!
2. Will there ever be a podcast?
   We don’t have one planned for the immediate future, but it’s on the wishlist. ;)
3. What’s your hope for GNI?
   We have an important mission of helping women recharge and cultivate meaningful community. My hope is that we continue to grow, learn from and empower our community members, and help them connect with one another.

Photo by Heather Sten for GNI.

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