Click here to read the post about how and why I started my blog. It answers a lot of questions that you might have as you read more about self employment!

When I first started dreaming of doing my own thing, I had so many questions. Unfortunately, I couldn’t find a lot of realistic advice or resources online. From what I remember, everything was all follow your dreams without much real talk. So many bloggers made it seem like they just woke up one day, quit their office jobs, and then the next day they were miraculously making 6 figures posting photos of smoothies. Umm, what?

Since my last Q + A post was such a hit (and because I like giving you guys content that you actually want to see) I decided to dedicate the second iteration to something I get asked about a lot: blogging + self employment. I remember feeling like nobody on the internet was telling the truth about the leap from corporate life to something less traditional. I hope that this post changes that.

Before we get started, read this post. It outlines how and why I started my blog, my previous work experience, and a bunch of other questions that you might have as you go through this.

I hope this answers your questions and, if you’re thinking about it, gives you the inspiration you need to start doing the damn thing!

What’s your best tip?

Without a doubt, make sure that you really, really love what you’re doing. It’s easy to glamorize self-employment, but at the end of the day work is work. There are going to be days where it drives you just as crazy as any other job. Make sure that you really love what you’re doing so that you don’t resent leaving a more traditional work situation (benefits, coworkers, having an office, etc!) behind.

Another thing that I don’t think people talk about enough - you absolutely can’t just be in this for yourself. if you want to take the solo route, it has to be about serving people, providing value where you see a need, and bringing value. I see a lot of people go into working for themselves wanting people to pay them just for, to put it bluntly, doing whatever the fuck they want. That’s not how this works. You have to be truly passionate about helping people, bringing them value, hearing their feedback, and serving them as much as possible. That’s probably going to mean that you pivot. A lot. That’s not a bad thing. Just know that to be truly profitable, truly successful, in working for yourself that you have to be willing to work for others.

I’m trying to figure out how to get endorsements for my blog as well as ads. There are no easy guides.

There are no easy guides for a lot of reasons, but mostly because each situation in blog-land is going to be really different and unique. There aren’t as many endorsements out there as there are things like sponsorships. A sponsored post is when you partner with a company and they pay you to write about a specific topic. I did this recently with Bartell Drugs. They gave me a topic to write about and a few things that I had to include, but outside of that they left it open. Usually that’s how it works - a company wants your unique voice to showcase their goods or services.

To be honest, ads aren’t a huge income driver for most bloggers. You absolutely can sell ad space, but I usually don’t recommend that bloggers go the way of getting ad servers placed on their site. Unless you have a HUGE following, it’s probably not going to be super fruitful for you. Instead, I would suggest reaching out to a company directly for ad space on your site, or offer that up to somebody that’s interested in working with you.

Something that I like to remind newbie bloggers is that companies, in general, aren’t just going to pay you. They want to work with you to showcase their products. I think that often the assumption with blogging is that we all make money talking about whatever we want and then money magically shows up. That’s not how it is. You will make money off of your blog or website if you run it as a business. That means making deals with businesses. You can absolutely do this with integrity and in a way that you really believe in - I work really hard to do this well every day. That being said, you aren’t just going to get paid for being on the internet. I wish!

The Influencer Podcast has a lot of great tips on rates, negotiating paid collaborations, and the like.

Health insurance! Is it doable to get on your own? It’s my one big issue because I have chronic health stuff.

I got this question from 10 different people!

I want to be fully transparent here - I’m married. My husband works in a traditional corporate setting and I’m on his health insurance right now, which I am VERY thankful for. So right now health insurance is incredibly stress-free for me. I know that’s not the advice that most of you want to hear, but it’s my situation.

That being said, it’s 100% doable to have your own health insurance. I’ve done it. It’s expensive. Especially if you have chronic health stuff (I do too!), but it’s a matter of prioritizing. I care a lot about wellness. Because of that, I spent more than the average person might on health-related expenses. It’s absolutely attainable - make sure that you do your research, plan ahead, and over-budget for your medical expenses. I think what trips people up in regards to buying their own health insurance is that they don’t make an appropriate budget that gives them wiggle room to enjoy life. Take time making a legit budget and you’ll be golden.

How do you segregate times for running your business? Set times? Weekends?

When I first left the corporate life I basked in the glory of not having a set schedule. That was fun for a few weeks, but then it started driving me crazy. Now for my own sanity (and so I have time to do the things I love), I keep pretty strict office hours. I set aside time on my calendar for certain tasks each day. I might book myself time in a coworking space or go hang out at a coffee shop. I use my journal to keep track of the tasks I need to do in order of importance and keep that list in front of me all day. Sometimes I will use project management softwares, too, but in general I like writing things down on paper. I keep very specific time slots available for certain things like meetings, private yoga lessons, or coffee dates. That helps keep me organized and also keeps my schedule predictable. I used to say YES!!! to anything, anytime. I ended up wasting a ton of time while also completely burning myself out - I was driving all over the city for meetings, had a lot of weird dead spots in my day, and wasn’t getting home until really late. I was exhausted, I never got to work out, I never saw my family, and I started hating my job. I learned from it and don’t operate like that anymore.

In regards to weekends, I keep them strictly off limit for work as much as I can since the rest of my time is pretty much fair game - some days I’ll start work coaching at 5 am and get home at 10:30 PM after a media event. A lot of my private yoga students ask for lessons say, in the middle of the day on a Saturday. That might be a great time for a student to practice (and such a treat!) but it keeps me from having any sort of full day off. It’s not uncommon for me to go about two months between days off, which isn’t something I want to do forever. During the rowing season (9 months out of the year) I coach every Saturday. A lot of our races are on Sundays. So for most months out of the year I’m already working on the weekends and have them set aside for rowing. I taught weekend yoga classes for years. At the time it was a great professional development opportunity, but now it’s just not something that serves me. Outside of rowing I try to keep any free time I have available on weekends for spending time with my family, catching up on sleep, and living my goddamn life.

How do you “advertise” yourself or sell yourself without sounding pushy?

I get this question a lot and, to me, it comes down to one simple rule -you have to have a genuine interest in what you’re doing. When you super believe in what you’re doing, you’ll never feel pushy. You will feel really excited to tell somebody else about what you’re doing, and making money from doing that will seem like this really cool added bonus.

I have felt pushy when I was selling TV ads or when I worked in menswear at Nordstrom in college. I felt pushy because I didn’t really care about TV ads or see the reason why somebody needed a $400 pair of dress pants. On the other hand, I believe deeply in yoga, mindfulness, CBD, and all of the other things that I write about on Donuts + Down Dog. I believe in them so fiercely because they’ve changed my life. When I write and/or post about those things, it’s coming from a place of enthusiasm. I’m excited to tell my readers about it. I’m fucking stoked to answer your questions. I am thrilled when a brand reaches out to me and I get to help tell their story. I feel so lucky.

If you are doing something that doesn’t fully align with your passions or goals, you’re going to feel pushy. You have to be comfortable backing up your business, advocating for the pay that you deserve, and educating people on why it’s important. That conversation can be uncomfortable sometimes, but it’s an important one to have if you ever want to get paid.

Also, read The Psychology of Selling. It’s a huge help in understanding the psychology of sales!

What things have you done online that ended up leveling up your business income?

Honestly, the thing that has helped me the most is that I have a background in marketing. I majored in Public Relations. I’ve worked for a major TV station. I’ve also managed social media for all sizes of businesses. That has been so incredibly helpful in scaling my business to where it is today - I can’t stress that enough. I meet a lot of people that want to start blogs who have backgrounds in careers like finance or event planning. That’s not a bad thing at all, but you’re going to be starting much more from “scratch” than I had to. If you want to launch a business, learn about marketing. If you have the income, hire somebody to do it for you. It’s so helpful.

Outside of that I spend a lot of hours dedicated to learning. I read business books, watch a lot of educational YouTube videos, and when my time/wallet allows for it I sign myself up for trainings. I try to stay ahead of the curve when it comes to learning new things that relate to my business. Each week I dedicate at least a few hours to learning - usually during my lunch/coffee breaks.

Do you have any self employment resources that helped you or still help you?

Yes! I was just talking about learning above, and these are some of my favorite resources.

Profit First - This is a great resource full of resources on setting up your financial structure.
The Psychology of Selling - Learn how to sell! Even if, especially if, anything sales-y makes you cringe. At the end of the day you won’t be able to run a business without making money, right? This book is a bit cheesy, but full of a lot of great psychology tips that have helped me reframe how I talk about my rates with prospective business partners.
The Influencer Podcast - You do NOT have to be an influencer/blogger for this podcast to benefit you! It’s full of tons of great marketing, social media, and general online business advice from a bunch of different experts across the board. The host does a fabulous job bringing guests of different skillsets on the show to share their tips.
How I Built This - My favorite podcast for business inspiration. I love hearing the stories about how big companies got their start.
Skillshare - One of my favorite resources for online trainings! Some are in-depth, some are only a few minutes. If there’s ever something I can’t figure out, this is usually where I go.
You Are a Badass at Making Money - Please read this, especially if you’re feeling down on yourself. It’s a little woo-woo and full of lots of mindfulness prompts, but it’s a huge help for reframing how to think about your worth and value.

How long did it take you to launch your business before you could quit your day job?

I blogged consistently for three years before I felt comfortable enough to leave my job at Amazon. That time running my blog while also being fully employed was absolutely vital. Running my blog while working a full time job forced me to sacrifice a lot of time - pretty much anytime that I wasn’t sleeping I was working on growing my business in one way or another. I spent those years delving into a lot of trial and error, online trainings, and networking with people who were a few years ahead of me. Having to make those sacrifices with my time forced me to confront the intentions behind my business, question if I really wanted to do this whole blog thing, and also gave me the flexibility to learn while I had a steady income. I also saved a lot during that time so that when I quit my job I was set up for success.

It’s really important that I share this piece because I know that it’s so tempting to just drop all of your responsibilities and chase your dreams. It might look like the people you admire are doing that, but trust that there was probably a lot of behind the scenes work going down that you weren’t aware of. I really suggest spending some time working on your business or “dream job” idea while you’re fully employed (maybe even at a job that you don’t like all that much) to figure out if this is something that you really want to do.

Do you have any suggestions on finding clients or customers when you first start out?

I heard on a business podcast once that you can’t just catch, you also have to go fishing. Essentially: you can wait for clients to come to you, or you can start getting out there and pitching yourself to clients. When you’re starting out, especially when you’re starting out, nobody is going to just show up and ask you to work with them. I constantly am DM-ing people that look interesting, introducing myself to business owners at networking events, and going to wellness events throughout the city. Start pitching! Look for businesses that are a little big bigger than yours and introduce yourself. Tell them about what you do, reference why you might be interested in working together, and see if they want to collaborate. Don’t immediately start with a sales pitch. It’s unprofessional, obnoxious, and not a great way to make business friends.

When you’re starting out, fellow small businesses will be more receptive to working with you because they are in the same shoes as you. I’ve seen so many brand new bloggers reach out to brands like lululemon on their first try and… that’s just not going to work. Those large businesses get contacted every day by hundreds of people who are hoping to collaborate or work with them. Start with somebody else who has maybe never collaborated with another business before. That way you can work through your kinks together, so that when that lululemon collaboration does come along you’re ready for it. Keep in mind that this might mean doing unpaid or low-pay work to start out. While I’m a huge advocate for getting paid what you’re worth, nobodies first job pays 6 figures. Put in your time. Learn how to collaborate. Start building up your work experience and things will only grow from there.

Obviously the paragraph above is pretty blogging specific but my advice for everybody is essentially the same: start introducing yourself to people. Go to networking events. Make connections. Build relationships. Set a goal for a number of meetings you want to have each week. No matter what your niche is, eventually business will start rolling in. Just remember - nobody will know who you are unless you tell them.

Q + A #2: Self Employment

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