These days, I mostly hang out at Workweek Lunch, writing about meal prep, cooking and intuitive eating. My Instagram audience knows I won’t dive deep into entrepreneurship in a space where I prefer to keep it focused on meal prep, but the other day I encouraged questions about entrepreneurship.
In this post, I’m going to answer some common questions I get asked about building a business, making the leap from employed to self-employed and what I’ve learned along the way.
How does health insurance work as an entrepreneur?
Lucky for me, I was covered by my mom’s health insurance until I turned 26. (I’m still 26 at the time of writing this blog post!). So I’ve only had my own health insurance for a few months now.
I spent a good amount of time researching the best options for me in terms of price and what I need (which is very basic, as I’m fortunately pretty healthy) and landed on Oscar for my main insurance. So far it’s decent!
Actually signing up for health insurance was so much easier than I thought it would be. It took a few phone calls (I’m old school like that) and within an hour, I was completely set up with vision, dental and medical health insurance. It only sets me back a few hundred dollars a month, but it’s worth it.
How exactly did you know what to do? I am thinking of starting a side gig and have no idea where to start.
At the beginning of my side hustle journey (which I started when I still had a full-time job), I remmeber listening to a ton of podcasts and reading loads of blogs about side hustling.
I got a strong sense of what kinds of side hustles you could do. Dog walking, being a personal assistant, tutoring, selling products on Etsy, flipping items on eBay, taking headshots, selling clothes and driving for Lyft or Uber are all great examples of side hustling.
I landed on ghostwriting and freelance writing because I was a writer by trade. Of course, I kept this on the down low, because earning money on the side was a writer while having a full-time writing job was a little risky. But I never got caught.
My best advice is to start researching side hustle ideas and go down an Internet rabbit hole to learn exactly how to execute that side hustle. Chances are, someone has already done it (and talked about it online).
You can also turn pretty much any skill into a side hustle.
Are you good with a camera? Offer freelance photography.
Graphic designer wiz? Get started designing logos.
Do you love embroidery? I bet your stuff would sell well on Etsy.
Teaching yourself how to code? You can pick up freelance jobs on Upwork and pretty much get paid to learn and develop your skills.
The options are endless!
Scared of failing? You have MORE to lose by NOT trying this out. It’s just a side hustle!
How do you battle the mindset of fear with money and being afraid to not make ends meet?
It’s not an easy battle. I fought this battle in 2017 and half of 2018, but I made it through.
But here’s the truth. If my business burns and dies for any reason, my back up plan is simple: get a job.
Landing a full-time job is not hard if you have to get back on your feet after an entrepreneurship failure, and need a steady paycheck for a while. There is NO SHAME in that. Not all business endeavors work out and some part of you has to accept that going into it.
So that’s how I got over the fear part. And in 2018, I considered getting a regular full-time job twice (and even interviewed for jobs!!) when it seemed like I wouldn’t be able to make ends meet. But the universe kept bringing me back to entrepreneurship. My life is funny that way (and maybe you can relate) but every time I was about to jump ship, money just kind of showed up when I needed it most, and I was back on track.
What if you can’t make ends meet though?
Another reality of entrepreneurship no one talks about: credit card debt! I got into some credit card debt in 2018 in order to keep going because I didn’t have any savings then. It wasn’t fun, and I did get out of it, but it was necessary.
The more I talked about my debt issue to fellow entrepreneurs, the more I realized how common it is! Knowing that credit card debt is normal when you’re bootstrapping a business made me feel more confident and less like a failure.
I’m not saying you should go into debt and everything will be fine. I can’t promise that. So don’t take that story the wrong way!
How do you stay on track with tasks that build your biz?
I love this question!
There are a few systems I have that help me continue to work on tasks that grow my business. Trust me, it was a learning process but I’m closer to nailing it than ever.
- My mentor. My mom is my mentor (she’s mentored dozens of entrepreneurs in her career, and is a successful entrepreneur herself). We meet a few times a month for a few hours at a time and get down to business. We look very closely at all the numbers and determine what’s working, what’s not and what I need to focus on. Mentorship is crucial.
- Setting yearly and quarterly goals. This can be done with the help of a mentor, or not. For the last few years, I’ve planned out quarterly goals that support a yearly goal. I split each quarterly goal into very granular bite-sized tasks to get them done. If you put “Get 5 sponsors” on your to-do list, you’ll never do it. But if you put “Find XYZ company’s contact for sponsorship” that’s a lot easier to get done, then move to the next step. I write all of this out in a google doc that I look at every Sunday.
- Every Sunday, after I look at my quarterly goals, I then create specific tasks on my calendar. I carve out time for what I have to get done to keep my biz running and what I need to get done to keep my biz GROWING. It’s a hard balance to strike and it takes practice! If it’s not on your calendar, it doesn’t exist.
It’s not always perfect and I had learn what impacts my business an what doesn’t. My goals are rarely fully met because I set them high and slightly out of reach. But this is how I get it done. Have a plan, then have a plan to execute it!
How did you learn about how to build a website? I feel so lost.
This is one of those struggles no one told me about, and it only gets more complicated and more expensive as a business grows. Yay!
Workweek Lunch is built on a WordPress site. I use WP Engine to host it (it cost $30/month when I started, now it’s over $130/month) and I used Hover to purchase my domain (just $12).
WordPress is awesome because it’s made for people like me who don’t know how to code, but once your platform/product/business becomes more sophisticated, it’s tough to keep using. That’s kind of where I’m at right now.
But I highly recommend it for anyone starting out because it’s easy to set up and use, it’s affordable and their support is AMAZING.
Now, as Workweek Lunch becomes more advanced (and more profitable) I’ve actually hired a WordPress designer and developer to give Workweek Lunch a new look.
The main takeaway: you do not need a fancy, sophisticated website to have a successful content-based business. My site looks like total shit, but it’s home to a thriving 6-figure business and I haven’t really changed it in 3 years! In the beginning, the website just needs to function.
How do you maximize social media marketing and translate it to revenue?
I wish I had a sexier answer for this.
I maximize social media marketing by communicating my brand values and what I have to offer. Social media both attracts potential customers/gets them familiar with my brand AND acts as a sales channel.
Right now, obviously Instagram is my biggest social media marketing channel. I have 270,000 followers and nearly 20k daily story viewers at this point. But I’m working on expanding my community to Facebook, YouTube and Pinterest as well. Recently, I’ve started using Facebook and IG ads too.
In terms of translating it to revenue, the ebbs and flows are pretty obvious: I earn more as my following grows, when I’m more active on social media and as I continue to build trust with my audience on all channels. A big piece of this is actually selling on social media too (teaching people about my offer and using strong copywriting to persuade them to purchase) which I know some people are scared to do. If you have an amazing, real offer that actually helps people, there’s nothing to fear.
Related: How A Big Instagram Account Makes You Money
How did you know when to make the jump from employment to self-employment?
I didn’t! I got let go from my job in 2015 and that was the push I needed to give self-employment a shot.
After I got let go, I gave myself three months to figure out self-employment. I decided that if I couldn’t generate a certain amount of money per month on my own after three months, I’d get a job. But that day never came, and I never had to get a job. But don’t forget that I came close a few times, as I mentioned earlier!
My best advice is to start before you’re ready. Don’t wait to feel ready.
The only thing you SHOULD have in place is savings and a backup plan like I did. If it doesn’t work out, oh well. And if it does work out- great! You can always just get a job if it fails.
What resources were valuable to you when you were starting out?
As I mentioned earlier, I read a lot of blogs and listened to podcasts to learn about online business, entrepreneurship and side hustling. I read some books too, but I’d be lying if I told you I’m an avid book reader.
Once I knew I wanted to dive headfirst into building an online business, I joined a course called Zero To Launch. It was really expensive ($2,000, but I paid monthly for a year) and scary to join, but that course is the reason Workweek Lunch exists. ZTL gave me a strong foundation of tools and skills to build my business on and the investment totally paid off.
Could I have built this thing on my own? Maybe, and it would have taken me a lot longer. I have no regrets about investing in my education!
Another resource was my community. I made friends with other entrepreneurs, went to entrepreneur events and attended free meetups in NYC.
What are your best productivity hacks?
I think the best way to become productive is less about hacks and more about routines and systems, but everyone has hacks they love.
- Use the Pomodoro Method. This involves setting a 20-minute timer to get a task done. It helps you focus on that one task because you know you’re being timed! I use this for dishwashing, answering annoying emails and other tedious tasks that are easy and important, but not urgent (those are the ones we usually put off).
- Go with your flow. If you’re in a position like me where you’re in full control of your schedule, don’t try to turn yourself into a morning person if you’re not naturally one. Go with your energy flow to maximize productivity AND give in to the periods of the day where you really don’t feel lke doing anything. This helped my productivity a lot. I catch it like a wave when it comes, and don’t force it when it’s just not happening
- Outsourcing. If you can get someone else to do things you don’t really want to do, that’s golden. I now have 8 part-time people helping me with all kinds of things, from editing YouTube videos to managing customer service emails. Almost everything I outsource I can do myself, but I choose to delegate instead!
- The reward system. Tell yourself “I can’t do X until I’ve done Y.” This works for me when there’s a show I really want to watch, but I also have a lot of emails that need my attention and it works well!
- Take shit off your to-do list. Some stuff just isn’t important and you have full permission to NOT do it. And just because you take it off your to-do list now doesn’t mean it can’t go back on later.
Phew! I can’t believe I just wrote over 2,000 words on this stuff. I hope you found something helpful in here, and if you have any follow-up questions you can always reach me at firstname.lastname@example.org.
What should I write about next? Tell me below.