Free Coaching re-cap: side hustles, balancing your life, hiring, sales-on-site & outsourcing.


Hi Friends!

If you missed our monthly free coaching / consulting call, no worries! I've written a re-cap! You can join monthly by browsing our home page– we've always got a link for it up! 

Here's what you missed:

Q. When do you know it's time to hire someone for branding / marketing help?


My follow up questions to this were, "Is your marketing doing it's job? Is it working well for your business? Is it good? Or could it be better?" and then "When you think about doing the marketing for your company, do you want to die?" His answers were that it could be better and that he really did feel like dying when he thought about doing the marketing work. So, my advice was that NOW is the time to hire someone. His business is suffering from a lack of good marketing. And he doesn't want to do it. 

Q. What do you do to increase sales on site when customers are coming in to your booth and complimenting you but many are leaving and not returning to buy the items they were interested in? (this question was posed by a Vintage Vendor, FYI)

A. This is a complex question, and I would have liked to have a discussion with Britney but we weren't able to make technology work for us so I had to get some clues via just text chatting and piece together what's going on. However, I have some thoughts about on-site-sales and here they are:

  • How full is your booth? Shoppers loved packed vintage booths. 
  • How branded is your booth? Shoppers love looking at a vintage booth in 2 ways: as a super bargain basement treasure hunt OR as a storefront where the purveyor has a specific style that is apparent and on-trend.
  • Do you know your 4 dream customers? Do you know who LOVES your business and why? Knowing that about your customers allows you to do more for them like create vignettes, helpful blog posts, sales and take chances on new merch that speaks directly to them. 
  • Are you capturing everyone's email address? You should be building up your mailing list so that not all the pressure is on sales on the day of an event. Lots of people like thinking about vintage and then buying later.
  • Make sure your pricing / setup does't make you a commodity. What's a commodity? A commodity is an item that is now only chosen by price alone, because it's so similar to lots of other people. The opposite of a commodity is a brand that people LOVE and they buy because of that, regardless of price. Sometimes, oddly enough, raising your prices (if your quality is great) is enough to take you from commodity to a brand people love.
  • How are you at selling in person? Lots of vendors just sit in their booths looking miserable and no one really wants to have a personal interaction with someone like that. 

Q. When is the right time to tell your boss that you're starting a Side Hustle?

A. Interesting question. Would it be weird for your boss to find out from someone else or by stumbling across your website? If so, then you need to tell them up front. This person was worried that if they told their boss and then the side hustle failed, that maybe they were risking their job too much. BUT you should never make decisions because of fear. Never.  My tips for telling your boss about your Side Hustle:

  • Did you sign a non-compete? If what you're doing in your side hustle is similar to what you do at your job, your employer might not allow it. Even if you didn't sign a non-compete, it might make you less of a perfect fit for your employer since there's a big chance you'd like your side hustle and leave them in a bad spot.
  • Create a set of rules for your boss about how you'll ensure that your side hustle doesn't infringe on your current work. You need to be able to assure your boss that nothing will suffer at work because of your side hustle.
    • for example, when you're on the clock, you'll never be working on side hustle stuff. 
  • Create a 6-month plan for yourself and your boss. What ideally do you want your side hustle to do for your life? Do you imagine it becoming a full-time biz? What will you do if it does start to make your life super busy? It's good to know what you plan to do before you're thrown into a way-too-busy situation and have to quit unexpectedly or just slack on your full-time responsibilities. 

Q. Before starting your biz, i assume you were working for someone else, while trying to get your own thing up & running. How did you balance all of your other roles too without feeling overwhelmed & giving up 'me' time? (as a gf, employee, friend, mom, etc.)

A. It was a hard balance, honestly. And I was all over the place about what I wanted to do, and the recession made my life a little easier because my job disappeared! But here's how I did it:

  • I worked all the time. 
  • I was constantly reading and trying to find inspiration about what kind of business to start.
  • I settled on graphic design & wedding invites because a lot of my friends were getting married. 
  • I was really bad at a lot of things. 
  • I worked late nights and early mornings.
  • When a big client wanted to hire me on a monthly retainer, I decided to quit my job. It was scary!!!!
  • I lived on very little resources for about 2 years straight and I even moved into the Cleveland Hostel in exchange for branding + website building (so I got free rent).
  • Slowly, my side hustle became my main hustle and I found myself in the same situation with no 'me' time. So, I use a calendar to make sure I block off time just for stuff I love.
  • It's not easy at any stage of your life, so don't use that as an excuse to not have a side hustle or stay in 'super busy mode'. Be a BOSS and solve it. 

That's been this month's episode of Q & A with Steph! If you want to get in on next month's free coaching call, just make sure you're subscribed to our newsletter!




Stephanie Sheldon