4 Questions To Ask Yourself When Building A Business That Fits YOU

Hey friend! The Weekly Wine Downs have gone LIVE! Last Wednesday I went live on my Facebook page, and now you can watch that video on YouTube (or below). I'll summarize the points in the blog post below, in case you prefer to read!

Starting my own business wasn’t something I really thought about growing up or throughout college. In fact, the idea of being freelance seemed terrifying and I know of numerous occasions where I said, very determinedly, that the idea of being my own boss was a big fat NOPE.

Well, after doing this whole freelance-be-your-own-boss thing for over 2 years, I can say -- y’all it’s pretty great. Yes, it’s hard, and scary, and challenging - but it’s also got a loooot of perks. After year 1 in my business I started to gain an understanding that not all businesses are or need to be the same, and using your own personality and desires and needs to build a business that works for you was an option.

This isn’t what I’d consider an ‘all encompassing guide’ to building a business around your needs - but rather, a discussion or reflection on things that have come up for me over the years that have shaped and molded my business into what it is today (and will continue growing to be in the future).


Technically, according to my Myers Briggs I am extroverted - but I think I fall into literally the most introverted extrovert there is. In knowing that, a few things came up in shaping my business:

I didn’t want to be on the phone with new/potential clients all the time. That’s just a fact - it overwhelms me to have to put on that ‘meeting new people’ smile. I’m great with people I already have built a connection with, but the idea of new makes me break out in a nervous sweat, makes my hands all clammy, and makes doesn’t bode well for my business’ bottom line. In year 1 of TheCrownFox I was doing branding design and that entailed a lot of calls with potential clients - cue the gag the reflex. In shifting into a retainer model, I focused on more long-term commitments and have way less client turn over - which ultimately equals me getting to be in my quiet little space, working, with no worries of multiple new client calls in a week.

"Build a business that fits into your dream lifestyle." (tweet that!)

Based on posts I see in Facebook groups, and articles I’ve read through Pinterest, it seems the online business community is split pretty 50/50. There are plenty of people who are extroverted and great at that initial connection - and their business model reflects that. Maybe they do 1:1 coaching with weekly calls, or 4-hour intensives where they have a new client or two every week! And if you fall into that category - you know, you thrive on change and new, you love that first meeting that is full of questions and excitement, and you are good at small talk - then maybe building a business that encourages that is the right move. In fact, you might get lonely if you don’t have that. For me, I don’t need to leave the house or see another human for a day, and I’ll be fine just working away with some candles lit and soft music on - so I adjusted my business to encourage that.


Right around the time I started my business online courses BLEW up. So, naturally, I thought I had to go that route too. And I did actually try for about 2 months to make that a thing! But within that span of time I realized that I am not a one:many (at least not yet, or maybe ever, who knows).

In reflecting on that, I realize that I would struggle to teach in a one:many capacity, because I would find it overwhelming as both the teacher and the potential student (I don’t do well with one:many courses, either). Being more of an introvert doesn’t mean that I hate people or anything dramatic, for me it just means that I need quiet time and space to grow and learn and refuel. That same mentality applies to courses, teaching, etc. I need time and space to foster connections with people, and I need one:one or one:few to not feel overwhelmed by the magnitude of anything and just stop dead in my tracks.

If you’ve taken a large course and felt it helped you, you might fall into a category of someone who is more fit for the one:many approach. In thinking of your own business, and potentially scaling it, maybe courses and those sorts of programs are an option because you can have a large number of people depending on and looking to you for answers. I, on the other hand, have to approach it as me and this one other person, or maybe 4-5 other people, are working together to better their business or lives. That’s the most I can handle, and as soon as I realized that I walked away from trying to create an epic course immediately.

In the future, I do see scaling through programs and not directly ‘design-for-hourly’ (like now). But, in knowing my personality and limitations, I think that it will be capped at a small number of people so I can best serve them and vice versa. This question for you truly may take time and reflection, if not trial and error, to figure out how you best operate.


This is another question that I have asked and reflected on, and probably the one that has given me the most difficulty in my own business. A lot of us get into this entrepreneurial world for time freedom - but then fall into regular expectations of working 9ish-5ish, especially when we have clients and meetings that require those hours.

My first few months of business I was maintaining my ‘but I’m a creative!’ rebellious attitude and adamantly rejected ‘normal hours’. I worked from 10pm-2am, slept until noon, etc. This did NOT bode well for my business… because despite the fact that we want and crave this ‘freedom’, things still essentially operate on a normal schedule.

I’ve since adjusted and keep pretty regular hours (I even try very hard NOT to work on weekends). It’s been a fine transition for me, I need some structure in my life, but I do reflect on one day being someone who travels more and wonder how to adjust my ‘hours’ to fit that.

The good thing about how I work now is with the exception of a few meetings, I can keep pretty irregular hours. So, if something does come up in the middle of the day that I need to do or take care of, it’s not the end of the world. When I switched into this retainer type model that was something I really relished in - because time freedom is at the top of my priorities.

For you, when it comes to shaping your business, take time to reflect on how you best work and what your real desires are, and if a more rigid schedule is a good thing for you, etc. My advice, based on my own experiences, is to try and maintain some sort of hourly structure (even if it’s not ‘normal 9-5’), so that you can tell people when to contact you, etc. If you want a business with no actual hourly expectations, you might need to look into a product based business or something that doesn’t involve team meetings, client calls, etc.


Something else to consider is whether or not you want a small number of BIG clients or a lot of smaller clients (or one really expensive product, or multiple smaller products). Both have their pros and cons. Having a few number of BIG clients means less ‘switching gears’ in the middle of your day, less ‘oh shit panic’ from the clients (well, just less clients to have last minute requests all at once), and more comfortableness on the team. However, if you lose one of those clients, that could be huge to your finances. Having a lot of smaller clients means that if someone doesn’t pay an invoice you’re not scrambling, because there are plenty of other invoices coming in…

For the first year of doing retainer work I was in the ‘a lot of smaller clients’ realm. That felt safer to me, plus I hate saying no to people. Lately though, there has been a shift in the caliber of client I attract (thanks to raising my prices, gaining more experience, and better showing off my sample work), and that has resulted in having a few BIG clients. Right now I am sort of right in between but shifting towards a few BIG clients - which is both scary and exciting, but I realized, moving back to my first point, that I work better with less on my plate and with really fostering a small number of relationships.

Deciding which approach is right for you, here, might take experience in both sides to see where you feel most comfortable. Though, I can say, if you are someone that can handle hustle-bustle and not get overwhelmed (unlike me), having a lot of clients probably won’t phase you.

Those are some of the main questions and sort of bumps in the road I’ve hit over the past two years in shaping a business for myself. Where I’m at now leaves me plenty of time for reflection and self-care, let’s me only need to ‘get presentable’ 2-3x a week, and has me feeling confident in the money coming in each month to cover my expenses and pay myself. That’s not to say there aren’t plenty of other factors that come into play, and that we aren’t constantly evolving. In fact, for 2018, I see my business evolving even more as I plan to introduce more products, templates, and workbooks into my shop - but those developments all come from reflecting on the above questions.

Some other questions that have helped in shaping my business now, and will have an effect on the future of my business include: “how can I run a business if/where internet is spotty/not always available” (I want to travel more), “how can I create more autonomy without losing personalization and communication?” (This is important to me, I never want to be sterile sounding), “if I sell products, does working to convert a few BIG sales seem harder or easier than many SMALL sales?” (I’m leaning towards smaller products). Just some things to think about…!

How have you built a business that best suits you?

I’m Kaitlyn, your design assistant! I work with successful creative entrepreneurs to create cohesive, clean, and compelling visuals for their businesses. You can keep being the #girlboss you are (but with more time to focus on growing your empire)! Let's set up a time to chat!