A raw inside look: Career creative turned creative mamma

Freelancing is a word that makes me cringe. It’s associated with cheap labor, work on the side, finite hourly rates, a hobby for a little extra money, everything but a serious high-level professional career.

In my 13+ years of being in business for myself, I have assumed the role of entrepreneur, business owner, and consultant. I remember early on when another designer and business owner, a man, asked me how my freelancing was going. I strongly stated that my new business venture was off to a great start.

Especially for women, and even more so for mothers, we need to present at a rate of 200%, the forefront of our capability to move the needle, to generate profit and sought-after results for our clients. Positioning ourselves as highly valuable specialists is THE KEY in being compensated appropriately. As an Italian-American born and raised in the US, I had thought I was aware of the gender gap in business dealings and in pay, but it is nothing compared to the situation in Italy. Together as a highly capable 50% of our global society, we owe it to ourselves and our future generations to continue to rise up.

I began working on my own little by little and officially became an entrepreneur in 2008. Having worked on my own for such a long period of time, I’ve constantly learned, flexed, and changed.

These are some of my most important tips for working on your own:

1. Have a designated work space.

I’ve run my business from a beautiful full extra bedroom turned office, a shelf in a closet, and the corner of a kitchen table. No matter how big or small, that was the place I’d go to mentally enter work mode.

2. It’s okay to change where and how you work, and most likely it will change.

Many entrepreneurs experience the need to shift where they work—going through phases of several years in a home office to daily visits to a cafe to working from an actual brick and mortar office or co-working space. It’s important to be aware of your needs. As a mom of a young child, until the pandemic, I worked around the hours of preschool from my car, from cafes, from the school’s lobby—I maximize space and time wherever I can.

3. You determine your work schedule.

I have gone through multiple periods of anxiety and trauma that led me to do some really deep work in finding ways to be mentally healthy while running a business, being a mom, and being me–an adult citizen of the world. A business strategist and mom shared this tip with me: It’s okay to NOT work every day. If you’re experiencing anxiety or going through personal struggles, change your schedule. You are your own boss, and you have 100% authority to define your schedule.

I know a designer who makes every Wednesday her “creative health day” designated for self-enrichment and creative projects that indirectly support her business.

As you’re building your schedule, it’s helpful to recognize that different tasks take different types of energy, and this varies from person to person. For example, I love getting on sales calls, and I naturally enter a kind of manic state while doing so. I don’t automatically come down when I hang up the phone. I used to try to make calls between design production, building strategies, and research, but just shifting from one type of energy to the other was mentally exhausting.

Since I am an executive, I made the executive decision to not do both on the same day or in the same block of time.

Also, as a mom, there are certain tasks I can do while my daughter is home/ awake and some that require extreme focus. Recognize what these are and plan accordingly.

4. On and off

One of the hardest things about working at home is just that–always being at home. There is no explicit on and off. I create rituals for myself that help in creating this much-needed mental shift.

I get dressed in a way that makes me feel productive–comfortable clothes that elevate my mood and light makeup.

I know a web designer finishes work in her home office and spends 15 minutes lying down on her bed before going to cook dinner. For her, that transition is the key to feeling healthy.

5. You can work on your own but don’t let yourself be completely alone

Something that changed the way I work is connecting with other professionals in my field, in my case, other creatives. I started taking online workshops in 2010 way before they were the norm, and I’m still in touch with numerous people I met there. We support each other in so many ways.

Connect with other professionals by taking courses, joining Facebook groups, and attend events whether online or in person. Working from home can feel incredibly isolating. Having a network of professionals in my field and in other disciplines, as well as other moms who are business owners has been my lifeblood.

6. Shift your mindset around distractions

I generally list what I need to accomplish for the day choosing my top priority items and making my list intentionally short to set myself up for feeling accomplished—especially important as a busy mom. If I’m struggling to focus, I’ll use the pomodoro technique—set a timer for 30 minutes and illuminate all distractions—only work to accomplish the set task. Take breaks, go outside, stretch. Sure there are times when you need to push hard to meet a deadline, but that’s not everyday.

Something I hear a lot is, “Aren’t you distracted by messes/ things you want to do at home?” I don’t think about those things that way. I am 100% in charge of my time. After eating breakfast and getting myself ready for the day, I might put a load of laundry in the washing machine, grab a cup of coffee & a snack and get to work. Then before lunch, hang the laundry out to dry, eat while listening to a podcast or connecting with friends before getting back to work. The point is, all of these things are elements of my life, and they all need to get done.

A colleague of mine who’s a mom of 3 and runs a successful business talks about outsourcing for her business focusing first on things in her personal life—cooking & cleaning are outsourced prior to hiring an assistant. Although at first it sounded like a luxury, the more I thought about it, this makes total sense. Managing a team takes a lot of energy but removing things from your list of to dos like cooking and cleaning only makes you feel more accomplished and thus more mentally available for yourself, your family, and your work. In my case, cooking is creatively therapeutic while preschool/ childcare is my most vital outsourced item.

7. Set boundaries with clients

An incredibly common complaint of solo entrepreneurs is that they have clients texting them on the weekends and late at night. If you set boundaries, this will not be an issue.

You are a business. Establish business hours and protocols. If you respond in the middle of the night, you will be expected to continue to do so, and they will continue to cross this boundary. When I was living in Japan, all my clients were in the US and Europe. I let them know the hours I was available and used Calendly (a free scheduling tool that shows in the viewers time zone) to allow people to request calls during designated times.

I have NEVER given out my phone number and in 12+ years, that has never been an issue because that is the protocol and expectation I establish.

8. Real life happens, and you need to be ready for it.

When I became pregnant with my daughter, I never shared this news with any of my clients. I was convinced that I would be thought of as less capable and that my baby would be blamed for me not delivering on time. These were all beliefs I’d manifested on my own. I’ve worked through this and still struggle with having doing the dance (I don’t believe in balance) between being a parent and a professional, but I have systems in place that help. I allow more time in my schedule than I think I need, and I make sure to understand my clients’ true needs with deadlines to know what buffers are possible should I need to push out a deadline.

Taking time off is your right. I know a solo entrepreneur who closes from November-January every year. I know others who work 4 days a week. Define what is best for you, and remember that can change.

9. Always protect yourself.

When money is involved, things get strange when you least expect it. The best shift Ive made in my business is on my schedules for payments. Starting out, I would request 50% to start and 50% when I sent the final deliverables. The problem was, I constantly had clients delay for one reason or another which meant my cash flow was interrupted. I switched to have 2 options: 1-pay in full 2-calendar-based installments (50% to start, 25% after 21 days, 25% after 40 days) Surprisingly, most prefer to pay in full and be done with it.

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My story

My name is Jaime Di Dio. I’m an Italian-American of Sicilian origin born and raised in Los Angeles, California. I studied Interior Architectural Design at California State University Long Beach and spent one semester in Florence, Italy. After graduating in 2005, I immediately moved to Tokyo, Japan and began teaching English while taking on graphic design projects and studying with an established Japanese designer.

I moved back to California in 2008. Not able to get a job in interiors, I co-founded a graphic design studio. We had no clients, so I went to the local city hall, found out what upcoming events were on the calendar, and volunteered my services to brand the city’s environment day fair. Every business contact I have today can be traced back to that single event. I started with the tagline, “If you need it, we can do it,” and quickly evolved to become a specialist as a brand strategist and creative director for wellness and socially conscious businesses. (If you follow me on Instagram @jaimedidio , you’ll see that I’m a major proponent of specializing as a direct result of my own experience.)

I held the position of instructor at University of California San Diego and served on the board of directors of multiple community organizations in addition to fully producing and consulting on multiple city events.

When my daughter was born in 2016, I took no maternity leave. I was in the hospital being induced, sitting on a yoga ball, and writing emails. I do not recommend this and would not do it again.

We returned to Japan when my daughter was 3 months old. I continued to run my business working with clients in the US & EU during the hours of 3:30am-7:00am and during nap time. This led to a complete burn out, and I was unable to work for 3 months. We moved to Hawaii in 2018.

I continued with the same work schedule sometimes shifting to evening to accommodate my EU accounts. I burnt out two more times and finally got the support I had long been asking for through enrollment in preschool for my daughter. Acupuncture, reiki, meditation and working with a life and business architect have been monumental in recovering from burnout and navigating a path to the personal and professional life I desire.

I’m currently an independent parent living in Honolulu, Hawaii. I am raising my daughter trilingually—English, Italian, and Japanese. She also shows interest in Spanish and French. With family and friends on almost every continent, I consider her to be truly a citizen of the world. We are pausing on physical travel for the time being, but I have every intention of continuing to live in a multicultural atmosphere which will take us to our next location(s).

You can find me on Instagram @jaimedidio and on my website www.studioaiuto.com

This post is also available in: Italian