The Side Hustle: How to run a business after hours


By Dannie L Fountain

As a part-time entrepreneur, there are many challenges that we encounter in terms of running a business, handling clients, and time management. We’re going to break those challenges down and go through manageable solutions line-by-line that you can implement in your business today!

Evening Hours

One of the biggest “struggles” we often inflict upon ourselves is the perception that working in a business during the evening hours is somehow less professional than during traditional hours. This simply isn’t the case. In the online world, it’s possible, even likely, that you’ll have clients that span time zones and continents. While your 4pm-10pm CST office hours may be less desirable for your clients in New York, they might be highly desirable for your clients in Australia (where it’s 9am) or Hawaii (where it’s 12pm).

Managing evening hours is less difficult than you’d think. Be upfront with your local clients and allow them to decide if your availability fits their schedule.  

Outlining your availability in your contract is a good idea. I have clients who know I work 4-9pm CST but will contact me during the day. Being protected by my contract allows me to give my day job the focus it requires without feeling obligated to respond to those messages immediately. Usually a simple and gentle reminder clears up any issues like this.

Time Management

When you have a day job, a side hustle, and a personal/social life time management can be difficult. There are three major tools that I use and recommend for balancing all three.

The first is a hard copy planner. I use the Start Planner but any simple planner will do. My planner has a three colour system (day job, side hustle, personal) that tracks appointments, engagements, and to-dos. At a glance, I’m able to see what I have on tap for all three based on the colours I see on today’s page.

The next tool is Google Calendar. I’m able to set up all client appointments in Google Calendar and it integrates with all the major online schedulers (Calendly, Acuity, etc.). It also updates automatically in my Mac iCal so I’m up to date on “current events” regardless of where I’m looking.

Finally, I use 17hats for project tracking. 17hats also integrates with Google Calendar and lets me note client meetings, deliverable dates, follow-ups, and any other major tasks. These updates then sync across all platforms.

To get a handle on the upcoming week, I spend about an hour on either Saturday or Sunday night double-checking that my planner is up to date.

As well as scheduling client meetings, I plan out what projects I’m going to work on and allot time to each one. This helps me stay on track and ensure that everything gets done. My VA and other team members work different office hours so this is also helpful for time management. If a client absolutely needs to meet outside of 4-9pm and I can’t make it, a member of my team steps in. We meet as a team on a weekly (or bi-weekly) basis to go over major deliverables on their end and to connect on any major successes or struggles.


Sometimes it can feel like you’re not a “real entrepreneur” because you still have one foot in the corporate world. The biggest thing to recognise is that almost everyone started where you are. Entrepreneurial businesses start as side projects and slowly evolve into a full-time responsibility. You may not yet run your business full-time, but you commit an equitable amount of time and energy to your business as those who do. Recognising your worth and not comparing “apples to oranges” will help you value how truly extraordinary you are.

These three major challenges that part-time entrepreneurs and side hustlers face may seem daunting, but when broken down line by line, they’re more manageable than previously thought! 


Dannie Lynn Fountain-Jagodzinski is the Founder of LE Consulting. Though she hails from Michigan and has been bitten by the travel bug, she now calls Chicago home. Through LE Consulting, she works with businesses and individuals providing marketing services. When she's not working with clients or experimenting with marketing techniques in the corporate world, she can be found reading a book, travelling the world, or enjoying downtime with her cat.