Pros and Cons of Starting a Side Business

I’ve talked a lot about why starting a side business is one of the most declarative, legacy building, career changing things you can do for yourself. (Like here and here).

It will hone your professional skills and add grit to your bones.

It will also open you up to new possibilities you never knew existed and light you up from the inside giving you that extra entrepreneurs’ I’m-doing-it-my-way glow. 

That’s the power of being your own boss and purposefully creating something that you put into the world.

That said, it’s not all sunny sparkles and mid-day-I’m-fabulous-cappuccinos.

There are very real challenges to juggling a full time day job with a side business. Boredom. Exhaustion. Frustration.

And yet, it’s all worth it. Really.

Below, four women share the pros and cons of having a side business while working full time elsewhere. Not only did they do it – proving that it’s possible! – but they’ve gone on to grow their businesses into full time gigs and happy bank accounts.

Natalia, at Website Superhero

I'm Website Superhero, caped provider of web design/development & strategy for world-changers. My mission is to help women entrepreneurs and activists make a bolder impact and more money with websites that are professional + beautiful + powerful.

But I wasn't always Website Superhero... I started out as a literature and gender studies student-turned-copywriter and copyeditor. Eventually, that ceased to challenge me and I stumbled upon web development and related disciplines. BAM. I was hooked. So here I am! Still a nerd and feminist and now a geek as well.


  • TONS of things to learn when starting a side gig. Which was excellent because part of the problem with my then-job was boredom, since it didn't challenge me. So I was having fun and excitement with my new venture! Mental stimulation for the win.
  • Psst... more work means extra money!
  • Meeting new people and helping new people. SUPER cool.


  •  More work means less leisure time
  • Did I say "more work" yet?
  • Working on weekends and all the time when starting out to turn it into a full-fledged biz. But honestly? If you enjoy the work, it's not so bad. It does remain super important to work out and sleep enough and eat well, though, or you're gonna burn out.


Halley, at Evolve and Succeed

Hi, I'm Halley Gray and I work with small businesses to get them booked out with clients or busting with sales thru marketing experiments + strategies.


  • Made my dreaded day job easier
  • Helped me fund my business + hire experts
  • Gave me a feeling of purpose that was missing before


  • Less time with loved ones (who actually didn't mind, they just worked on their own projects
  • Lots of new + exciting work that made my day job even more boring in comparison
  • A lot of uncertainty (but even more excitement)

    (Although it was tricky it was really, really worth it especially looking back now as a full-time business owner who has had their first 13k month, and been booked out for the past 6 months.

Deb Cooperman, at Deb

To bring home the (turkey) bacon (and other life sustaining products) I’ve been an entertainment writer, professional theater publicist, a teacher, marketing manager at an Inc. 500 company, and the promotions director at The Coaches Training Institute. Through it all, I was journaling as I had been since 5th grade.

About 10 years ago I started imagining how I might be able to combine my experience as a writer and journaler with life-coaching, and so began the dream of solopreneurship.

I started holding monthly writing workshops while I dreamed of leading creative retreats; in-person and on-line workshops, e-courses, and preaching the journaling gospel. About 3 ago, I realized that if I didn’t take it seriously, the dream would remain just that. I started enrolling in classes, joining on-line communities for creative entrepreneurs, and plotting, planning and visioning — and having less veg-out time on the weekends.

I gave notice at my job in February of 2014, and had my first solopreneur day on June 16.

It’s not easy, but I don’t regret it for a second. I love setting my own agenda and goals, and helping women experience the transformative power of writing. Not too shabby.


  • THE STRUCTURE. When there’s not a lot of time, you have to be super-effective about how you use it. While I was in my day-job, I became really selective about my offerings (only one), and how I would promote the side-hustle work. My goal was to just get really good at what I did, create a loyal following (even if it was small), and build a solid plan and back-end infrastructure.

And that leads into the second thing I loved …

  • THE MONEY. I loved having a steady paycheck … and someone else paying for my health insurance … and holidays! It was freeing to know that money was always coming in no matter how my monthly workshops went. It helped me focus on goals that were not about the bottom line when it came to building my biz.


  • THE TIME CRUNCH. While I liked the structure the day-job provided, my side-hustle often got the short shrift. I had a demanding job and I’d often come home pretty drained, craving restorative time, so it could get pretty exhausting. Luckily, what I know about journaling and writing practice came in handy: sometimes just 15 - 20 minutes of free-writing would give me back the energy the day had drained, and I could focus on the side-hustle. But also, thinking of the side-hustle as a practice was helpful too. Instead of having to fly right away, I created it bit-by-bit; day-by-day.


Shauna, at Up and Running

I'm Shauna Reid and I'm co-founder and community manager at Up & Running, where alongside my running coach pal Julia Jones we provide awesome e-courses and training plans for women, from walking to 5K to marathon.

When we started in late 2010 I had a full time job in digital marketing for a travel company. 

After a great first year in business, I crunched the numbers then negotiated a reduction in day job hours to 3 days/week. I did that for two years before going full time in 2014.

I was a zombie that first year - starting the business coincided with a day job promotion. There were days where it felt like I was just doing a lot of things, poorly. But I got better at prioritizing, compartmentalising and focusing like a freaking laser. I got up earlier, made use of lunch breaks and worked weekends. I learned to calm down the anxiety and reduce my procrastifaffing.

It was a very anti-social year. But with financial obligations, chucking in the day job right away was not an option. I'm a cautious person at heart, so gradually easing into entrepreneurship worked for me.


  • Secure income and peace of mind while testing the viability of our business
  • Since my day job was applicable to our business, I pounced on any opportunity for training and networking
  • My sharper focus benefited both Up & Running and my employer!
  • Switching to part time hours gave a great balance between Working In My Jammies and Real World Interaction!


  •  Fatigue
  • Self-doubt exacerbated by fatigue!