How I Made The Transition From My 9-5 to Full-Time Entrepreneurship


I am Jess! Ottawa brand strategist and website designer helping ambitious service-based businesses grow with confidence through meaningful design. I'm the type of gal that use one too many exclamation mark in my emails and can only have one cup of coffee a day. Weird, I know. If you ever want to chat any thing biz, branding, or well - life, feel free to reach out!










Let me preface this by saying that it took a lot of mindset shifts and “should I, should I not” conversations in order for me to make the transition from my 9-5 to full-time entrepreneurship. Way more than I will cover in this blog post today…

Did I always want to be an entrepreneur? Hell no! I didn’t grow up in a family of small business owners so I was never exposed to business life. My parents also didn’t immigrate to Canada with $20 in their pockets so we didn’t experience the kind of hardships other immigrant families experienced. I was fortunate that when my parents decided to move to Canada, they were both excelling in their careers and spoke decent-enough English to get by. But by the time we were older, we started to see the cracks in our family – mostly due to finances and the fear surrounding it.

That’s not to say they didn’t sacrifice for me and my brother, because truth is, they sacrificed their happiness and marriage together in order for us to succeed. Every decision they made was to ensure that we have a successful, stable career that took care of us so that we don’t ever have to experience hardships.

Which was why it made the decision to leave my “stable” 9-5 corporate job that much harder when push came to shove. A lot of internal, family pressure.

A little back-story…

Over the course of my mid-20s, I always had that voice at the back of my mind nudging at me to do something different in my career than the traditional yellow brick road that my parents carefully laid out for me. Something impactful or life-changing, I thought. Except I had no idea what that looked like. After all, I only knew of what my parents suggested: find a government job, keep your head down, do good work, and stay as long as you can.

Of course, by the time I was 25, I decided against it and launched my first business as a wedding planner. I remembered how bright-eyed, bushy-tailed I was. Eager at the opportunity of doing something different. A year in, I knew deep down that something was missing. Perhaps the impact piece that goes beyond “the big day”. I didn’t feel as passionate about it but yet my ego was telling me desperately not to quit and be viewed as a failure, especially to my parents who I desperately convinced this was the “right path” for me… and also people within my network. So, I put a smile on and kept at it… after all, it will get better, right?

Around the same time I was at crossroads, I came across the Bucketlist Bombshells that sparked my creativity and got me excited about the possibility of design. It was my first “big” investment outside of my rent (LOL) but it spoke to me in a way that I have never felt before. I decided to stick with it and months later… the pandemic hit.

Which, I guess in a sense, was a blessing in disguise because it was when I decided to close the doors of one business and open another. When I founded Studio Crescent (previously known as Grace & Oak) in 2020, it felt different this time. It could be maturity for all I know, but I also felt lighter. As if everything in the universe was aligned and that I was on the right path to something bigger. I was lucky that when the pandemic hit that I wasn’t furloughed at my 9-5. Instead, the organization grew by 30% in personnel! But what that meant for me was that I was able to invest a lot of my salary into professional development and education, which was something I avoided doing in my first business. Immediately, I saw a return on investment that propelled me forward in a way that I didn’t think was possible.

Some of the business resources I invested in early-on (<12 months) that were worth every penny:

(There are probably a handful more of courses but I found the ones above really helped move the needle!)

Some of the business subscriptions that I can’t live without and save me SO much time:

* paid products

Disclaimer: I totally understand that not everyone has the means to invest right away in various platforms or professional development, but I did wanted to share my experience. Having the opportunity to invest in all of these things before making the full leap also helped me planned ahead financially!

So, what steps did I take to ensure I was ready?

I have always had deep-rooted, unresolved insecurities around self-trust, so when it comes to big decisions like this, my mind spins just a bit out of control and am in need to all the validation. You can probably guess that this stemmed from my growing-up, or maybe it’s something that has built overtime with various relationships and incidents in my life.

When it comes to short-term decisions, I am impulsive AF. My Enneagram 7 persona takes over and I click purchase before you would finish reciting my credit card number. But, when it comes to big “long-term” decisions, I am an analytical buyer. I read reviews, reach out to previous buyers, and ask about 800 questions and probably still wouldn’t make a move…. Until I am ready months down the road.

So, in this case, I posted in Facebook groups asking for advice. I asked other designers in the industry if they had any insights or tips to make the transition easier to full-time entrepreneurship. I played the “what if” game with my best friend and fiancé probably once a week for 6 months straight. And I went back and forth with my own thoughts every single night.

Here are some tips that were given to me before making the full-time leap by other small business owners:

  • Gain control of your finances. Do a deep analysis of what desired annual income you want to bring in and calculate the expenses you have. Once you know that number, take inventory of the projects you are taking each month. If it’s not adding up to your desired amount, raise your pricing – and be confident on sales call to do just that.
  • Make sure all of your legal paperwork is signed, sealed, and delivered. Protect yourself against any risks, whether that be incorporating or purchasing business insurance.
  • Check your systems. Are they automated and working the way that you would like? Where can you save time and efficiency?
  • Have at least 6 months’ worth of savings in your bank account, just in case of a slow season or any other emergencies
  • Be booked out of projects for at least 2-4 months so that you have revenue coming in at least for one upcoming quarter
  • Consistently be able to bring in your desired monthly revenue (post-expenses) for at least 3 months before quitting

I did some of these things, but certainly not all. Because I knew that deep down, even if I was 120% prepared that it would still not prepare me for the inevitable or “the unknown”.

Which leads me to…

Mindset Shifts

The biggest misconception that people have (especially in this social media era) is that everything is an overnight success, including cultivating our mindset.

I will admit: My mindset has dramatically shifted and expanded from when I launched a year and a half ago till now, mostly because of the investments I made in my business, specifically on a business coach as well as in a mastermind. There were eight months of intense questioning, reflecting, journaling, that went on. Mostly about my deep-rooted self-trust issues and the self-limiting beliefs I held against myself. And when I stepped out of my “bubble” and looked inwards, I realized what I was holding on for.

Questions that propelled my mindset forward:

  1. What does failure mean to me? Why does it affect me?
  2. If money wasn’t a factor, what is success?
  3. What does running a business truly mean? What impact do I want to create?
  4. Whose permission am I looking for?
  5. What is the best possible scenario that could happen?
  6. What is the worst possible scenario that could happen?
  7. If the worst happened, what are three things that I could do to rectify that?

Once I was able to answer those questions HONESTLY, I began to feel more confident and true to myself. The weight began to feel lighter on my shoulders. It started to reflect in everything that I do in my business, which includes charging prices that reflected my work and building out client experiences that were aligned with who I am.

Related post: How To Overcome Imposter Syndrome

Making The Decision

While there might have been a lot of reflections (and back + forths) going on in the background, I didn’t fully make the actual decision to quit until closer to the end of last year during my rebrand launch. But I knew I was the only one holding myself back at this point and that if I truly want to create the life that I want, I need to make a bet on myself.

(Sorry to say but there is no secret formula or courage elixir here!)

The first thing I did before anything was to set a date… and then told people about it. Just so they could hold me accountable and have it feel *real*. I am grateful to those people because every chance they got, they encouraged me and reminded me how right this is. And how everything I have worked for has led me to this point — specifically.

Next, I took inventory of all of the things that would keep me busy and on track as I continue to build the business up. I had a couple of projects lined up but I knew it wasn’t going to be enough to sustain me in the long run if I suddenly had another slow season. I talked to my financé about all of the various scenarios and planned for it, especially since we recently bought a house and got engaged.

Lastly, I made a decision to talk to my close work friends about it before having “the conversation” with my boss… which ended up kind of feeling like a trial run. I have always been the type of person to avoid hard conversations (oh, the Cancer in me!!!) or to over-prepare for them. But because I was talking to my closest work colleagues, I felt that I was able to genuinely express myself and speak from my heart… which ultimately helped the big discussion go much smoother.

I am grateful to my team and my colleagues for being so supportive and excited for me. It truly reminded me how important it is to have a community rally behind you – something I knew I would miss making the transition into a full-time entrepreneur where I’d “lose” the opportunity to collaborate closely with colleagues every day.

Related post: 2021 Year In Review

Where am I now?

Well, it has been a month since I transition from my 9-5 to full time entrepreneurship… and I can say that a lot has changed but at the same time, not really. I definitely enjoy the freedom of creating my own schedule each day, though, I am realizing more and more every day what my working style is and the skills I need to continue to cultivate as a full-time entrepreneur.

If you have been toying with the idea of making the transition from your 9-5 to full-time entrepreneurship, I want to let you know that you are more than capable and that you are going to wildly succeed. It just takes you to believe in that.

And of course, if you ever need a sounding board… or someone to cheer you on or hold you accountable, I am just a message away and would be more than happy to do just that. Making the leap is not as easy as it sounds but with the right people surrounding you, it makes the choice just a little bit easier.

If you have any other questions about making the leap, drop them below and I’d be glad to share!


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