We’re excited to introduce you to the always interesting and insightful Emilia Stypulkowska. We hope you’ll enjoy our conversation with Emilia below.
Emilia, thanks for taking the time to share your stories with us today. What do you think matters most in terms of achieving success?
I never imagined myself as an entrepreneur. As a kid, I was greatly inspired by artists and singers, but somewhere along the way – I learned that as an artist you have to be an entrepreneur. And I thought – well, I guess that’s not for me then! I enjoy a steady pay cheque.
But as I realized that my chosen career path did not actually give me the stability I needed and did not align with my values… I decided to step into entrepreneurship. I am now 5 years into running my practice as a career coach. I’ve learned what it takes to be successful in entrepreneurship and indeed, at any challenging goal you’ve chosen. I’d love to share what I’ve learned. I believe that you need the following to be successful:
1) A powerful why. There are going to be moments where you’re going to want to give up. In those moments, you need something to pull you forward. In the beginning, I didn’t have a clear vision of what I was moving toward. What I did have, was a clear vision of what I was moving away from. I did not want to work for a company that presented one set of external values, but a whole different set internally. I also did not want my income to rely on one source, and sometimes, one opinion of me (my boss’s). Those two things became powerful driving forces that allowed me to keep going even when my vision forward was murky and undefined.
2) The decision that you will succeed no matter what. When you decide that you will be successful no matter what obstacles enter your path, you will find that you can overcome anything. I often choose to include the words “no matter what” in an affirmation for the day because if I decide that I am going to have a great day – no matter what – then I don’t get discouraged when something doesn’t go my way. I have faith in my ability to pivot.
3) People who show you what is possible for you. When you’re working toward a challenging goal for the first time, you will inevitably doubt yourself. But when you see that someone else has succeeded at what you’d like to do – it gives you hope. Especially if you can see evidence of the fact that you and this person have some similarities. Maybe you both went to the same school, or you’re at a similar age… whatever it is, it can help you to imagine yourself accomplishing the same thing. In my 5 years as an entrepreneur, I’ve spent 3.5 years working with different coaches. Coaches that demonstrate what is possible for me and show me the way there. Aside from working with coaches, you can also connect with entrepreneurs through networking events to meet more people who show you what is possible for you.
4) The ability to identify your inner critic’s voice. Our inner critic is going to show up when we try to take big leaps and do things outside of our comfort zone. The bigger the goal, the louder the inner critic’s voice will be. But when you learn to identify your inner critic’s tactics, they lose some of their power over you. A book I always recommend is Playing Big by Tara Mohr. Her book teaches you about the inner critic so that you can learn to connect to your inner mentor.
5) Immense courage. If I had to boil my message down to just one thing – I would say it takes courage to be successful as an entrepreneur. This path will confront you with your biggest fears, your perceived flaws, as well as the dreams you’re scared to even imagine. You will have to face every belief you have buried in your subconscious. You will have to put yourself out there before you’re ready and risk looking like a foolish beginner or a fraud. As I say this – I understand that I’m not selling entrepreneurship very well – but the rewards are 10 times bigger than the risks. I love doing work that makes a massive impact on people’s lives. This work is meaningful to me because a person’s career is the foundation of everything else in their life. It dictates the amount of time, energy, and resources you have to pursue all of your personal goals.
A dream career is one that aligns with what motivates you, the things that light you up, the areas where you want to make an impact, and allows you to work from your zone of genius. This is what I’ve found through my work as an entrepreneur and a career coach. And this is what I hope you find too.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I entered the field of career coaching after spending 15 years navigating my own career. It was through my own experiences that I learned how to strategically market myself for positions that were progressively more aligned with my talents, motivations, and values. I overcame big setbacks and continued to catapult myself into bigger roles. I’ve now helped more than 60 clients from various industries and professions to identify a meaningful path and learn how to strategically market themselves.
I offer private and group coaching focused on both the internal work necessary to chart a meaningful career as well as the tactical and practical aspects of landing a dream job. This includes resume collaboration, interview prep, and offer negotiation. I help people figure out how to strategically market themselves for the type of role they want – to level up or to shift into a different role or industry.
I am most proud of my ability to help my clients tell their story and identify their zone of genius so that they can land jobs that give them more joy and more financial freedom.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
For the first 30-something years of my life, I focused solely on what I had to give to others. This way of thinking extended through my career, to my friendships, and to my romantic relationships. I drew confidence from how helpful I could be to other people. I prided myself on giving all of my time and energy to the people around me. The turning point came for me when the pandemic hit. All of a sudden, everyone was hunkering down and not requiring me to spend time with them or focus on their needs. For the first time, I felt free to focus on myself and my goals. I worked diligently on my health and my business. I was taking daily walks, doing yoga, reading, forging ahead with my business goals, and writing my book. The progress I made, made me feel confident in a new way. I started to draw confidence from my capabilities – not how helpful I was to other people. What I realized is that I could be an amazing friend, partner, and family member without solely focusing on other people. When I filled my own cup, and focused on my goals, I could give to others in meaningful doses and help others without depleting myself.

How did you build your audience on social media?
Building my presence on social media happened in stages. I had to keep playing with the edges of my comfort zone. Initially, I created an account on Instagram and posted stock images and quotes with some thoughts in the captions. Then I began to share videos. I felt comfortable on Instagram because the people who followed me, weren’t former colleagues from my first career. I wasn’t putting my new endeavor out in front of them. It took me a long time to post anything on Linkedin even though that’s where everyone told me I would easily be able to find clients. But I just kept honouring myself and my edges, working with coaches to build my confidence, and eventually I was ready to put myself out in front of the people I used to work with.
I think it was a good tactic because I didn’t go from 0 to 100. That’s what I recommend for anyone starting out too.
Contact Info:
- Website: www.sunnysideupcoaching.ca
- Instagram: @sunnysideup_coaching
- Linkedin: https://ca.linkedin.com/in/emilia-stypulkowska-53a48113

