This is How I Started a Successful Business Straight Out of School

Gillian Sisley

Are you sure you’re ready for the reality check of what it takes?

Photo by Logan Isbell on Unsplash

Whether you’re a millennial who is in the midst of your post-secondary education, or you’re a more experienced professional who’s been in the workforce for a while and are considering going back to school for a completely different industry, this advice will apply to you.


Let’s have a candid conversation: the job market right now is total shite.


If you’re like I was, with university graduation staring you terrifyingly in the face, you’re probably wondering, “How the hell am I going to make all of this school and all of this debt worth it once I’m in the workforce?”

Great question. You’re probably also super concerned about finding a job and career that’s fulfilling and doesn't feel like it’s sucking out every ounce of your soul.

Been there, too.

Which is exactly why I approached my career in a more unconventional way.

I asked myself a bold and pretty scary question:

If I can’t find the work I want… why not create it?

And that's exactly what I did.

Before even walking across the stage to accept my diploma, following 5 years of post-secondary education, I was laying the groundwork to be my own boss and start my own business as soon as I graduated.

If you’re wondering how to make that happen for yourself, the following is the best advice I can give you.

Strap in (and maybe grab a glass of wine or an Old Fashioned), because this is going to be a shocking reality check.

You ready? Let’s dive in:

Choose a post-secondary program that isn’t just theory-based.

If you’re already out of school, this doesn’t mean you’re screwed.

But, it could mean, if an undergrad just won’t cut it for the career you want, that you may want to consider going back to college. Sorry.

So, don't get me wrong, I loved university. Those four years were incredible times of growth and life lessons for me.

I wouldn’t change that time for the world, and without my undergraduate degree, I wouldn’t have been able to then study an Advanced Diploma in Public Relations (which was the best career choice I could have ever made for myself, by far.)

The problem is, especially with an undergrad, those four years are stocked full of theory and sitting in classes and taking notes. So much so, that by the end of those four years, you walk out of your graduation ceremony and think, “Well shit. What the hell am I even going to do with my life? What have I even learned to prepare me for the real world?

I was supposed to have things figured out by then too, but I didn’t! What the hell was I going to do with a double major in French Literature and International Development, and a Minor in Chinese? My choices were obviously pretty f*cking slim.

So I started asking around, and heard about this really great program that had a phenomenal reputation in my city. It was an advanced diploma program, which required an undergraduate degree (yay! Those four years weren’t in vain!)

I applied and got early acceptance. As soon as I started the program, I was so incredibly impressed and relieved by how hands-on and practical the community college experience was compared to my university experience.

After that 1-year advanced program, I stepped into the workforce with confidence and assurance in knowing what I needed to do to succeed.

Including indirectly knowing exactly what to do to start a business.

Make your “beginning career mistakes” in your program, not in the workforce.

One of the biggest plus sides to hands-on education is that it gives you a safe space to make your mistakes during the program, rather than once you’re in your entry-level job.

Use your program as a chance to experiment and test your grit.

There were several assignments when I wasn’t exactly sure what the “right way” to do it was. I had an idea that could sink or swim, and I always chose the option to be bold and take a risk.

Being bold almost always worked out for me.

And in the times that it didn’t, I was still relieved that I’d taken the risk. Because these lessons of experimentation and boldness are ones you’re going to learn eventually.

Trust me when I say, it’s within your best interest to make your career mistakes in the safety of the classroom with instructors who are committed to your continued growth and education, rather than in the workplace as a new employee, where your employer is going to judge you and see less value in you for the mistakes you’re bound to make at some point, anyway.

Mistakes are unavoidable, so just brush away the fear, and intentionally make your mistakes in an academic setting where the worst thing that can happen is losing marks on your grade rather than losing marks on your reputation and competence as an employee.

Prioritize networking and making connections over getting straight As.

I wasn’t looking to be top of the class. Truth of the matter was, the student who got straight As and the student who got straight B-s were still ending up with the same diploma at the end of the year. Employers are rarely interested in seeing your post-secondary transcripts — they just care that you have the credentials.

I didn’t care about As as much as I cared about finishing the program with real, quality connections in the workforce. So I invested a lot of time into networking and meeting active professionals.

When I did meet them, I made the most out of our time together. I asked important questions, dug into their most valuable advice, and prompted insights which I wouldn’t have otherwise gotten if I didn’t put in the extra effort to network, ask them out for a coffee to pick their brain and learn more.

I figured out pretty early on that many people were more than happy to grab a coffee with me and give me their insights as a mentor. All I had to do was ask.

Keep in mind that professionals in a career which you’re interested in still remember how hard it was to get to where they’re at, and they’re often happy to pay it forward and assist another newbie on their journey to success.

There are connections from back then who are still referring clients to me three years later. So yeah, networking was a very good choice on my part and positively affected me for years to come.

Get practical experience for your resume.

I wanted something more practical than As — I wanted hands-on experience.

When we started the program, the director (who is still a mentor of mine), told us to say goodbye to friends and family, and to quit our part-time jobs, because we were going to be working 60+ hours a week and wouldn’t have time for anything else in life. I remember hearing this at our orientation and basically shitting myself out of fear.

Several months after gradutating, I would admit to the program director that I, in fact, didn’t quit my part-time job — instead, at the height of my busy schedule, I was working 70+ hour weeks with three part-time jobs and three on-going volunteer positions.

She was horrified, and couldn’t understand how I didn’t have an emotional breakdown. Truth was, I was just incredibly hungry to succeed and start my career on the best foot possible.

2/3 of those part-time jobs were related to either freelancing or fine-tuning my professional skills (one of those employers would end up becoming one of my clients once I graduated). All three of my volunteer positions were specifically related to public relations, and in each one I had a supervisor who I worked very closely with and was building a solid relationship with (one of those supervisors is also now one of my closest friends!).

I had absolutely no PR experience before the program. There were 30 of us graduating and going into the workforce in the spring — I needed more than just a diploma, I need an edge.

And I worked my ass off for that edge.

If you have a work-term, avoid the competitively small options within the program and find your own ideal fit.

At the beginning of a small program, you will often find things are all hunky-dory. Everyone is friendly, you’re all suffering together in harmony, and all is well.

And then, second semester hits, and it’s time to lock-down work-terms.

Man oh man, do the claws ever come out during the “work-term hustle”. It was basically the Hunger Games in real life.

Being that we were in a program with a very good reputation in our city, companies and organizations would line up with work-term options. There was a pool of about 40+ work-term job descriptions for 30 some students, so everyone was going to get one, regardless.

But I wasn’t interested in participating in the competitive clawfest (I hate competition, and actually actively avoid it whenever I can).

Instead, I broke out on my own, very, very early into the program. I was thinking about work-term possibilities one month in, about five months before anyone else in my program even considered what kind of work-term they would be interested in.

I did my research, and decided that I wanted to try and lock down a work-term at a very reputable marketing and PR agency downtown. I got in touch with a contact who then connected me to one of the agency partners, the head of PR at the firm.

That was my “in”.

The partner kindly met with me, specifically because I had shown initiative and been upfront about my intentions. He then introduced me to the social media manager (a past grad of my program, actually), and she and I arranged coffee.

From our first coffee date, about a week later, she thought I was a great fit and was happy to arrange a possible intern position with her as my supervisor for the month of my work-term, granted my grades stay up and everything was approved.

Even though she had agreed to facilitate my work-term at the agency from our first meeting, it still took 5 months to make it a possibility.

From nurturing that relationship to visiting their office several times to many emails back and forth coordinating the entire thing, even though I started 5 months before my classmates in my work-term hunt, I still got hired the exact same time as the rest of them.

For my classmates, the process was maybe 2–3 weeks from interview to hire. For me, it was a 5-month-long, active effort.

I created more work for myself in an already busy program, sure. But it was so incredibly worth it. For one, my classmates and program director couldn’t believe I’d nabbed a work-term at this agency — but more importantly, that experience opened far more doors into my career than I could even begin to explain. Many of my classmates walked away from their work-terms with a sour or a mediocre taste in their mouths, and they didn’t even make a penny.

I walked away with a $1,000 honorarium, and a community of mentors and colleagues who were deeply invested in my career and were happy to help me in my future success. This is all because I put in the necessary leg work to make those relationships authentic, deep and meaningful. And I had been doing so for months and months and months.

They even took me on for an additional month through a freelance contract following the end of my work-term.

I would use the $1,000 honorarium to fund the startup of my social media company.

I believe everything happens for a reason, but I also believe that we have to actively make our successes happen for ourselves.

If we’re inactive participants in our own lives, we have no right to complain or be shocked when all we are greeted with is more inactivity, and finding ourselves in the exact same place we started.

Final word.

All this to be said, this post can be summarized into one finite statement:

Don’t settle for the mediocre, actively make the exceptional happen for yourself.

Be willing to put in the work it takes, with absolutely no pay to expect. Investing in your future, particularly when you’re just coming into your career, will not show fruit immediately. That can be discouraging, but you must have faith in the fact that you’re building a foundation to success through your active, intentional efforts.

Success is not just given to you — it’s rewarded to you in exchange for unbreakable determination, laser-focus grit and undeniable hard work.

Keep this in mind: while you may have 2, 3, 4+ years of school under your belt, society and life don’t owe you a single. damn. thing. You’re not special. But if you’re willing to do the work to get yourself to where you want to be, you’ll sure as hell feel special.

But then again, you don’t have to listen to me or take any of my advice to heart —

I’m just a 25-year-old successful entrepreneur with 5 years of post-secondary school who started her business at 22 and was able to buy a house (entirely on her own, not with a partner) at 24.

So what the hell do I know?

Comments / 0

Published by

Online solopreneur. Tea drinker. Committed optimist. I write about trending news, viral Reddit content, and anything else that tickles my fancy.


More from Gillian Sisley

Comments / 0