Leaving a salaried corporate job to pursue your passion project, freelance, or launch your own business is an intimidating decision, to say the least. It can feel risky, downright terrifying, and even irresponsible to leave the security of a steady paycheck for the unknown. But for many creative, entrepreneurial-minded people – including us – taking the leap from the corporate world to self employment can be the best decision for their career and overall happiness.

This is a common question I get asked on blogger panels and from friends in different fields considering taking the leap.  I thought it would be fun to share my personal story of leaving corporate fashion to pursue HOUSE of HARPER exclusively and then share our tips on what to consider before making the leap yourself.

For me, my ‘why’ for launching my own business was because I wanted to start a family and I wanted to have a better work-life balance for my family.  Before HOUSE of HARPER, I was a Buyer at Neiman Marcus and then Gilt Groupe.  The demands of the job included late hours at the office and travel which would ultimately keep me away from my future family.  I loved my job and the fashion industry, but for me – I knew the job didn’t align with my vision of how I wanted to parent my future children.

In 2011, while I was working at Gilt, I was cast to host a new video project we were testing, Gilt TV.  As the co-host, I got to meet and work with other influencers and this is what first got me thinking about starting my own blog.  The thought of using the knowledge and connections I had made from working in corporate fashion for nearly a decade and channeling that into my own creative space was exciting, but too risky to leave my career for. When Fred and I took a vacation to St. Lucia that spring, I bought the domain and started shooting content for the blog during our vacation.  (If you want a good laugh, click here and then go to March 2011.)  During the two years that followed, I continued to spend my nights and weekends shooting content, publishing articles and attending events on top of +10 hour work days at the office.  Fred was in business school at the time so both of our schedules were crazy.

Two years later, we were pregnant with Knox and I knew something would have to give.  I wouldn’t have time for Gilt, HOUSE of HARPER and being a mom.  So then the question became, what am I willing to give up? I had spent two years pouring my soul into HOUSE of HARPER during my free time and it was paying off.  HOUSE of HARPER was already providing financial support for our family and it had given me opportunities I had never imagined, like sitting down with Diane von Furstenberg to discuss the future of social media and influencers for the fashion industry. It was also challenging me to learn new skills while giving me the creative freedom you simply don’t have when working for a large company.  For these reasons, I wasn’t ready to give up on what I had built at HOUSE of HARPER.  It was time to let go of my stable, corporate job and paycheck to take a bet on myself and to focus on my new role as a mom.

Of course, coming to that decision brought on other important questions.  The next and perhaps most obvious being ‘What is the financial risk?’  Again, we were living in New York City at the time and a full-time nanny doesn’t come cheap.  When I took into consideration my salary at Gilt minus paying a full-time nanny, that became my financial goal for HOUSE of HARPER.  I wanted to have the financial benefit of continuing to work, but the freedom to work when Knox was napping or after his bedtime.  When I broke it down like this, it didn’t seem so risky after all.  I had already built a steady income from the blog and I felt confident that focusing on it more would allow me to continue to grow the income stream.  The fear of failure that I did have proved to be a good thing because it provided the motivation and adrenaline I needed to power through the challenges.

To be completely fair about discussing risk, I realize how lucky I am to also have a husband with a successful, steady job that provides insurance and benefits. I am very aware this leap would have been much more terrifying and risky if I were taking it alone.  (Major props to all the single ladies out there who are killing it and doing it all on their own merit!)  FMK has always been my biggest supporter, cheering me on and providing the confidence and security I need along the way.  However, as a family we had become accustomed to our dual incomes and way of life, so the risk and fears were real in the sense that had I not been able to produce the income we were accustomed to, we would have to find ways to cut back whether that be a lifestyle adjustment and/or less savings.  Not to mention the non financial risk that I could be pouring my time and energy into a project that didn’t pay off financially.

Fast forward five years later and I can wholeheartedly tell you that this was far and away the best decision for myself and my family.  Owning my own business has provided flexibility around my responsibilities as a mom, confidence in myself after growing and establishing a business into something from nothing, financial support for our family and, perhaps most surprisingly, it has even helped in our marriage.

Deciding to leave your job to work for yourself can result from a significant life change — like my decision to step away from being a buyer after having Knox. Other times, it is simply a matter of finally being ready to jump after months or maybe years of debating it. There may never be a clearly defined “right time”, and there will always be unknowns on the other side, but there are ways to prepare and ensure that you are set up for success. If you’ve been considering leaving your job to wholeheartedly pursue your side hustle or passion project, read our five steps below to help you start moving in that direction!

Know Your Why

Daydreaming about the ins and outs of starting your own company is great, but it’s important to consider the motivations behind your vision. Are you starting a company that is filling a gap in the market and that you yourself would utilize? Are you creating a business that gives back to a larger cause? Or perhaps you want to freelance full-time because flexibility and work life balance are priorities for you. Write down why you are passionate about working for yourself and marinate on it for a while because this is what you will come back to time and time again when things get tough — because trust us, it will be a LOT of work! Make a list of the pros and cons for leaving your current position and then consider what is most important to you. Perhaps a con is working by yourself from home, but maybe that isn’t so bad when listed next to a pro of getting to work with clients who inspire you.  

Launch Your Passion Project as a Side Hustle

Before diving into your project with both feet, launch your venture as a side hustle and pursue it part-time outside of work hours. Create a business plan, map out your short term and long term goals, and start building your company. This will give you a better understanding of financial expectations and also confirm if this is really and truly what you want to do! If you do decide to make the leap, you’ll already have a solid foundation in place.  

Seek Advice from a Trusted Mentor

The decision to leave your job is ultimately up to you, but you don’t have to make the decision alone. In fact, we would highly recommend consulting someone, or multiple people, who you trust as mentors and advisors. This is a big decision, and you want to be sure that this path is right for you and that your business idea is supportive of your strengths and skill sets. A couple of side notes to go along with this point: first, we know that the ability to up and leave a secure job is not an option that is available to everyone, and we are very grateful to have had the opportunity. Secondly, if you are considering making this transition but are fearful of the unknowns, it’s important to remember that it doesn’t have to be a forever decision. As with accepting any new job, you aren’t committed to it forever, and if it’s not the right fit you can pursue something else. Adopting this perspective will help alleviate some of the anxiety and pressure you might be experiencing.

Schedule Lots of Networking Coffees

Working for yourself can seem daunting and isolating. How do you grow and learn if you don’t have a manager or driven coworkers? How do you always make the right decisions for your business without being able to consult others? The thing is, working for yourself doesn’t mean you have to rely on your own intuition for every decision. Build a network of people in a similar field by offering to treat them to coffee in exchange for their advice. Use LinkedIn and social channels as tools for reaching out to people you have never met (yes, we have done this and have received successful responses!). Establishing a support system of talented, ambitious people willing to offer guidance is invaluable for the success of your company. And it also makes the process a lot more enjoyable when you have a network of inspiring individuals to bounce ideas off of!

Build a Rainy Day Fund

If your side project isn’t lucrative yet, it’s of course a financial risk to put all of your eggs in one basket and say goodbye to a regular paycheck. While you’re gearing up to take the leap, be sure that you are saving up a rainy day fund that will help keep you afloat as you work your way towards a steady income. Financial experts suggest a three-to-six month cushion of living expenses, and you may want to adjust that amount based on how much you will be relying on savings when you start your venture.

Are you considering taking the leap to start your own company or join the freelance world? We’d love to hear your thoughts on how to prepare and what your biggest concerns are. Or maybe you have already done it, we would love to hear what worked for you!