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5 steps from an uninspiring career to fulfilling self-employment

Jaime Rose never knew what she wanted to do with her life and after a lot of trial and error she decided to go it alone and now has a portfolio career she loves and has just launched her latest venture The Escape List.

Throughout each milestone in my academic life, I was constantly waiting for the so this is what I want to do with my life moment. For me, it never came.

I eventually realized that the solution was that there was no solution. My career progression didn’t need to be as planned as I had always been told. I could actually try things out and see where they led, all the while with the knowledge in the back of my head that my end goal was to work for myself. And this is how I got there:

Step 1: The right idea, the wrong job

Quickly u-turning from misguided law school applications I was stuck as a graduate without a purpose. I decided to work in a field I was passionate about; property. After a successful internship, property search consultant I became, scouring London to buy houses for the rich (think Kirsty and Phil). I quickly realized that whilst my boss was fantastic and gave me control of my area of the business, the job wasn’t satiating some indefinable desires in me. Six months in I took the bold move and quit.

Despite the negative affect on my CV and people’s perceptions of me, I could never accept a job that didn’t make me happy; that had to be my guiding principle.

Step 2: Take two; still focusing on the passion thing

Now, unafraid to take control, I still didn’t know what to actually do aside from trying a different passion. I wrote speculatively to health food brands I admired and secured a summer field sales job at a small drinks company. Not the most glamorous job but I impressed them enough to secure a full time role as Head of UK Sales. I enjoyed the role, the challenge, the sector and especially the work environment. But after 18 months I was stuck in the rut of repetitive work and unfulfilled desires. I knew it was time once again to quit but this time safe in the knowledge that a lot of “work” existed outside of the well-trodden paths.

Step 3: Going it alone, albeit down an unexpected path

Spurred by experience of working in a small company, I finally took the gamble of setting up my own company with a friend, a hotel website I had been dreaming up for years. Problem was my lack of funds and relevant experience. Struggling with refining the idea, I took on some private tutoring jobs to earn money. My reputation spread and suddenly I had no time to work on my original idea. Initially, I resented the tutoring until I finally realized that I had inadvertently created a successful business. Embracing this I expanded my client list, hired more tutors and took on a business partner growing the company to one which generates over six figures and employs over 30 tutors.

I learnt that I had to embrace opportunities, not scorn them for interrupting my pre-conceived plans.

Step 4: Flying half way round the world

An unexpected move to Hong Kong with my husband had me leaving the tutoring in my business partner’s hands and with a desire to find a Hong Kong startup to sink my teeth into. I stumbled upon www.sassyhongkong.com and was brimming with ideas to grow the business. After a passionate speculative email, the two founders liked me and my ideas enough to invite me on board as an equity partner, looking after strategy and marketing. We have since merged with another company, quadrupled our database and are expanding through Asia. I work on Sassy according to my own terms and what’s more, it has provided me with an invaluable insight into the online world.

The last step in the journey, so far….

With tutoring and Sassy under control, the time was now perfect to focus on the hotel site. Refining the seedling of the initial idea, we spent 12 months building our site. The Escape List has just launched and I’m excited to see where it takes me.

It’s an affordable luxury UK hotel website. A simple and quick place to find inspiring, indulgent hotels around the country that don’t cost the earth. We have a fantastic initial collection of 40 properties and as we expand we want to stay true to our philosophy that you should want to stay in every place listed on the site and be able to afford to.

The Escape List only launched this month and we would love any feedback from fellow Esc The City members. And, we have a fantastic launch competition where you can win one of seven UK winter breaks, so don’t forget to check that out here.

So, here I am, 27 and working on three businesses. I work from home, manage my own time and work harder than ever. The money isn’t gushing in yet, but more importantly for me, the satisfaction and enjoyment are, so hopefully the money will follow. I realised it was never about what I wanted to do, but about how I wanted to feel.

  • Nikesh Ashar

    Hi Jaime

    This is a great example of what is possible if you put your mind to it. I am in a similar position to you – working in a deadend job and trying to escape!

    My entire career has been in the travel industry, buying hotel rooms and negotiating deals with everything from hotels to hostels around Europe.

    It would be great to know if we could speak about how we could help each other?

    I will leave it up to you.

    Thanks

    Nikesh

    • Jaime

      Hi Nikesh,

      Great that you have had the chance to build up such experience in the industry – makes it even more exciting where you can escape to when you decide to take the plunge!

      Would love to speak further – email me on jaime @ theescapelist.com

      Best,

      Jaime

  • http://www.jenidodson.com Jen

    Dear Jaime,

    Thank-you for sharing your story, inspirational ;o)

    Fly high angel and never stop following your heart. . . wishing you every success and happiness.

    Much love Jen x