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Graphic Designer | Will

In the beginning.

Worked in tech startups for about 11 years as operations manager, Event Manager (and a multitude of other ‘hats’ inevitably required when working in a startup scenario).

Worked my way up starting as temp tech-support to operations manager over the course of 2 years, identifying gaps in processes or areas that could be optimized > then just did the work and ended up taking ownership of more and more sections of the company. Nobody assigned me these new roles, I just saw what needed doing and started doing it. 


Learning along the journey.

Taught myself constantly, rarely if ever in a class/course environment (the internet is an epic source of self improvement - no excuses).

Self taught: SalesForce Admin and customization, Zendesk admin, design & marketing, support documentation, partner program development, business development & much, much more.Hosted weekly web events, mix of sales, education, partner programs etc.

Learned a LOT and was honed into a potent tool for getting projects done but it was a real soul-sucking experience in the end. 

Will’s a-ha moment.

I was burnt out and stressed to the point of medical concern. Took the opportunity to transition to freelance full time as a graphic designer and it was not a seamless transition (a story common to many who make this transition as I well know from my hosted events).

Finding my way as a freelancer took the support of trusted entities in my personal life as well as various professional connections who were amazing at providing perspective and support as I fumbled my way through the transition.

What didn’t work in the beginning?

I was not smart about using the resources available to me as an Upwork freelancer. I never attended educational events. I rarely read any support materials on how best to succeed in this new space.

I made pretty much every mistake you can on my journey to success in this space, as a result-I learned a BUNCH and am super passionate about sharing these awesome resources and nuggets of wisdom with the community at large. If I would have attended educational events and leveraged the abundance of resources Upwork provides, my timeline to finding a stable and successful level of work as a freelancer would have been measured in a few weeks rather than half a year. I know this because I’ve worked closely with friends/professional relationships making this same transition and watched them do it the right way and quickly get things dialed in.

Making the journey work.

Once I began work as an ambassador for Upwork, hosting educational events and interviews for the community, I quickly realized I have a true passion for this - educating and supporting the success of our community and enabling people to find the joy and freedom of freelancing and taking ownership of their experience. I moved into Upwork Event Manager role in a similar way I moved up in my tech startup roles - Find where the gaps are > identify if I have skills/ability to contribute to the solution > dive in and see how it goes. I organically lean more towards a forgiveness rather than permission model, and fortunately I find it typically goes well so long as I'm approaching it from an uplifting and objective focused viewpoint - not a self-serving motivation.

I have so much fun and fulfillment hosting a wide array of events for Upwork communities. The commentary and feedback I get from attendees who are experiencing much of the same concerns, growing pains, struggles etc as I did when growing my independent business makes all the effort that goes into crafting these events totally worth it.

Career story conclusion.

If I can contribute in even the smallest way to assisting a fellow human find their bliss and freedom in being a freelancer, then I measure that as success!

Connect With Will on Upwork 

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