How to overcome obstacles that your corporate job didn’t prepare you for

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Image from Dreamwriters

hen I left my corporate job to start my own business, I was prepared to leave the comforts of a well-established company to enjoy the struggles of becoming a bootstrapping solopreneur. With a lack of human and financial resources at my disposal, I knew that I would need to do many things on my own and I was more than willing to learn. Having worked on my business for close to a year now, what I found was that acquiring new skills, while time-consuming, is actually the easy (or easier) part. The difficulty lies in navigating through the uncertainty and obstacles in your path without a safety net. Below are some of my key learnings:

  • If what you need to learn is way out of your skillset, then it’s time to outsource — The company I am trying to build is called Dreamwriters, a self-publishing platform for young writers and artists. There are some unique functionalities to the site which requires a custom build. In an effort to save money, I toyed with the idea of coding the platform on my own, and even took some online courses offered by LinkedIn. Then I remembered, I have zero technical skills to speak of, and I absolutely hated the computer science classes I took in school. Building this thing from scratch would have taken me an eternity. I decided to hire an agency to help me. Best…decision…ever…I now look back and laugh at my naivete.
  • At some point, you just need to make a decision — For the less technical stuff, I opted to learn these new skills on my own. I went to my trusted friend, Google, and searched for solutions for my various needs. Boy, oh boy, the world had surely passed me by while I was in my corporate bubble. Need a domain name? Try,, or Want to build a simple website? See LeadPages, SquareSpace, and Wix. Looking for a web host? How about AWS, BlueHost, or HostGator? Want team UI/UX team collaboration tools? See Miro, Axshare, and Figma to name a few. The abundance of choice and the amount of research required made me want to pull my hair out. The truth is, all of the options are likely just as good or bad. In the end, test a few of them out and if the one you prefer fits within the budget you set, just pick one and march forward.
  • When in doubt, ask your friends for help — At some point, I hope to reach out to media and influencers to help me spread the word about Dreamwriters. No longer armed with a communications department, I reached out to a few friends who do this for a living. They coached me on the key documents to create for the press and helped me edit my business fact sheet, bio, pitch notes, and presentation. I am so grateful for the help because my original versions were such drivel. You’ll find that your friends, and even strangers, are more than willing to offer advice. So don’t be afraid to ask.
  • Leverage your experience and trust yourself — I was a marketing professional in my previous life, which meant that I normally hired agencies to help me create campaigns. I relied on them so much that I realized I never actually executed anything on my own. Recently, I wanted to create a Kickstarter video for Dreamwriters. Given the costs, I knew that hiring an advertising agency was out of the question, but why would I hire when marketing is in my wheelhouse? I ended up developing the concept for the video, creating storyboards that looked like chicken scratch, hiring a freelancer through LinkedIn, booking a venue, and buying all the props myself. I was scared but I got the job done. For those who have worked in corporate and are looking to make a jump into entrepreneur land, don’t discount the experience you already have (discussed more in this post).

If I were to summarize the above, I would say that it boils down to one thing — overcoming fear. Whether you are making a decision to hire, purchasing a service, asking for help, or working on a task yourself, it’s the fear of making the wrong choice that keeps you from making a decision. While I still struggle with this, it has become easier over time, and I have grown personally and professionally as a result.


Published By Amy Wong

Amy is the Founder of Dreamwriters, a self-publishing platform for young creative writers and artists. Follow us on Facebook and Instagram too!

Originally published at

The founder of Dreamwriters, a self-publishing platform for young creative writers and artists.

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