The biggest difficulties I faced at the beginning of a career as an independent designer are fairly common I believe. First is the catch-22 of building a portfolio of real work: I wanted to pursue clients I was excited about and which I would be proud to share in my portfolio, but without already having examples of similar work I struggled to build the portfolio which would appeal to them. Second is the challenge of learning how to run a business: how to manage a design process which wouldn’t constantly creep outside the budget, or how to demand more from the client when it did; how to manage a client’s expectations, so that they feel invested in the process and complicit in the results, not to mention happy with the final product. These are difficulties I still face now as partner of a fledgling design struggling to scale up and evolve, although thankfully I have a lot more experience and knowledge which makes me more confident in tackling these challenges.

In order to not get hired, a young designer should have no idea of who they are speaking to, how to address them, or what they are trying to say. They should either copy overly-formal cover letter templates beginning with “Dear Sir or Madame”,  or write an email on their iPhone opening with “Yo guys”,  and throw spelling and grammar out the window. It helps if they don’t really know what they want or how they would be relevant to the potential employer. Although, if you really didn’t want to get hired, the best method would probably be to have an absolutely hopeless design portfolio.

I wish I knew a lot more about running a business. This might not be the same for a designer working for someone else, but having worked independently for the majority of my career thus far, designing has always been the easy part; the subtleties of successfully running a business has never come naturally.

— Track the time you spend working. All of it, always.
— Tell your client exactly what they are getting for the price they are paying (how many options, how many revisions, etc).
— Make clients sign contracts and pay deposits. They will take your time seriously.
— Know how much you want to work, and try not to work more (it’s not easy, but try).

The last thing I want to do after working all day is read about design, but here are few books which I found impacted the way I think about design, and the role of a designer: The Society of the Spectacle  by Guy Debord
This book is a brief aphoristic critique of modernity and public artifice, especially in advertising and the arts. It is useful as a designer to consider what it means to represent an idea as an image and what inverse consequences that may have on the subject being represented.
Art and Visual Perception: A Psychology of the Creative Eye  by Rudolf Arnheim
In this book Arnheim “describes the visual process that takes place when people create — or look at — works in the various arts, and explains how they organize visual material according to definite psychological laws”.
F.R. David, which is actually a publication by graphic designer Will Holder. I recommend this because it is a great example of what graphic design can be when it extends beyond the surface to compile a beautifully considered artifact of art and ideas.