Interview: John Doherty

John Doherty is a digital marketing professional by trade, but these days he is more of a software founder at Credo, a marketplace founded in 2013 with the objective of connecting the best digital marketing consultants with companies that need their services. You can find him on his personal website,  and also on Twitter.

1. How did you started working remotely? How did you do the switch?John Doherty remoter

I started working for myself in October 2015 after experiencing some career turbulence with my last employer. I was already planning my exit to start my own company, so this simply sped up the timeline and gave me a bit of financial runway to get my company off the ground.

So I started working from home then, and from there figured out how I work best. I’ve actually run a lot of experiments on myself to figure out where and when I work best. For example, I now know that I am most aware and able to do sales calls in the morning so I can then retreat to a coffee shop for the afternoon to work on other tasks.

2. Which are the main advantages that you find that remote work has?

In a word, remote work is freedom. Since I started working for myself, I’ve worked from seven different countries, twelve states, and literally flew around the world and traveled with my wife for three and a half weeks.

Remote work allows me the freedom to work from wherever I want and whenever I want. I’m not tied to an office space and therefore a lease, so I can work from the place that best suits my mood and the projects that I need to get done.

I am a huge believer in not living a “deferred life”. Meaning, I do not want to live a life I do not like now in order to hopefully live the life I do want to live later. I want both right now – a career and the life I want. This is what remote working for yourself does.

3. Do you think you have disadvantages or that you’re missing something by working remotely?

There are a few disadvantages to working remotely.

Firstly, you can miss the in-person interactions with others that are so valuable to building relationships. While most of my professional network is around the country and the world and we communicate via Twitter and email, I still deeply value times seeing them in person at conferences and such.

Secondly, when you work remotely and something goes wrong (such as recently my computer quit working), you alone are responsible for it. I undervalued how incredible it was to have IT support at my last few jobs.

Finally, it can be incredibly hard to focus while working remotely when you are in new places or around people who are not working like you do – whenever duty calls. Sometimes you can feel like you are missing out on cool things happening around you, so it’s important to manage your own psychology and think of work time as work time and play time as play time, and to then separate yourself from work from time to time while traveling so you can enjoy where you are.

4. From which cities or countries have you worked from since you have become remote? Which has been your favorite one?

Since September 2015, I have worked from Seattle WA, Portland OR, San Diego CA, San Francisco CA, Lake Tahoe CA, Salt Lake City UT, New York City, Denver CO, Austin TX, Mexico, Prague, Vienna, Budapest, and Tokyo. Before the end of 2016 I will also work from Costa Rica.

2017 has more places on the books as well!

5. From which type of place do you prefer to work from? Coworking spaces, coffee shops or others? Do you have any specific place?

I like to break up my day so that I am in places where I can concentrate depending on the task. Because I do sales calls as well as client calls and also record different forms of multimedia for my customers, I often need to be in a quiet place such as my home office or living room. When traveling, I’ll often work from my hotel room or AirBNB. I’m lucky in that I do not have a Fear Of Missing Out (FOMO) when traveling, so it’s fairly easy for me to concentrate.

I also break up my day with morning sales and client calls, while afternoons are usually reserved for product work and writing/marketing. So in the afternoons I will often go work from a coffee shop or similar place that I am familiar with. I like to find places that feel comfortable and are familiar, where I also know that I will have reliable wifi and will be able to find a comfortable place to sit.

I find that when I am in a new city and do not have this, it is much harder to get into deep work mode.

6. Which places would you like to travel to while working remotely or working from?

I’d like to do a few months in a tropical location, like Thailand or Costa Rica, living by the beach and living that true “digital nomad” lifestyle. I’d also like to spend a winter in the mountains or a mountain/ski town where I’d ski in the mornings and work in the afternoons/evenings.

7. What would you say to the companies that don’t believe on hiring employees who work remotely?

I’d say that these companies are missing out on fantastic talent by being so location-oriented. I also think that having remote workers is great for companies because it forces them to get good at communication and managing projects. When you’re in the same office as someone, it is easy to assume that you are on the same page as them on projects because you’ve seen them face to face recently.

This doesn’t happen in remote environments, so once you figure out your workflow for remote projects, they tend to go smoother than when in the same office.

8. Which tools do you use to work remotely?

The tools I use to organize my life are:

  • Google Apps and Hangouts
  • Google Docs
  • Zoom (for international conference calls)
  • Trello (to organize my business and projects)
  • (bookkeeping)

I use Google Calendar and Calendly liberally for scheduling meetings, though these have challenges when you are on a very different timezone than the person you are meeting with.

9. How do you manage your business and taxes as a remote working professional?

I do have a permanent US address and thus those are the state taxes that I pay. I also do not travel nearly enough to claim residency somewhere other than the US, so I simply pay US federal taxes.

10. What advice would you give to people looking to work remotely and companies doing the remote switch?

Transition into it slowly. As you begin to spend more and more time remote, or have more employees remote, you will start to learn a lot about your own work habits or company culture. This will inevitably mean a few things:

  • Things will break and you will need to fix them (such as communication).
  • Some employees will thrive and others will not do as well.
  • You will need to establish new guidelines for work hours according to your culture (for example, some remote companies have certain hours during the day where everyone needs to be online).
  • You will learn a lot about yourself and how you get your best work done.

I recommend that you start off varying your day between different locations such as your living room, a home office, and coffee shops. You’ll quickly learn where you get the most work done, and which kinds of work are best for which environments. You can optimize from there.

Finally, recognize that when you first go remote you will likely get less work done than you did working in an office fulltime. Any change of scenery does this, but having complete control over your location and scenery especially does it. So cut back on your workload a bit until you are comfortable with working remotely and learn how to get things done.


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