Have you ever had a tricky work question you can’t stop agonizing about or a professional decision that needs to be made now, with little regard for your 9-to-5 work hours? Work things can have a big impact on your personal happiness and that’s where the lines between self-care and professional development can start to blur.

That said, it’s no wonder that when we asked what you wanted to see more of from GNI, one of the most common answers was workplace resources. When work things become life things, they can weigh on us at all hours – even on weekends when we should be doing our best lounging. With that in mind, we’d like to welcome you to the GNI Water Cooler – a place to chat about the work things you’re looking to take care of in the name of self-care. We’ll be rolling out the Water Cooler as an ongoing weekly series.

This week, we’re chatting with two PR pros and friends-of-GNI Alex Daly and Ally Bruschi of Daly, to get their take on how to handle some workplace questions you’ve sent our way. But first, a bit about them!

Alex is the founder of Daly, a PR, crowdfunding, and events agency. She also happens to be the Crowdsourceress, having helped several Kickstarter campaigns gain massive success in the past few years, raising a total of over $20M from 100,000 people worldwide. She's also a member of the Forbes 30 Under 30 class of 2016 — nbd.

Ally is the PR Manager at Daly, where she takes pride in creating powerful, well-crafted messages for the companies, products, and people that inspire her. Before joining Daly, she worked as a book publicist, but now she works to secure features for her clients in everything from The New York Times and The Atlantic to Oprah’s Super Soul Sunday and national NPR shows.

Here’s the advice Alex and Ally have for this week’s theme – starting something new, whether that’s a company or career path. ✨

Q: I am preparing to move to the Caribbean for two years in August (my hubby got into med school down there) and my employer is totally kickass and is hoping to make the working remote thing a thing. I have very little experience in the realm of working remotely, other than freelance graphic design and marketing gigs I pick up on the side. I will be working from home to add another layer in there. I’m writing to find out your best tips and tricks of the trade for working remotely, how to stay on task and engaged without feeling too much like a hermit, and so on.

Alex: Your employer sounds awesome! I travel a lot for work, and also enjoy working remotely when I need to get necessary headspace, so I have good experience with this.

First off, when you work remotely, it’s very easy to lose sight of a proper schedule. I would suggest carving out your work time and sticking to it. And even though you will be working from home and not in an office, don’t roll out of bed and work in your pajamas! In fact, get ready as if you have a day at the office ahead of you and be sure to create a special little workstation for yourself.

Creating this environment will allow you to plug in and then plug out at the end of the work day. Otherwise, your work and free time might start to blend together in an unproductive way.

I would also try to find a cafe or co-working space that you can work from occasionally, instead of planning to work from home every day. Otherwise, you might get lonely very quickly. Being outside of your living space will allow you to feel part of a community!

Q: I want to start a business more and more every day but I’ve been stuck for a few years now on finding a good idea. I keep running into stories in my head like I don’t have enough money to start something of my own or I don’t have the right connections or I don’t know what I have to offer. Nothing I’ve tried on has felt right yet so my question is: How do you get clear on who your audience is and then where the heck do you start?

Alex: I can say with confidence that no time will ever feel like the right time. I never had an “aha!” moment. At one point you need to ignore the stories in your head and just dive right in!

Right now, it would be helpful for you to find a mentor to help bounce ideas off of. As I was building my company, I asked so.many.questions. It was the only way for me to find my footing. You could also hire a career coach on an hourly basis who could offer professional advice and help you carve out a business plan. I am currently working with a consultant (Ask Holly How) who would be a great resource once you start your new venture. She has offered excellent foundational support, such as creating a mission statement, projections, and more.

On top of asking all the questions, it took a lot of experimenting and hard work before I got to where I am today. I worked in magazines, and then in documentaries, and then ended up in the crazy world of crowdfunding. I found lots of success in crowdfunding, but there was no playbook for me to follow!

I built a crowdfunding consultancy from scratch without any background in PR, business, or crowdfunding, and I always had to stay quick on my feet. The experience was not linear, but I learned to adapt by always keeping my focus on what the best next step was for myself, and for my company. For example, a few years into running my consultancy, clients started asking our team for ongoing PR support, so we went through a big evolution, and began offering longer term engagements for our clients. That’s where we are today.

I use this journey as a positive – my background in film and writing, and my bootstrapping spirit, has made us a diverse team with a hustler attitude. It wasn’t a conventional journey – in fact, it was pretty bumpy (I also experienced feelings of frustration and self-doubt at times), but in the end, it got me to where I am today with Daly.

Q: How do you jump from one industry to another – especially if you know your skillsets are transferable, but that may not be obvious to your potential employer?

Ally: I’m a strong believer in the power of a thoughtful, personalized cover letter, because this is often the first (and sometimes only) shot that you get, as an applicant, to convince your prospective employer that the skills you’ve developed from your past professional experiences would make you a killer member of their team. Rather than using your cover letter as a space to reiterate the highlight reel of your resume, use it to highlight the top transferable skills that you would bring from your current role and industry to your desired, future one. Be ultra-specific!

I faced this exact challenge last year when I sought to move out of my previous job at a large corporate company, into my current one at a small startup. While the job title I was pursuing was similar to the one I held at my previous employer, I used my cover letter (sent in the body of an email, which is my preferred method over attaching a cover letter as a document!) as a chance to explain exactly how the key skills and relationships I’d formed in my then-current job would help me contribute to the company I wanted to work at. Specifics are key! The more your cover letter reads like a heartfelt note over an edited template, the better.

I also highly recommend going on informal, informational interviews with as many people as you can in the industry and companies that you want to break into!

Q: Let’s say you’ve worked at a startup, or generally any small to mid-sized businesses for most of your career, as I have. A common thread through all of these jobs (whether it’s working in fancy coffee, or data analytics) is that talented folks become a jill-of-all-trades and “wear many hats” to keep everything moving smoothly. When you find yourself in this position, how do you specialize and focus your career? Even more importantly, how do you choose a focus when you may own multiple roles in your current position?

Alex: I love working with people who are multi-faceted, and find this to be a real plus! Companies these days are constantly changing, and being able to offer flexible, agile skills is something you should sell as a positive attribute.

That said, if you are looking for focus, consider which of your skills you like using the most. Is it creative? Managerial? Leadership? Strategy? Then try to find a role that fits that specific skill. Being able to flex those muscles will hopefully help you feel more focused and fulfilled, and you will also be able to support your team or company with the additional hats you can wear!

Got any work + self-care questions you’d like us to answer in the next GNI Water Cooler? Ask them in the comments below. 👇✨

Images by Pheobe Cheong.