The Wethos Collective -- Blog

Meet Phil Dearing, Co-Founder of Second Day: "Don't Choose Between Accelerating Your Career And Making Social Impact"

Posted by Alexis Nunez on Oct 11, 2018 12:54:29 PM
Alexis Nunez

For some of us, it’s hard. It’s hard to make the connection between what we’re good at, what excites us, what makes us money, what connects us with other people, what will make us grow/learn, and what a business or our world at large could truly benefit from that only we can contribute to.

The stars don’t have to align first for you to start bringing all of these desires together, and if you’re a freelancer or consultant you’ve probably already got a head start (how could you sell your services without knowing what you’re good at and what value you can add?).

Phil Dearing knew right before graduating school that he wanted to use his degree & skills to make a social impact, but didn’t want to sacrifice the ability to move up and learn quickly, perceivably the career growth and skill development that is only available in for-profit worlds. Fortunately he landed a job at Bridgespan, a strategic and fast-forward consultancy agency whose clients are tackling issues like health care and criminal justice reform in the nonprofit sector.

At the time, Phil didn’t think an organization like this was possible nor was he confident he’d get the job -- with only 10 people hired at Bridgespan on average out of 2,000 applicants, I don’t blame him! He realized that so many people we’re missing out on doing the work that he loved, either being intimidated by the process or having misconceptions on job growth, and as a result -- the nonprofit world was losing out on great talent that could accelerate their impact.

He co-founded Second Day in 2018 alongside Mariam Matin and Brigit Goebelbecker to help bridge this gap. Their resource guide and job board serves to show budding professionals that they do have more opportunities to develop careers in the social sector while developing skills that will help them to grow.

I sat down with Phil (we we're both sitting at the same time we logged into Google Hangouts, ok?) to first discuss his beginnings, pre-Second Day:

phil headshot linkedin-01

Phil: “As I was graduating, for-profit consultancy seemed like it had all of those things around skill development and quick career growth, but nonprofits were the areas and issues that i was really passionate about.

I didn’t feel like I wanted to make that trade-off. I struggle to get up in the morning unless I deeply believe in what I’m working on.

Fortunately I discovered that I could encompass both worlds. I work at a strategic consultancy firm but the issues I work on every day are in public health and criminal justice -- issues that I really care about deeply. I feel like I’ve been blessed to get both over the last few years.

I’ve encountered dozens if not hundreds of organizations that I think really do enable a life of purpose but also growth. Which is really the origins of Second Day, allowing other people to live in [their purpose] and to have opportunities like that.”


Alexis: What 3 skills have benefited you the most working in a nonprofit consultancy firm?

Phil: " 1. The ability to quickly understand where someone’s coming from and where you can be of the most value to them:

A lot of that comes from emotional intelligence, and some of that is asking the right questions. It’s astonishing to me, in consulting and in freelancing, just how doing the right piece of work is far more important than doing the wrong piece of work really well. Understanding [a business’] pain point, to figure out what they really need and why is a huge benefit that I’ve been working on a lot.


2. Having a sort of comparative advantage skillset:

You’re not going to sell much work unless this is true but whatever you’re offering. In my case, [what I offer] a lot of the time is detailed financial modeling, and I can do it in a way that they can’t necessarily do.

If you’re designing, you’re designing things in a way that they can't necessarily do. Really figure out what you are uniquely good at; invest in that skill set and make your expertise really clear.


3. If you’re in the position where you are trying to sell your work or build a community, I do think [you have to] take the time to invest in relationships:

Whether that’s keeping in touch with the people you’ve worked with previously, or going to events, going to things with friends of friends -- just sort of organically, not artificially, building relationships with a broad range of people generally leads to outside rewards and your own opportunities and development.”

A: What sense of community do you get from working up as a consultant in the nonprofit sector?

P: “I love being with people that see the unjust world we live in and are willing to commit their careers, which means the bulk of their time, to taking on those issues.

I really appreciate people that donate their time, donate their money --- but i think there’s something special about people who are willing to commit all in to making a change in the world. I feel like those are my people, those are the people i will go all out to support, and to help them be successful and live.

Tangibly that manifests with my friends in Boston who are also in the nonprofit space and we have conversations. I’ve been to YNPN events (Young Nonprofit Professionals Network) in Boston; I have a whole cohort of people at Bridgespan and we go to a number of different community events and engage in that way, and also through my church -- there’s a good number of folks that are engaged in social impact who I work closely with. We worked a part of the criminal justice reform bill that came thru in Massachusetts in the last few years.”


A: What have you benefited from most working with nonprofits? What impact are you most proud of making?

P: “I think for consulting and freelancing -- its really hard because often times you come in for a project, [and] maybe you see the impact of that project but more likely you probably lose touch and don’t ultimately see the results of your work and how it transformed the organization, or didn’t.

I think the benefit of working on a project basis is by working with a bunch of different organizations in a particular skill set or focus area, were able to get really, really, good at what we do. I’ve worked with a number of organizations in leading their strategic planning efforts and I know much better than the senior leaders at the organizations what it takes to construct a realistic business plan, engage with stakeholders across their network, build a detailed financial model -- all of these different pieces because I’ve been able to do it with multiple different nonprofits and foundations. With freelance ( wherever someone focuses on) -- being really good at what you do and using it with different organizations is of tremendous value to that organization because you are the expert in that skill set.”


Did you catch the first story in

Wethos x Second Day Series? :


About our partnership. is a platform enabling freelancers to collaborate around more meaningful work by forming teams with professionals in complementary skill sets. These teams are tackling large projects at some of biggest nonprofit organizations because they believe the people solving our toughest problems, deserve the best resources. Join Wethos Teams

Second Day is your go-to hub for building a social impact career. The organization offers resources to those who feel forced to choose between doing good for the world and doing good for themselves. Second Day offers users a personally curated job board that features top social impact jobs. Their team creates original content through company profiles, interviews, and professional development articles to give people a clearer window into the industry. Finally, the Second Day team is readily accessible to offer additional support and mentorship. Headquartered in New York, the team is spread across the United States. For more go to

Topics: Freelance, Freelancing, Wethos x Second Day, Impact, Professional Development