How did I get here?
In March of 2012, I quit my job. I had no plan (and really very few ideas!) for what I was going to do next. All I knew was that I was burned out and tired, and I needed to take a step back. I loved working at my charter school, still miss it some days, and still keep in touch with many of the people there.
I didn’t want to be a principal or an executive director. It didn’t align with either my interests or my skill set. Nor did I want that level of responsibility. I really didn’t know or understand what someone at the central office or at a charter management office did, and again, I was tired.
I was fortunate enough to live in a rent controlled apartment in San Francisco with no dependents, so, while living simply, I was able to take a bit of a break and do a little soul searching. I networked widely, and started talking to various people about what they did and how they got there. Many of these people mentioned they needed some help with some projects, so I helped them. I took some curriculum writing work that I found posted on Bay Area Edupreneurs. That client then connected me with some other clients. And it went from there.
In the last two years, I have started to take about two calls per month with people looking for the next step who want to pick my brain about how I got into this work. Several of those people told me I should write a blog, or at least write down all of the information in my head! So, here we are.
The consummate generalist
Before my work in education, I spent four years in tech startups. I managed a team of 20 or 30 people while I was still in my 20’s (ahh…the good old days of the late 90’s tech boom). I really had no idea what I was doing, but I learned a lot. I picked up a lot of design thinking, tech skills, and hiring practices, and while seeing a company go from 20 people to 800, and back down to 400, I saw an entire business cycle. This was where I honed my entrepreneurial spirit, and how I learned to be much more of a “startup person.” Before I worked at a charter school, I also spent four years at a large district high school, so I know some things about how district schools are run. At the charter, we were “teacher leaders” and then I was an actual school leader, and we had a “flat structure,” so I had my hands in a lot of tasks. I was technically the “Director of College Readiness” but also played the role of the Assistant Director of Curriculum and Instruction. I helped with hiring, gave input into budget, coached teachers, did discipline, ran intervention meetings, planned and ran PD, facilitated meetings, and planned field trips. We even created our own student sections! All of these experiences made me a generalist.
How do I decide to take on projects?
Because they are existing clients: see below, I do a lot of repeat business.
Because the work is interesting: sometimes you take on work you are passionate about.
Because it may lead to other work: sometimes clients are really well connected. Or, sometimes clients do a trial, a short project with you to see how you work together. Or, sometimes, they want you do to step #1 of a multistep project.
Because its a professional development opportunity: you constantly have to keep your skills fresh, and know what the new trends are in education.
Because I need the money: alas, such is life. Sometimes you take on projects just because you need cash.
Mostly, I am a curriculum and instruction person (in my heart I am still history teacher), and I design and launch (or expand) innovative schools. However, here’s a sample list of the types of work I do:
Writing curriculum and rubrics
Facilitating workshops and professional development
College Counseling (no scandals though!)
Reviewing grant applications
I often work for funders who are providing technical assistance to their grantees. Sometimes, people pay me to write reports they don’t want to write. I think if I focused on just 1–2 things, I might get a little bored, and I may miss out on opportunities.
My first love is designing and launching new schools, mostly because I can have my hands in everything but also because that is where I think I can make the most impact. That is what excites me. It’s my sweet spot. I fundamentally believe that the way we “do school” is outdated, not aligned with our current economic and social needs, and doesn’t work for most kids. Yes, I don’t even think they work very well for the affluent students in the “good schools.”
So, how do you do this?
Repeat Clients: Some people come back for more.
Six years in, the vast majority of my work is now repeat clients. I just wrote the charter renewal for the very first school I helped to design.
Networking: I spend probably 3–4 hours per month (sometimes more) networking.
I belong to the Yellow Hat’s League with Transcend Education.
I go to events.
Every time I talk to someone, I ask them to connect me with 2–3 more people.
When I moved back to Boston permanently, I started all over, and reached out to people to see who was doing ed reform in Boston. They then connected me with other people.
Follow-up: I always follow-up with people about two weeks after a call, to see if they need any help.
Persistence: I’m sometimes a little bit of a pest.
When work gets slow, I send reminder emails to clients saying “Hi, just checking in, I have some time available if you need anything.”
I also work with several organizations that hire consultants regularly, so they are a source of work.
Rhythm of the work: “Feast or Famine”
This work has a rhythm. My busiest months are October, March and July, similar to the school schedule. No one wants to talk to me in late August or early September as they are starting the school year, so I try to take time off then. The same is true around the winter holidays.
It is a little “feast or famine” and I try to take on a lot of work in the winter and spring so I can take time off in the late summer.
My advice on how to start (even if you don’t want to work in education!)
The 4 quadrants:
Make a list of things you like to do
Make a list of things you are really good at
Make a list of things you are bad at, or need to grow at
Make a list of things you hate to do. I also include things here that make you really stressed out. For me, I don’t like evening events. For others, its too many emails. Everyone is different.
The idea here is that you can find work in the crossover sections of things you are good at and like to do. However, you still may need to do the things you don’t like to do, but perhaps less.
What are the top 2–3 priorities for you?
For me, its flexibility and time. (See yoga and traveling below). You would have to pay me a lot of money to give up my flexible schedule!
For others, its’ money. For still others, its benefits, or stability, or professional growth. Consider how much you want to travel for work.
Honestly, I don’t really think that job security actually exists in most places, and that we are increasingly moving towards a gig and project based economy (see: government shutdown), but there are still some jobs that provide more security than others.
Cast a wide net:
Cast a wide net. Consider all the skills from all the jobs you have had, not just teaching. For example, if you worked at a charter school, think of all of the things you have been involved with. Just because you were the Dean of Culture does not mean you can’t coach teachers. Or, just because you didn’t work in HR, doesn’t mean you don’t have hiring skills.
Think of discrete tasks. What are some “one off” things you can do without actually working at the school? What are some temporary tasks? Or tasks that only happen every few years?
What are your translatable skills?
What skills do you use in your job that can be used in many contexts? These are skills such as project management, tech skills, grant writing, hiring, management skills, mentoring, etc.
What are things that people didn’t have time to do or time to do well?
Make a list of things that while working at schools, you or your team didn’t have time to do or didn’t have time to do well. For example, writing charters, writing grants, or reading resumes.
Yeah….but….Isn’t it stressful? Aren’t there tradeoffs?
Ask anyone who works in a high school, especially a charter school, and they will tell you it’s stressful. Many days you are dealing with a crisis or major event — behavior issues, technology failing, taking an entire school camping, etc. So, yes, it’s stressful not knowing where the money will come from. Yes, it can be stressful to handle your health insurance and your retirement. But, I can also go to yoga at 10am on a Tuesday, because I control my own schedule. Or, I went to NY for a few days to stay with my niece when my sister and brother-in-law took my nephew to college. A lot of the time I can work remotely, from anywhere. In the years 2013–2016, I lived in Boston May-October and in San Francisco from November-April. I lived where I wanted based on the season! For me, flexibility and freedom are priceless and are worth any stressors.
Special Thanks to Those Who Helped Me
I am also fortunate to have deep networks, and several friends, family members and colleagues who helped me along the way.
Christina Legg Greenberg, who runs Edgility Consulting, was one of the first people who hired me to help on a project, and continues to be a resource, thought partner, and to connect me with others.
Nate Kellogg, for his constant helpful feedback and for convincing me to write this to “get what is in my head onto paper.”
Naomi Derner, my friend who is a financial consultant who has helped me with legal issues, scope creep, how much to charge, taxes and benefits.
And finally, my sister Kristin Brown Patrick (“KB”) who has been incredibly supportive, a sounding board, reviewed contracts for me, and whom I often hire to help me with any recruiting and selection!
Reach out to Elana to schedule a call. She can share her biggest lessons on:
Logistics: taxes, legal issues, LLCs, insurance, etc.
Money issues: how much to charge, how to manage around “feast or famine”
Scheduling: how much work to take on, how to organize your schedule, how to prioritize
Project planning and what to do about scope creep
Professional development and continuous learning
Generally, what direction to take next
And…. maybe do some introductions and connections!
Elana Feinberg is an independent educational consultant based out of Boston, MA. She works mostly on designing and launching next generation schools to improve outcomes for all students. She can be reached at email@example.com.