10 Tips for Pivoting into a Career That Advances Liberty

Nothing makes me happier than hearing from someone who wants to move into a career that advances the principles of economic freedom, free enterprise, and limited government.

I made that transition myself many moons ago and it was one of the best decisions I’ve ever made (along with rescuing a dog and not going to law school…no offense to cat lovers and lawyers).

But making the transition wasn’t easy for me because of a few misconceptions that I had.

With that in mind, here are the 10 things I wish I knew back then, as it would have made the transition a lot easier.

1. The free-market nonprofit sector is not a talent wasteland. There is a misconception that the nonprofit sector is desperate for talent, and that when we find someone with strong private sector experience, we trip over ourselves to hire the person. This isn’t quite how it works. The free-market universe is filled with amazingly talented and smart people. Now, to be sure, we’re always looking for more people to join the fun! But most of the searches we work on have stiff competition; so, put your game face on and be ready to compete!

2. You may need to adjust your salary expectations. I took a pay cut to come into the free-market universe because I valued fulfillment and advancing change more than I valued the additional income. Had I not been flexible on the salary front, I’d probably still be searching for a liberty-oriented job!
Especially if you’re well into a lucrative career in, say, big law, corporate lobbying, or even the federal government, chances are slim and none that you’ll find a job in the free-market nonprofit world at your current salary (and Slim just left town). (Speaking of, do not go into a nonprofit interview process and reference your GS pay scale! “Um, yeah, I’m a GS-15” will likely be greeted with confusion, eye rolls, or both!)

On the bright side, salaries aren’t stagnant. You might have to take a financial step back when you make the transition, but you can make up for lost ground over time. In fact, you can make a fine living in the free-market space! White-shoe firm money? Nope. But you won’t have to work 120 hours a week, bill your time in six-minute increments, and I suspect you’ll actually like your job.

3. A lateral move may not be possible. Unless your skills translate perfectly for a role in the free-market nonprofit space, you may need to take a less senior role in which you can learn the ropes and gain an expertise relevant to the nonprofit space. If you are unwilling to do this, you may find making the transition very challenging.

4. Apply for jobs for which your skills and experience are a strong match. Changing sectors is hard enough, but trying to change sectors and land a completely different type of job is REALLY tough. For instance, if your background is in sales, it’s going to be incredibly difficult to land a policy analyst position in the liberty movement. But an entry level fundraising or marketing role might be more accessible. If your background is in private sector project management, it’s going to be an uphill battle to secure a communications role with a free-market nonprofit. However, an operations job might be within reach. Aim for jobs that require the skillset you already have; not the skillset you hope to one day develop. (Pro tip: READ the job description. If your skills and experience don’t line up at all, it’s best to keep looking!)

5. It may not happen overnight. Don’t give up. Shortly after Talent Market launched in 2009, I got connected to a very talented businessman who wanted to pivot into the free-market movement. We explored multiple opportunities together, and I’m happy to say Talent Market eventually helped place him in a great role…seven years later. Yep. Seven years. I wish it hadn’t taken that long, but finding the right opportunity wasn’t easy for someone with his unique background — just like it wasn’t easy for me, and it may not be for you. Now, to be clear, I don’t necessarily think it will take you seven years, but you probably won’t land the first liberty-advancing job for which you apply. Be patient and keep trying!

6. Think twice before getting that graduate degree. If you’re planning to get a graduate degree in order to help you transition into the liberty movement, slow your roll. I did that and ended up with a diploma that catches dust and an education I don’t use. Moreover, I scared potential employers who didn’t want to pay a premium for an advanced degree that wasn’t going to be useful for the job they had open. Make sure an advanced degree is necessary before going that route. When in doubt, opt for experience over education.

7. Show us you are passionate about liberty. Those of us in the liberty movement are passionate about what we do, and we want to hire people who share that passion. So, a job applicant who has zero demonstrated interest in advancing liberty may not get traction with the hiring manager — especially if the candidate is competing with other candidates who have proven they care about the cause.
If you haven’t previously worked in the liberty movement, make sure your application package includes everything you have done that speaks to your interest in liberty. Are you a member of America’s Future or Federalist Society? Did you attend an Institute for Humane Studies seminar? Were you active with Young America’s Foundation or Students for Liberty in college? Are you active with other liberty-oriented organizations or causes? Did you intern in the liberty movement a decade ago? Put it on your resume! Never been formally active in the liberty world but grew up reading Hayek and protesting teachers unions? Tell us in your cover letter! Speaking of cover letters…

8. Tell us you are passionate about liberty. In addition to a resume that illustrates your interest in liberty, be sure your cover letter makes a compelling case for your interest in making a move into the free-market nonprofit sector (and, of course, the job for which you are applying).

I cannot tell you how many candidates we see who attempt to make the transition into the liberty movement using generic cover letters that could easily be used for a customer service associate opening at TJ Maxx. Not once in my career have I seen a candidate with a generic cover letter land a job in the liberty movement.
If you’re having trouble “breaking in”, go back and review the cover letters you have written. Were they compelling? Did they clearly articulate why you want to be a part of advancing each organization’s mission? Or were you just phoning it in with “Get the max for the minimum” cover letters? If you really care about making the leap, put your heart and soul into the cover letter.

9. The longer you wait to make the transition, the more challenging it will be. If you spend a few years in another career and then pivot toward the free-market movement, you can probably make that change happen. But if you spend 20 or 30 years in another career, the transition could be very difficult.

Once you have been working for 20-30 years,  not only will you have developed a skill set that may not align with the nonprofit space, you’ll also likely be trapped in the golden handcuffs and command a higher salary than nonprofits are unable to afford. Regardless of timing, you can still make the transition; you just might have to be more flexible and open-minded about salary, geography, level of role, etc.

10. Own your pivot. You are attempting to transition to a new sector, one that is likely very different from your previous work. Neglecting to mention this in your application might underscore to the hiring manager that you aren’t really passionate about making the change or that you don’t understand how different this world might be. So, OWN IT! Acknowledge in your cover letter that you want to make a big transition and explain why (see #7 and #8). Help the hiring manager understand how your skills and experience translate to the job for which you are applying; do not assume that they know the acronyms and jargon used in your previous lines of work.  Finally, acknowledge that you have a lot to learn and tell them how excited you are to do so.