Trapped in middle management

I have been working since I was 16 years old. I've always had a job. Through high school and college, I worked. I graduated from college magna cum laude. After college, I worked. Full time, and often with a side hustle. I've never been without work.

"You want a car, honey?" my dad asked
"YES!" I replied enthusiastically
"Then you want a job." 

This sums it all up. If I've ever wanted something, I've had to work for it.  Lucky for me, though my parents wanted to teach me the value of hard work and never wanted to spoil me, they’ve ALWAYS had my back if I’ve needed them. This is a privilege I readily acknowledge and don’t take for granted.

You might think that this long job history means I've reached great career heights and am no longer living paycheck to paycheck (I'm 35), or that my 401(k) is overflowing: you're wrong. Like many people my age, I switched careers often, but I found myself (stupidly) making lateral moves to similar sized organizations. Furthermore, the organizations and businesses I worked for offered little room for growth. Or, once I got promoted, I was made to feel lucky to have a job "in this economy." Or, I was hired in at the top for a low salary because of my terrible negotiation skills and straight up inferiority complex. I've never got more than a 5% raise at one time, despite being a top performer and, quite frankly, always working my ass off. I am trapped in middle management. This apparently happens to a lot of women, in every sector. 

First, I picked an industry out of one part passion and one part complete naivety: the nonprofit sector. I’m sure people told me that this wasn’t a lucrative industry, and I’m even more sure I didn’t listen. Second, within that sector, I've worked for arts and environmental organizations; not exactly institutions like  universities or hospitals (also nonprofits). Third, I've made some big mistakes when asking for a raise (more on that later) and generally when communicating with Director-level staff. Fourth, I am a woman who is small in stature and looks younger than I am, something I am happy about 100% of the time out of the workplace, but that has proven time and again to be a disadvantage. I know I'm underestimated and undervalued before I have the chance to open my mouth.

2018 is the year I am going to get unstuck. I need to, out of necessity and out of pure frustration. I just got married, and my husband and I are thinking about buying a house. Real talk: in Los Angeles, a 2 bedroom, 1 bathroom house built in 1925 in an "up and coming" (ie, gentrifying) neighborhood costs a cool $850,000. I can't even begin to afford that. And frankly, my heart sinks and I feel real, deep insecurity and inferiority when I see starting salaries at big companies requiring no work experience at more than I make now. A lot more. 

The thing that makes this especially hard is that, generally speaking, I love my life's work. I like working for nonprofits, in service of missions and visions that align with my own values. That's extremely important to me, and for a long time, I paid myself on the feeling of goodwill that these jobs have given me. But it was easier to scrape by when I was just concerned about myself. I still don’t really concern myself with what others think of me – that’s a fool’s errand, and if I’ve learned anything over the course of my life it’s that comparison is the thief of joy. But now that I want a house, and maybe a kid or two, I have to start thinking about that, and I can’t get by on good vibes and a pat on the back for a job well done.

I literally have no idea where I need to start, but I have a bunch of educated guesses, and I am going to do them. If they don't work, I will stop doing them, and move on to the next thing. Here's my plan for making what I am worth. 

  1. Find a mentor. This is touted as a must-do in all my favorite podcasts like Women, Work and Worth by Mavenly. I might even dig deep in my very shallow pockets and hire a career coach.

  2. Work on my etiquette and wardrobe. This is a tough one for me. I've ONLY worked in casual office environments. Currently, I work from home 3 days a week and have to give myself a pep talk to put on pants on those days. I have the mouth of a sailor and my clothes are second hand. Changing both of those things will make a big difference in how I am perceived. 

  3. Join Toastmasters and learn to tell a really good story without saying “ummmm”or “like” even one time. 

  4. Develop my personal pitch, and variations based on whom I'm talking to and practice. 

  5. Join a non-cheesy, non-meat-market-y, useful networking group.

  6. Remain aware of my strengths, and use them to my advantage as often as possible. My top five are: input, positivity, achiever, adaptability and relator.

  7. Write down my goals and look at them and work towards them every. damn. day. 

  8. Ask successful friends to review my resume and re-work as necessary. 

  9. Get up earlier and stop rushing. 

  10. Listen to those who know more than I do. 

  11. Keep doing the things I love, like yoga, rock climbing and hiking. Healthy body, healthy mind – right?

  12. Read more books on professional development and self-improvement and consume more podcasts. I’ve already read How to Win Friends and Influence People by Dale CarnegieDaring Greatly by Brene BrownYes Pleaseby Amy Poehler, Difficult Conversations by Doug Stone, The Four Hour Workweek by Tim Ferriss. Current (career-related) podcast favorites include Two Inboxes, the aforementioned Women, Work and WorthBeing Boss, and Heroine. Any other suggestions?