How I Started My Coaching Business

College Beginnings

During my junior year at Brown, my roommate Anastasia volunteered the career coaching center.  It was located in a gothic building on the edge of campus.  I saw her reviewing resumes one day, and was like, "wow that looks cool," mostly because I was curious about other people's resumes.  She told me they were looking for more student volunteers.  After a few intensive training sessions, I became a Peer Career Counselor and once a week I would set up shop at the center and take walk-ins for my four-hour shift.  I learned how to write a resume, cover letter, and started helping with interview prep workshops.  I never thought I would become a career coach, it was just something I did on the side, like writing for the Brown Daily Herald or being a cheerleader.

My First Website

Fast forward about ten years later, I had just moved from Denver to New York City and I had an infant and a toddler.  I was still recovering from corporate burnout, was surrounded in a rented townhouse with floor-to-ceiling cardboard boxes, and I was overwhelmed.  I was going to stay home with the kids at least until we got settled, so in the meantime I wanted to make some cash.  I set up a simple website, picked a name (Rose Gold Careers) and went to work.  At first, all I did was have a resume package, LinkedIn package, and interview prep package.  My resumes back in the day started at $200.  I really wasn't thinking ahead.  I was just thinking, "maybe if I sell a couple of these then it will help me pay the bills a bit."  That's all.

I made a post on LinkedIn that basically said, "hey I'm starting a side hustle doing people's resumes, let me know if you need help with yours."  That night, one of my former classmates reached out, and I was in business.  I also joined a local moms group on Facebook and made a post about my services there.  That's it.  Within a week, I had three clients.  That's how I started my business.  I didn't go around talking about it, I was pretty much just motivated by making a buck here or there.  Sometimes at my kid's gymnastics class I'd meet another mom and they'd ask me what I do, and I'd tell them: oh I help people with their resumes from time to time.  I did a ton of free resumes, too.  If anyone I personally knew needed help, it just seemed like a duty.  Like, this is a random skill that I have, of course I will help you.

Growth Was Slow and Boring

There was never a moment when my business exploded.  It really didn't.  It was super slow growth, and grew entirely word of mouth.  I'd do someone's resume, they'd like it, and then they'd be like, "hey can you help my sister," or "my best friend actually needs help" or "my husband might be looking for a new job soon."  One of the nicest things about it was that people that I hadn't talked to in ages -- literally from middle school or college -- would come out of the wood work.  "I don't know if you remember me..."  OF COURSE I REMEMBER YOU.  It was all these little sparks, all these little connections.

As it grew, I used to freak out about it not being big enough.  I felt I had more in common with a cobbler, shining one pair of shoes for their client at a time.  Why wasn't I out there raising millions of dollars for a resume-based startup?  Shouldn't I be doing something more?  "Well," one of my consulting friends told me one time, "there is a ceiling right, on how much you can make -- just based on your time?"  I felt bad about not figuring it out, and having this silly little lifestyle business.

Not Feeling Enough

One time I was on a family vacation in Japan, and it was over the Christmas break.  Of course this is also the time when lots of people are in need of resume help.  I got three or four emails asking for my availability, would I be able to help them?  They got my autoresponder, and then I emailed them back as well to let them know, I'm sorry, I'm traveling, I can't help you right now.  I remember feeling torn up about that.  Partly I was frustrated because I was losing out on sales.  Partly I was annoyed to be bothered on vacation.  

Why can't I crack it?  Why can't I crack it, I always wondered.  It seemed like everyone else had these super flexible businesses where they didn't have to work as hard as I did.  I was literally inside people's resumes: looking at every bullet point, moving around semi-colons, arranging keywords like a composer.  Every detail mattered.  The work product was excellent.  But resumes are a lot of work.

Trying to Scale LOL

I tried hiring people -- who were mostly excellent -- to serve as resume writers and as a point of contact for the clients.  This is called scaling by growing an organization.  In some ways, I was able to be the face of the brand, and sell.  But then I was just the administrator: following up with my contractors to make sure they got the resumes done in time, and then emailing back and forth with the clients to make sure they were happy.  I wasn't ever sure they were happy.  They probably were, but I felt disconnected from the business and generally exhausted.  I might as well have been running a refrigerator coolant company; there wasn't any heart to it to be honest.

Over time, I should mention, the resume work took a turn into coaching work, which is a natural progression.  If you're in the coaching world, you should probably expect this.  They dovetail nicely together.  I think the resume stuff is like the gateway drug; it's transactional, people want it, it's very cut and dry.  But then of course, it's just a fancy piece of paper.  How do you figure out what you really want to do in life?  What do you do with all of these big feelings around leaving your job, pivoting, doing something riskier?  

Coaching and Getting the Reps In

I was a coach full-time for about four years.  Day in, day out, that's all I did.  I had about three or four sessions a day.  My days were packed.  I wasn't great at it at first, but I stuck with the discomfort and moved past the feeling of wanting to "fix" everything - and realized that instead of fixing, most people just want to be heard and understood.  I felt like my job was to be honest in the sessions.  I don't mind saying the things that need to be said.  The goal was that by hearing someone be honest, it's permission for the client to be honest with themselves as well.  And the more they can tolerate (and eventually promote) their own honesty, the better decisions they will make.

So you start to see people making brave decisions, like leaving jobs, starting businesses, standing up to bosses, having difficult conversations - even staying at jobs because they've come to peace with themselves and don't need to fight everything all the time.  

Building my Social Presence

In 2022, I started posting on TikTok.  Basically, I took the conversations that I would have in my coaching sessions and turned those into simple Q&A videos.  People would comment things like, "omg how do you know this, you're inside my mind," and the truth is if you do enough coaching sessions, you get good at spotting the universal themes and everyone is pretty much having the same feelings of imposter syndrome, needing external validation, not feeling motivated, etc.  I think my gift is the ability to listen to people and then draw some sort of nice, hopeful conclusion that might otherwise go unseen.  Seeing in the dark and all that.  And my extra gift is that I am a hard worker and delay gratification which is what's needed when you create content.  Where most people gave up, I just kept going, and that's how I built my platform.