I narrowed my eyes at his tenth excuse on why he didn’t apply to any of the curated remote job leads in the list that I sent him. I told him that one, in particular, was perfect for him.

The homeless client narrowed his gaze in return, his head cocked as if ready to call me Miss Thing again.

In resistance, I knew that he was battling fears of success and insecurity which led him to act out. It’s not uncommon with career clients, homed or not.

Working with a homeless LGBTQ drop-in center for two years, I dealt with challenging and heartbreaking cases every day. I have helped homeless transgender people of color find work in a conservative state. Even with my current contracts with tech bootcamps, I am often called in for tough cases. It’s why I am so confident when working with UX Designers and tech professionals. They got problems, but they don’t have ‘black transwoman with just a GED in Arizona’ problems.

I was helping a man, recently out of recovery and with a college education, find a remote job in the travel industry. It was a tough mission because first I had to coordinate with his housing case manager to get him into housing, then I helped facilitate a referral to therapy, and I managed to source a serviceable desktop computer. Then, of course, he had a very specific job request.

It’s good that I like a challenge!

Back to my story, the stare off continued as I repeated that he needed to apply to these remote jobs once he saw them open. Remote jobs close frequently. He had excellent writing skills, could interview well and had gotten all that he needed to work remotely… He just needed to apply.

He started shaking his finger in my face and raising his voice, his pale face getting red.

“I won’t be yelled at. Schedule me next only after you have applied to these jobs.” I stood up, put my bag on my shoulder, and walked away from the makeshift table in the cramped and underfunded drop-in center kitchen which functioned as my office. I had done the coddling, now I had to be firm.

Boundaries could always be a risk with clients.

Our drop-in center had a good culture, but we have had to call emergency mental health professionals, deal with staff having their tires slashed, and physical threats more than once. Somehow I never had a client try to take a swing at me in my two years of being there.

I have been called one of the motivating and kindly coaches in every place that I have worked. Interestingly, I have also been seen as the toughest by some tech bootcamp students.

Don’t get it twisted about my professionalism: I am polite, but firm when needed.

It doesn’t do a client any good if I approve a portfolio that isn’t professional grade. If I don’t encourage my clients to find their style with networking and actually do it, then I am doing you a disservice. Letting someone stay in their stagnant comfort zone might make them like me more, but it’s not going to give them their ROI.

This is the truth: staying in resistance, leaning into fear, and refusing to take feedback is how you end up in a rut. That is how your life and career stays stagnant. It feels comfortable because it’s the cage that you are used too, not because you like being there. It’s easy to forget that when you are putting yourself out there for your goals and dreams

I will do everything I can to help a client succeed. That includes a loving metaphorical kick in the pants.

Maybe some coaches are fine with their clients staying in the same place month after month, year after year, but I am not. I want you to not need me.

I want to see my clients build up their grit, learn important life skills, and achieve their goals.

If that means that I have to push you into accountability… well, that is why you paid me.

Your friends won’t hold you to your goals.

Your family won’t keep track of your dreams.

Your partner won’t ask the hard questions about your accountability tasks for the week.

They don’t want to make the waves that you need to learn how to swim.

A good career coach will and I have worked with harder cases than you, honey.

My homeless client avoided me for a week.

Lord knows that I needed a break from him too. My mentor at the center told me that I needed to detach myself more or else I would burn out. They were right, but I have always had a hard time not investing myself in my client’s goals.

The week passed and my challenging client came up to me with his hand out to shake mine. He told me that he had applied for the job. I shook his hand and told him that I had a good feeling about the job.

He eventually did get that remote job, customer service in the rental car business. Last I heard, he had reconnected with his family before moving back to his hometown.

This story had a happy ending because both my client and I worked for it by pushing through to achieve a goal.

Are you going to work through the discomfort, the fear, and the insecurity to get your happy ending?

Just saying… Why be miserable for 40+ hours a week? Kickstart your career; kickstart your life!