Coaching Case Study: Brooklyn Project Manager Looking to Start a Side Hustle

Case Studies

Coaching Case Study By Emma Folkman
(Self(ish) Coach, UNITED STATES)


Six-month coaching contract to help a client achieve their goal of getting a side business started and generating income.

Client Background

The client is a 33-year-old Australian woman living in Brooklyn, New York with a fair amount of debt. She has been working for the same company as a Project Manager for 7 years in order to be able to reside in The United States but she is miserable at her job (and has been for a long time).

She is recently married, which will allow her to apply for a new visa, where she will be able to switch jobs but must wait 6 months in order to receive the updated permit. While she waits for the permit, she wants to start a side business that will bring in extra cash but also allow her to be doing something that she is passionate about.

The client is naturally inclined to self-improvement, always reading books on how to better herself both mentally and physically. She also recently became a certified yoga instructor, which is what ultimately motivated her to start a side business.

Coming to coaching, the client was looking for an accountability coach who could help her make sure progress towards her goal was moving at a steady pace and that she wasn’t letting this passion drop off when life-stressors would inevitably come up.

Explain Process

The client and I met every other week for six months with the goal of getting her side business as a yoga coach set up. Our overarching coaching agreement shifted a few times during the contract; she initially came to me for assistance with remaining accountable to herself in her goal to start up the business but after a few sessions I had observed that there didn’t seem to be a clear vision for the business so we re-contracted to help her flesh out that vision further. We re-contracted a third time when the client came to the realization that she had to put her passion project on the back burner because she needed to be figuring out what it was that she wanted in a new employer when she receives her new working visa and can finally leave the job she has been extremely unhappy in for over 5 years.

Recontracting was a much smoother transition than I had anticipated it to be. Once I made an observation that the client seemed to be having difficulty motivating and staying focused because her idea of the business wasn’t very clear she immediately agreed and outlined a new agreement based on her updated priority.

Core Challenge – Client

Even though the client came to coaching to have accountability starting her business, it became clear to me that she was not fully clear on the vision she was working towards. From week to week, her actions from the previous session would be completed, however, her brain would have pivoted to a different priority that now seemed much more urgent than the path we had left off on.

The client put constraints on her abilities to be motivated and proactive, based on limiting beliefs of how “she has always been”. These constraints limited the progress that she was ultimately able to make because she was unable to open herself up to the idea that what has always been is not set in stone for the future.

Additionally, the client works a fulltime job, prioritizes her health with an in-depth morning routine and yoga practice that limits the time in her day to work on a side project (by the time she gets home from work, she is too exhausted to spend time on her business, which left her with the weekend to dedicate to her passion project).

Core Challenge – Coach

Keeping the client-focused in the sessions was a skill I got to practice in each session. Since we are friends outside of coaching, she would easily get distracted by wanting to tell me about other aspects of her life that were not relevant in the coaching session (more of her venting about frustrations in her life). I learned to not ask “how are things going” at the beginning of our sessions, but instead to immediately jump into “how have you progressed with your work since we last spoke” and focus on accountability on actions from the previous session to cut down on work and relationship venting.

The client also liked to show me her work, as if I was a teacher grading her progress, which I explained was unnecessary but I learned along the way that this was part of her process and I would make sure to allow her space for this but always finding a way to connect it to the current session’s actions or have her relate it to learnings or takeaways she had.

Coaching Skills Leveraged

  • Accountability was what the client came to me to work on and while we broadened the scope once we had worked together for a few months and had a better understanding of what her needs actually were (vs what she had believed they were coming into the coaching relationship) accountability to her progress towards her goal was present in each session. The client created a habit tracker that she could refer to daily to make sure she was staying on track of the main items we determined her focus should be directed towards.
  • Effective feedback was given in each session, but the most important piece of feedback I provided the client within this relationship was that she may need to take a step back and figure out what it was she was really working towards. After a few sessions, I observed that her priorities kept shifting because she didn’t have a clear vision of what it was she was working towards. I sent her a guide on building out a business plan to help her focus on what it was the side business was going to do and how she planned on bringing in extra income. This tool was extremely effective and the client is resigning another six-month contract with me in order to continue to progress on this goal now that she has a clearer picture of what she needs to work towards.
  • Powerful questioning was used to determine the client’s motivators and priorities. I attempted to leverage powerful questioning to help break down the limiting beliefs the was holding herself back with but was unable to get the client to see possibilities past these beliefs she holds firm to.
  • Empathizing with client’s circumstances and their constraints (due to visa situation, current employer, and personal energy levels)
  • Actions were created in each session to keep the client progressing towards her overall goal of having income outside of her 9-5 paycheck.
  • The client was very open to constructive feedback and with the exception of where it related to her limiting beliefs of what she was capable of was extremely receptive.

Results of the Coaching

The coaching resulted in the client being much clearer on her priorities. She also walked away with two extremely beneficial tools.

She had tried using habit trackers previously, but they didn’t fully align with how she works. I encouraged her to be more creative with this idea (and suggested she check out some bullet journal habit trackers online to see the versatility of this concept). She came back the next session extremely excited about her version of a habit tracker that now fits into her morning routine that is extremely sacred to her.

While the client still has not started generating income from her side business, she is building out a business plan to have a crystal clear vision of what it is she actually wants so that she can create a project plan and start making progress towards her goal.

Was the Coaching Effective?

I think the coaching was effective because the client always came to and walked away from the sessions feeling motivated and encouraged. However, there are definitely things that I have learned from this contract that I have already started implementing with my new clients (and this client will now also be participating in when we resign a contract in January).

Changes to Apply in Future

I now have a detailed intake form that helps the client come into the coaching relationship with a clearer understanding of what it is they want and, just as important, where the gaps are. I think this would have helped the client and I identify from the beginning that she wasn’t clear on what the business would look like and how the income would be generated, which “wasted” a few sessions.


The client was my first client that was not a peer coach and was a good introduction to how a “lay-person” will come into a coaching relationship. She always provided a lot of backstories, which of course is unnecessary to the coaching process, but many times it is necessary for the client to process their thoughts out loud. It also gave me practice “cutting off” the client to dig deeper and not have the session turn into pure venting.

While I entered into this relationship wanting to be a “pure coach”, the client helped me see that most real-world clients are unfamiliar with what pure coaching is and, while they may not be looking for a mentor or consultant, they do want input and feedback from you. I tried to keep my feedback to a minimum or would wait till the end of the session when the client had dug deep first for the answers herself before I would give any suggestions or recommendations. I would also send relevant podcasts, books, and exercises to her in-between our sessions which I know she appreciated and also helped keep her on-track and accountable on the weeks we did not have a session scheduled.

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