Chloe Olszewski’s Path from Law Clerk to Attorney: Insights from Modern Family Law’s Mentorship Program

Modern Family Law’s Post-Bar Clerk Mentorship Program is designed to bridge the gap between law school and legal practice, giving new attorneys the guidance, experience, and confidence to step into their roles with skill and purpose. Fort Collins Attorney Chloe Olszewski knows firsthand how impactful this program can be. In this interview with Marketing & Communications Manager Caroline Germano, Chloe reflects on her journey through the program, sharing the lessons she learned, the support she received, and the advice she has for future clerks stepping into the world of family law.

Chloe’s Journey Into Family Law

Caroline Germano: To start, could you share a bit about your background and what led you to pursue a career in family law?

Chloe Olszewski: Absolutely. I grew up in the suburbs of Illinois, about 45 minutes outside of Chicago, so I was raised in a busy environment with a lot going on. When it came time for college, I wanted to experience something a bit different, so I moved farther from home and attended the University of Iowa for undergrad.

While I was there, I began volunteering with a domestic violence awareness program and spent time working in shelters. That experience led me to get involved with CASA, Court Appointed Special Advocates, which connects volunteers with children in the juvenile court system. As a CASA volunteer, I had a caseload of children, including one case involving twin boys. I met with their teachers, therapists, and foster parents, and most importantly, I listened to the boys to understand what they wanted. I then presented their perspective in court as their advocate.

That experience sparked my passion for family law. I had always wanted to be a lawyer — even in kindergarten, I said I wanted to be an attorney — but CASA helped me realize just how meaningful and impactful family law can be. It allows you to advocate for people during some of the most difficult moments in their lives, and I knew that was the kind of work I wanted to do.

Discovering The Post-Bar Clerk Program

Caroline Germano: How did you learn about Modern Family Law’s Post-Bar Clerk Program, and what made you decide to apply?

Chloe Olszewski: After completing my undergraduate studies in Iowa, I chose to attend law school in Mississippi. During my time with CASA, I realized that I had grown up in a bit of a bubble in the suburbs, and I wanted to broaden my perspective and gain more life experience before settling down. Jackson, Mississippi, was a very different environment from where I grew up, and it turned out to be a valuable experience.

While I was in law school, I met my partner, and we eventually decided to move to Colorado. Once I got here, I began searching for family law firms in the area. On LinkedIn, I noticed that Karlee Stoppenhagen, the Managing Partner in Fort Collins, had attended the same law school as I did. I reached out to her on LinkedIn to see if she might be open to meeting for coffee and offering some guidance about the family law field.

While visiting her profile, I noticed a posting for the law clerk position. I was immediately drawn to the mentorship aspect of the program, which really aligned with what I was looking for. I decided to apply, and that is how I ended up here.

Caroline Germano: Was there anything else that influenced your decision to apply to the program or anything in particular that stood out about the company?

Chloe Olszewski: Yes, what appealed to me about the program was the opportunity to build my legal skills in a structured way, especially after moving from Illinois to Mississippi and then to Colorado. That journey made me realize how different laws can be from state to state. While there are federal laws that apply everywhere, family law is very state-specific.

As I was preparing for the bar exam and gearing up to practice law in Colorado, I had some concerns about feeling unprepared. Sure, I could read the statutes and look things up, but doing that in isolation every day can become monotonous and overwhelming. What stood out to me about this program was that it gave me a chance to grow within the specific legal framework of Colorado while also learning the firm’s systems and expectations.

It felt like a true stepping stone between taking the bar and becoming a fully licensed attorney. That kind of support is not something you find at every firm. In other places I have worked, you are often just thrown into the deep end and expected to figure things out on your own. While that works for some, I appreciated that this program takes a more intentional, tiered approach to preparing new attorneys for success.

The Clerkship Experience

Caroline Germano: What was your time like as a law clerk with Modern Family Law?

Chloe Olszewski: It was a truly wonderful experience. From the start, the team, especially Ami, Zoe, and Taylor, was incredibly welcoming, supportive, and fun to work with. Logging onto my computer each day and being greeted by such positive and approachable people made a huge difference, particularly compared to some of my past experiences in law firms.

One of the things that stood out to me was the fact that our firm has a dedicated Learning and Development team. That kind of support is invaluable. I looked forward to connecting with them each day, asking questions, and learning from their experience.

Having Ami, a former judge, as part of the team was especially impactful. It is rare to have access to someone with her background, and as a young attorney, being able to ask her questions and gain insight into the strategic side of practicing law was incredibly beneficial. Her guidance and willingness to help shaped how I think about building a successful legal career.

Caroline Germano: Could you share more about what a typical day in the law clerk role looked like for you?

Chloe Olszewski: Sure! At the beginning of the clerkship, we spent most of our time with our cohort. I was part of the first large group of clerks in the program; there had only been one or two clerks in the previous round, but our group had around 15 people starting at the same time.

Each day, we would log on with Ami, Zoe, and Taylor and be assigned different learning topics. For example, one day we might focus on reviewing the divorce statute, another day the APR statute, or how to complete sworn financial statements. We had instructional videos, followed by time for individual work where we could dive deeper into those subjects.

As we progressed, we began integrating more with our assigned teams. Every team at Modern Family Law has a daily morning meeting, and in Fort Collins, ours was at 9 a.m. I would log in, connect with the team, and hear what everyone had planned for the day.

Throughout the program, we also had one-on-one meetings with managing attorneys and other lawyers in our office. These sessions gave us the opportunity to ask questions, shadow calls, and court appearances, and really start to understand the daily responsibilities of an attorney. Many people have experience as legal assistants or clerks before becoming attorneys, but that often does not show you what the attorney role entails day-to-day. This program helped fill that gap.

In the afternoons, I typically worked on research and drafting projects assigned by attorneys. That hands-on work helped me learn Colorado law in a more practical way, which suited my learning style. I absorb information best by doing, not just reading, so this part of the program was especially helpful.

At the end of the day, we had office hours with attorneys from across the firm, whether they were in Texas, Colorado, California, or Washington. These sessions were open-ended and gave us the chance to ask anything. We often had guided topics tied to our daily learning videos and statutes, but we were also encouraged to ask broader questions. It was a great way to access attorney insight in a supportive space.

Overall, the days were full and well-structured. I appreciated that there was always meaningful work to do. In past experiences, I had logged on to jobs and found myself with nothing to do. That was not the case here; there was constant learning, real tasks, and valuable exposure to the practice of family law.

Standout Learning & Mentorship

Caroline Germano: Were there any specific moments or learning experiences during the program that stood out to you?

Chloe Olszewski: One of the most valuable aspects of the program for me was having the chance to take the first stab at drafting motions. Being trusted to prepare initial drafts gave me a unique opportunity to develop my legal writing skills in a real and meaningful way. What made it especially impactful was being able to see how attorneys would review and revise my work, and getting that direct insight into their thought process was incredibly helpful.

Now, as I draft my motions, I find myself applying the feedback and techniques I learned during those edits. In previous roles, I had mostly done more administrative or surface-level tasks, work that almost anyone could do. But here, the attorneys really gave me the chance to dive into substantive legal work. They would say, “If this were your client, how would you handle it?” That level of trust and responsibility was empowering.

After I submitted my drafts, they would walk me through their suggestions. Sometimes they would say, “This is a strong idea, but I would phrase it this way,” or, “I hadn’t thought of that angle, great point.” Even when something wasn’t quite right for the motion we were working on, they would explain why and suggest using it in a different context later. That kind of thoughtful, constructive feedback is rare.

I do not think many other environments provide the time and space for that level of mentorship. At other firms, things can feel very fast-paced and focused only on billable hours. While we certainly track hours here too, Modern Family Law truly prioritizes developing strong attorneys. The program is designed to set us up for long-term success, and that intentional support made all the difference as I transitioned into practice.

Caroline Germano: Were there any mentors who supported you during your time in the program, and how did they contribute to your growth?

Chloe Olszewski: Yes, I would say Kyra and Alex have been especially influential mentors in my office. Honestly, everyone on the team has been incredibly supportive and willing to let me get hands-on experience, but Kyra stood out because she was just about a year ahead of me in the process. She took the bar in February and started shortly after, exactly the path I ended up taking. Having someone who recently went through the same transition has been incredibly helpful.

Kyra has shared so many practical insights from her first year as an attorney. She is always open about what she learned, what mistakes she made, and how I can avoid them. Whether it is tips on managing my calendar or navigating tricky situations, she is always willing to sit down and talk through things with me. That kind of peer mentorship has made a huge difference.

Alex, on the other hand, brings a wealth of experience from her background as a former district attorney. She has encountered a wide range of cases and always takes the time to answer my questions, whether it is through a quick Slack message or a Zoom call. Her perspective has helped me better understand the nuances of family law from both a litigation and strategy standpoint.

Overall, I have been really fortunate to have such supportive mentors. Kyra and Alex, in particular, have played a big role in helping me grow in my first year.

Transitioning To Practice: Confidence, Responsibility & Milestones

Caroline Germano: How did the program support you in making that shift from clerk to practicing attorney?

Chloe Olszewski: Absolutely, it helped me tremendously. I truly do not think I would be where I am today as an attorney without going through the program. It not only gave me time to learn the specifics of Colorado law, which differ quite a bit from other states, but it also gave me the confidence to ask questions and engage more fully in the learning process.

Coming into the legal profession, and I imagine this applies to many other fields as well, there can be this pressure to act like you already know everything. It is easy to feel like you are the only one who does not have all the answers, which can make asking questions feel intimidating.

But the clerkship program, especially the office hours and the accessibility of the attorneys, created a really supportive environment. As cliché as it sounds, it made me realize there truly are no dumb questions. Even when I was hesitant or unsure, whoever I turned to always made me feel like my question was valid and important.

I remember Ami saying early on, “If you have a question, someone else probably has it too. And if it helps you grow, it’s worth asking.” That mindset completely changed the way I approached learning. I started making lists of questions as I went through the program, and if I could not figure something out after trying on my own, I would bring it to office hours without hesitation.

That consistent support helped build the foundation of confidence I now have as a practicing attorney. Even today, I know I can still turn to others when I need clarity, and that mindset was shaped entirely by the program.

Caroline Germano: What was the biggest change you noticed when moving from a law clerk to a full-time attorney?

Chloe Olszewski: Honestly, the biggest shift was stepping into the role of being the one “in charge,” so to speak. Before becoming an attorney, I had spent about seven years in various support roles, assisting attorneys, completing assigned tasks, and then moving on without much follow-up or responsibility beyond that point.

Transitioning into the attorney role meant I was no longer just executing tasks, I was now the one assigning them, reviewing them, and making the final decisions. That shift in mindset was significant. It required me to take full ownership of the work and think several steps ahead, which was a major adjustment.

What really helped ease that transition was the collaborative nature of our firm and the structure of the clerkship program. While I was not yet licensed during the program, it gave me a chance to operate in an attorney-like capacity. That experience helped me build confidence and begin thinking like an attorney before I officially stepped into the role.

So, moving from a support mindset to a leadership mindset was definitely a challenge, but the environment at Modern Family Law made that shift a lot smoother.

Caroline Germano: What was it like for you to officially become an attorney? I imagine it was a really exciting moment.

Chloe Olszewski: It was surreal, especially because becoming an attorney is something I have wanted since kindergarten. To finally receive the news that I had passed the bar and could officially call myself an attorney was such a powerful moment.

What made it even more special was the outpouring of support I received from the team at Modern Family Law. My phone was flooded with texts, Slack messages, emails, and even LinkedIn messages from people across the firm. I do not think I have ever felt so supported by a workplace in my entire career.

That level of encouragement made the transition into the attorney role even more meaningful. I felt prepared, empowered, and genuinely excited to step into this new chapter. Being able to say, “I am finally the attorney I have always wanted to be,” has been incredibly fulfilling.

Skills & Communication Style

Caroline Germano: Were there any specific skills you picked up during the program that you now use regularly in your work as an attorney?

Chloe Olszewski: One of the biggest takeaways for me was gaining the confidence to ask questions. In this field, you often hear things like, “That will come with experience” or “You will understand that over time.” But when you are in the moment and handling something right now, you may not have that experience yet, so being able to ask questions without hesitation is incredibly important.

The clerkship program helped me build that confidence. It also allowed me to begin finding my voice and style as an attorney. By working closely with different attorneys, I could observe various approaches to drafting and communication, and I started identifying what resonated with me. For the first time, I was not just mimicking someone else’s voice; I was developing my own.

The experience helped shape who I am as an attorney today and gave me the foundation to grow into the kind of legal professional I aspire to be.

Caroline Germano: And having the chance to learn from different attorneys with unique styles must have been so valuable. I imagine it also prompted some reflection on their part, too, like, as you asked questions or observed their approach, maybe it made them pause and think, “Why do I do it that way?” It creates a really collaborative learning environment, where both sides can grow from the exchange.

Chloe Olszewski: Yes, even something as specific as phrasing made a big impact. I had the opportunity to sit in on several phone calls with Karlee, and honestly, the way her mind works is incredible. Observing how she phrases things, how she communicates with clients, compared to how she writes in a motion, was such a valuable learning experience.

It helped me understand how to translate complex legal concepts into clear, approachable language. As attorneys, our job is to interpret the law and then explain it to clients in a way they can understand. Speaking in legal jargon does not help anyone. But in law school, that is all you are taught, legalese, so it becomes your default.

Getting to hear how Karlee breaks things down for clients helped me start developing that skill myself. And it is not something that can really be taught in a textbook or a lecture; it comes from listening and observing in real conversations. Having that access and time to absorb her communication style was incredibly valuable.

Serving Clients With Empathy

Caroline Germano: As an attorney, you often work with clients during some of the most difficult times in their lives. What has that experience been like for you?

Chloe Olszewski: Yes, it is definitely intense, sometimes overwhelming, but also incredibly rewarding. One of the main reasons I chose to pursue family law, and law in general, was to make a meaningful difference in people’s lives. And while I know that corporate attorneys make an impact as well, I was drawn to the more personal, day-to-day side of helping individuals through real-life challenges.

I come from a large family, I am the oldest of five siblings, the 13th of 26 grandchildren, and we just welcomed our 16th great-grandchild. So compassion and empathy have always been central values in my life. When I saw that Modern Family Law shares those same values, it immediately stood out to me and was one of the things that drew me to the firm.

I try to carry those values into every client interaction. Just because someone needs legal help during a difficult time does not mean their attorney has to be intimidating or detached. I believe we can offer strong legal support while still showing care and understanding. Stepping into that role and being a steady, compassionate presence for clients has been one of the most fulfilling parts of this journey.

Culture & Support At MFL

Caroline Germano: Speaking of the firm culture, how would you describe the environment and the support system at Modern Family Law?

Chloe Olszewski: I would describe the culture at Modern Family Law as incredibly welcoming and genuinely collaborative. Initially, I had some hesitation about joining a firm that operates primarily in a virtual or hybrid model. I was concerned that I might not be able to build the same kind of strong relationships with colleagues that I had at more traditional, in-person firms.

But those concerns quickly faded. In fact, I now feel more connected to my colleagues, both across the country and within my local team, than I ever have in past roles. The structure of our daily morning meetings, regular communication through Slack, and the ease of jumping on Zoom calls really fosters connection and support.

What stands out most is how intentional the firm is about cultivating a sense of community. It truly does not feel like a traditional law firm, we are friends, we work well together, and we genuinely want to see each other succeed. Channels like our “Master Channel,” where team members celebrate wins and recognize each other’s efforts, are just one example of how uplifting and encouraging the environment is.

The people here, our attorneys, support staff, and leadership, are outstanding. And beyond the professional excellence, what sets this firm apart is how much it values its people. We are not just seen as numbers or billable hours; we are treated as individuals. That culture of care and support is a big part of why I joined MFL, and more importantly, why I plan to stay. I feel seen, appreciated, and empowered here, which is something I have not experienced at other firms.

Advice For Future Clerks

Caroline Germano: Are there any pieces of advice you would offer to new clerks going through the program?

Chloe Olszewski: My biggest piece of advice would be to soak in as much as you can. Take advantage of every opportunity, ask questions, attend hearings, and shadow anything and everything, even if it feels too advanced or too basic. There is something to learn in every experience.

The clerkship program is a unique and valuable time to get yourself organized and prepare for the next step. Use it to figure out what works best for you, whether that is how you manage your calendar, set up your workspace at home, or develop your personal workflow. At many firms, you are immediately thrown into the deep end, but here, you are given the space to ease in and build a strong foundation.

Be proactive. Join Zoom calls, observe how others operate, and make it a priority to connect with people. Building those relationships during the program is so important. Your fellow clerks are going through the same milestones: your first court appearances, your first clients, your first ICIs, and having a support system of people who understand what you are experiencing makes a huge difference.

Take full advantage of the program. It is the perfect time to grow, explore, and prepare for the kind of attorney you want to become.

Looking Back

Caroline Germano: Looking back on your experience so far, what are you most proud of in your role as an attorney?

Chloe Olszewski: Right now, I would say I am most proud of the personal and professional growth I have experienced. When I look at where I was just two months ago compared to where I am today, the difference feels like night and day. I truly do not think I would have reached this level of confidence and capability as an attorney without the support of both the clerkship program and Modern Family Law as a whole.

I have never felt so consistently supported in a professional setting. The check-ins, encouragement, and overall care from the team are unlike anything I have experienced at other firms. Even small, unexpected moments, like Clem from the Sales team reaching out with a thoughtful message, can completely brighten my day. Her positivity and kindness genuinely make me feel seen and valued.

That kind of culture makes a huge difference. I am incredibly proud of how far I have come, and I credit so much of that growth to the environment at Modern Family Law and the people who have supported me every step of the way.

Conclusion

From hands-on drafting and daily mentorship to a supportive culture that encourages questions, Chloe Olszewski’s journey shows how a structured post-bar program can accelerate growth and confidence in family law practice — turning new graduates into client-ready advocates.