On Strategy Showcase: Life after Agency Life Ep#3

Release Date: April 27, 2025
Host: Fergus O’Carroll
Guests: Tom Morton, Britton Taylor, Lisa Prince
Series: Planning on the Outside

Introduction and Context

In the third episode of the “Planning on the Outside” series, hosted by Fergus O’Carroll, the focus shifts to exploring the journeys of strategists who have transitioned from traditional agency environments to independent ventures. Joined by former agency professionals Tom Morton, Britton Taylor, and Lisa Prince, Fergus delves into their motivations, challenges, and insights gained from life beyond the agency walls.

Guest Introductions and Backgrounds

Tom Morton
Formerly the Chief Strategy Officer at RGA, Tom is the founder of Narratory Capital, a strategy consultancy aimed at helping creative businesses and brand owners build sustainable futures. He shared his transition journey, highlighting his shift from agency executive to entrepreneur.

Britton Taylor
Britton’s path began unexpectedly after an English major and a stint teaching seventh grade. Inspired by John Steele’s book on strategy, he transitioned into advertising, spending 16 years at Wieden+Kennedy in San Francisco before embarking on a freelance career. Britton now runs Tritton Baylor Strategic Industries from Portland, Oregon.

Lisa Prince
With 25 years of experience as a creative strategist, Lisa moved from the UK’s Euro RSCG and Wieden+Kennedy London to the US, where she served five years at Wieden+Kennedy Portland. Feeling constrained by the agency environment and seeking better work-life balance, Lisa founded School of Ideas, a company dedicated to teaching innovative thinking and creative problem-solving.

Transition from Agency Life to Freelancing

Motivations for Change

The guests shared varied motivations for leaving agency life:

• Lisa Prince emphasized the need for better work-life balance, especially with young children, and a desire to tackle bigger, more meaningful problems beyond the constraints of agency specialization. She noted, “I wanted to think a bit bigger… solve big tricky problems for clients” (08:33).

• Britton Taylor spoke about reaching a "glass ceiling" in agency roles and yearning for more autonomy and creative freedom. He mentioned, “It was not inspiring to me… I have much more freedom working for myself” (25:18).

• Tom Morton highlighted a similar desire for autonomy and the opportunity to focus deeply on strategic challenges without the administrative burdens of agency life. He reflected, “the ability to create collectives and tap into and hire like-minded experts is going to be really important” (43:46).

Challenges Faced

Transitioning from agency to freelance wasn’t without its hurdles. The speakers discussed learning the business side of strategy, such as billing, client acquisition, and defining their unique value propositions.

Benefits and Challenges of Freelancing

Advantages of Independence

• Autonomy and Flexibility: Freed from rigid agency structures, the guests could tailor their work schedules and choose projects aligned with their passions. Lisa shared, “I built a lifestyle business… take two months off every summer” (26:56).

• Creative Freedom: Freed from agency constraints, they could engage in more meaningful and innovative projects. Britton noted, “I can pick and choose the people that I want to work with… solve those sorts of big strategic challenges” (15:07).

• Personal Growth: Engaging in activities beyond advertising, such as volunteering and continuous learning, enriched their professional and personal lives. Britton added, “Being a freelancer has afforded me the privilege to honestly devote a lot of my time to doing things that aren't advertising or marketing related” (30:15).

Challenges Encountered

• Business Acumen: Transitioning strategists needed to develop strong business skills to manage billing, client relationships, and project scoping. Lisa emphasized the importance of this, stating, “How much you should charge, where your value is, how you scope a project… really important” (52:35).

• Client Acquisition: Building a steady stream of clients required proactive networking and continuous relationship cultivation. Britton mentioned, “Opportunities keep bubbling up… But you're right, the grind is real” (35:51).

• Managing Peaks and Valleys: Freelancers often face fluctuating workloads, necessitating strategies to maintain a balanced workflow. Fergus shared his own experience: “You come off of projects almost terrified where the next one is going to come from” (33:08).

Building and Maintaining a Freelance Business

Strategies for Success

• Networking and Partnerships: Forming alliances with other professionals was crucial for managing larger projects and diversifying expertise. Britton highlighted his partnership with Katie Drakey, enabling them to tackle global strategy projects together.

• Value Proposition: Clearly defining what sets their services apart helped in attracting the right clients. Tom explained, “You need a very clear understanding of your own value proposition and what you're the right person for” (49:51).

• Continuous Learning and Adaptation: Engaging with different learning platforms and communities, such as Slack groups and freelance guilds, provided ongoing support and opportunities.

Maintaining Work-Life Balance

Fostering a healthy balance was a significant focus, with strategies like taking regular breaks and aligning work with personal strengths and preferences. Lisa shared her system of deep work in the mornings and administrative tasks in the afternoons, complemented by scheduled summers off to recharge.

Advice for Aspiring Freelancers

Essential Preparations

• Develop Business Skills: Gain proficiency in billing, client management, and defining clear project scopes. Lisa advised, “Spend as much time as you can in this year learning that bit of the business” (52:35).

• Build a Strong Network: Cultivate relationships within the industry to generate referrals and collaborative opportunities. Britton recommended being part of multiple Slack groups and creating a supportive community.

• Define Your Niche: Specializing in a particular area of strategy can make you more attractive to clients seeking specific expertise. Tom suggested choosing a “swim lane” that aligns with your strengths and market needs (21:39).

Overcoming Fear and Uncertainty

The guests acknowledged the inherent anxiety in leaving a stable agency position but emphasized the long-term benefits of independence. Tom encapsulated this sentiment: “Anxiety is the price you pay for freedom… it's worth it” (54:43).

Conclusion

The episode provided a comprehensive exploration of the transition from agency life to freelancing. Tom Morton, Britton Taylor, and Lisa Prince shared their personal journeys, highlighting both the rewards and challenges of independent strategy work. Their collective wisdom offers valuable insights for strategists contemplating a similar move, emphasizing the importance of business acumen, networking, and maintaining a healthy work-life balance. As Fergus O’Carroll aptly concluded, the freedom and fulfillment derived from freelancing make the inherent challenges worthwhile.

Notable Quotes:

• Tom Morton (43:46): “I think that ability to create collectives and tap into and hire like-minded experts is going to be really important. So yeah, I think that for a while the future is going to belong to these like amorphous, like-minded bands of people.”

• Lisa Prince (26:56): “We take two months off every summer. And I will tell you this, what I've realized is your USP becomes the fact that you're rested…”

• Britton Taylor (15:07): “I feel like I'm feeling much more freedom working for myself. I can pick and choose the people that I want to work with…”

• Fergus O’Carroll (55:54): “Lisa Prince, founder of School of Ideas and Mrs. Prince, LLC before her consulting work. Britton Taylor is freelance strategist in Portland, Oregon. And Tom Morton, Narratory Capital is his firm in New York City.”

This episode serves as an insightful guide for strategists considering leaving the agency scene, offering practical advice and inspiring stories of successful transitions.