How First Peak’s Jocelyn Newman Juggles Work, Family, and a Side Business

Side Business Motivation: What inspired you to start a side business alongside your full-time job?

My son was born in November 2020, in the thick of the covid pandemic. Especially during his first year of life, the outdoors became our haven. But the more I adventured with my baby, the more frustrated I became with the baby clothes on the market – it felt like all I could find was cheap, fast-fashion, or products designed to be worn in pristine, indoor spaces. On hikes, my husband and I were wearing highly functional and comfortable performance and athleisure items, and my baby was wearing soggy, stained cotton. 

I was inspired to start First Peak (www.firspeak.co) because I became obsessed with solving this problem. It started more as a project or a mission than a business at all: it grew organically from trying to create better clothes for my own son, to quickly realizing that other families in my community and beyond also shared the same needs.

Career and Business Alignment: How do your full-time career and side business complement each other?

My full-time career focuses on product development and strategy. In short, I’ve spent the past decade helping companies of various sizes to build, launch, and iterate on software products that make users’ lives better. 

My side business complements this work by taking a common skill-set – understanding customer needs, thinking creatively about market opportunities, focusing on delightful design – and applying those skills to the world of garment manufacturing. Working in these fields concurrently allows me to stretch each skill and also view it with a new lens.

Time Management Skills: What are your key strategies for managing time effectively across your career, side business, and family activities?

I’m a diligent note-taker and task manager, and I find that documenting the swirl of to-dos in my head allows me to be more present and focused. I also find that blocking time is critical. Especially now that I work as a consultant, with 2-3 clients at a time on top of my side business, it’s untenable to just jump between focuses. Instead, I split each day into 2-3 chunks (morning, afternoon, and evening), and each chunk should have no more than 1 focus. 

Skill Transfer: Are there skills that you transfer between your full-time job, side business, and managing family activities?

All three of these areas require creative problem solving, patience, and effective goal setting, even more so when juggling them concurrently. I’ve found that this cluster of roles has made me better at each one individually. 

Challenges in Side Business: What unique challenges have you faced in running your side business while working full-time and managing family duties?

I manage First Peak on my own, which introduces unique challenges and opportunities. The work can feel particularly personal, and successes and failures carry more emotional weight than I feel in my full-time job. My side business also feels like a distinct choice to pursue, which can make me feel guilty when it takes time away from family or full-time work. There’s power in the immense autonomy of solo-preneurship, but there’s also pressure and challenge in the full accountability. 

Role of Technology: How does technology aid in managing your career, side business, and family responsibilities?

Since my full-time career has long been in the world of software (including working on Project and Work Management tools like Asana), I actually find it refreshing and focusing to manage my career, business, and family responsibilities in a more analog fashion. I carry a pen-and-paper notebook with me always, and my to-dos are captured in writing. I certainly use GSuite and other work apps with clients, and my online store is run through Shopify, but my management of career, side business, and family happens as much as possible away from screens.

Growth and Scaling: How do you plan for the growth of your side business without compromising your full-time job and family time?

This is an ongoing challenge! Tactically, I lean heavily on the OKR model of goal-setting for my business, setting a finite set of objectives and key results both at an annual scale and then quarterly. This system helps me stay focused on critical priorities and bat off less urgent needs. Also, as mentioned earlier, I aim to proactively block time for each initiative, creating plans on a weekly cadence. 

Professional Development: How do you continue to develop professionally in both your full-time career and your side business?

Networking with other entrepreneurs has been a wonderful source of ongoing professional development. Joining founders networks (e.g. Slack groups, in-person meet-ups) and plugging into non-profits like SFMade have made it easy to connect and share insights and resources. Additionally, I think one of the huge values of my side business is the space is gives me to experiment as a means of professional development – I wanted to learn more about the world of wholesale or marketing, so I set goals to pilot those means of customer acquisition.  

Financial Planning: How do you manage finances for both your career and side business, along with family expenses?

I bootstrapped my side business, and I currently keep all accounting for the business separate from my career and family finances. My husband and I evaluate career-driven income and family expenses together, doing a monthly budgeting exercise managed in spreadsheets.

Success Metrics: How do you define and measure success in your career, side business, and family life?

I’m not a “resolution” person, but I do love themes and reflections. Generally, my means of defining success, particularly when considering my personal and family life, is thinking about a word or set of words that I’d want to encapsulate a year or time period. In 2023, I really focused on boldness and risk-taking. In 2024, I’m thinking a lot about pushing limits and creating my own definition of “home.” 

For my career and side business, I’m certainly more quantitative. But when it comes to personal and family goals, I appreciate the act of setting an intention or theme, even if it’s not directly measurable in the same way. 

Future Aspirations: What are your future aspirations for your career and side business?

It may sound overly simple, but my top goals are around sustainability and energy. I want to find a sustainable balance across work and family that doesn’t leave me feeling guilty or spread thin. I want to consistently find new clients whose work I find energizing and fresh. I’m at a stage of my career where my aspirations aren’t around that next promotion – instead, I feel focused on finding ways to devote more time to family, feeling energized by the work I’m doing, and making enough to sustain our lifestyle. 

Balancing Act: How do you balance the demands of your career, side business, and family responsibilities?

I define a state of “balance” as one where I feel energized and fulfilled at the end of the day. Balance doesn’t necessarily need to be the same number of hours toward each venture, or a specific schedule. Rather, I try to reflect at the end of each day on how I’m feeling, and consider what changes I’m empowered to make for the next day. Now that my full-time work is consulting-based, I feel I have a lot more autonomy to make changes when I feel out of “balance.” 

Work-Life Integration: How do you integrate your work, side business, and family life in a harmonious way?

My side business and family life feel naturally harmonious. First Peak was inspired by our love of the outdoors, and so much of its growth and ongoing product innovation requires us to continue adventuring and meeting other like-minded families. My full-time job is perhaps less obviously synergistic, beyond its role in fueling me creatively. If my career feels creative and productive, those positive emotions naturally integrate with my side business and family life. When it doesn’t feel that way, I know it’s time to make a change. 

Impact on Family Life: What impact does running a side business have on your family life?

My side business forces me to be more scheduled with my family life. Inherently, as a side business, it can’t just exist during normal working hours. Instead, it eats into early mornings, late evenings, and weekends. To avoid a scenario where it eats too far or makes me feel depleted or torn away from family, I aim to proactively block the time I spend on the business, and make that clear to my husband and son. 

Time for Self-Care: With such a busy schedule, how do you find time for self-care and relaxation?

This is an ongoing challenge, and one I’m continuously working on! Especially with my second baby due in just a few weeks, I’ve felt even more need to create time for self-care. By and large, it comes down to asking for help, saying no, and reflecting on what behaviors are most rejuvenating for me. I know that a cup of coffee before anyone else in the house sets me up to feel grounded and calm each day; I know that exercise and time outdoors are critical. Once I establish a finite set of needs, it feels more manageable to create time for them. 

Family Involvement in Business: Do your family members play any role in your side business?

Officially, no, but practically, of course. First Peak was inspired by adventuring with my son, and I now make clothes intended to help families get outside together. My son is still the base model for every product I release, and he tests every design prior to scaled production. My husband is also a target customer whose feedback is so critical to my design process. 

Learning from Failures: Can you share an experience where you faced failure in your side business or career and how you overcame it?

For nearly all of 2023, my family lived abroad, while I was still managing my US-based business manufacturing clothes. One of the hardest failures I had came in the spring of last year, when I learned of a production error that impacted a large quantity of units. I was far away, and frankly, the most reasonable path forward was simply to keep the units on-hold until I was back in the US to evaluate them personally. This meant that I was understocked for months, and had to turn away enthusiastic shoppers. 

To overcome the failure, I really had to focus on preventing the issue in the future, rather than dwelling on what was already lost. I revamped production checklists and interviewed new manufacturing partners to try to avoid a similar issue. 

Frankly, it’s the same approach I’d hope to leverage in difficult parenting moments and career moments: don’t dwell on what could have been, but set a path to not repeat the same mistake. 

Advice for Aspiring Entrepreneur Parents: What advice would you give to parents who want to start a side business while managing a full-time job and family?

I’d say that it’s OK to start small. For me, I called my business a “project” for the entire first year because that felt safer to dive into than a full-fledged enterprise. I also think that documenting goals is critical; otherwise, it’s far too easy to continuously move the goal-post and feel that you’re falling short.