Jenna Spencer on building a company that gives her time back.

Spencer had three children and was unhappy with the amount of time her corporate schedule kept her away from them. She began working from home as an executive assistant to two business coaches. About six months later, they pointed out a need for capable assistants in their industry and encouraged her to consider building something around it.

Friends were also asking what she was doing and how they might find similar work. Spencer recalls telling her husband that she felt compelled to try because she could help other people work from home.

The appeal included both family life and professional satisfaction. She wanted control over her schedule, but she also valued work and professional conversation. AssistPro, which she says she started in 2014, grew from trying to make those needs compatible for other people as well as herself.

Spencer describes her early reactions to problems as much more intense than they became with experience. Each setback could feel as if it threatened the whole company. Over time, having worked through earlier difficulties helped her respond more calmly.

One early mistake involved billing. The company owed clients time and hours, creating an obligation she describes as five figures. At that stage of the business, the size of the error felt overwhelming.

Her father-in-law, an important mentor, told her that a problem that took time to develop would take time to work through. His advice was to create a process and follow it step by step. Spencer returns to that lesson more than once in the interview. It helped her replace the pressure to fix everything immediately with a practical sequence of actions.

Spencer once felt that she had to take every opportunity quickly or lose it. A later realization was that opportunities would continue to exist, while her own ability to lead needed to develop alongside the company.

Reaching a larger revenue level did not automatically make the work easier. It introduced different problems and required another stage of personal growth. Accepting that pattern helped her settle into the role instead of interpreting new difficulty as evidence that growth had failed.

Her story is useful for founders who keep moving the point at which they expect the business to become simple. Spencer found more stability by expecting to learn at each stage and choosing her next opportunity with more patience.

During the pandemic, Spencer decided to put money back into AssistPro despite substantial uncertainty. She describes it as one of her scariest decisions and says it ultimately benefited the company. She does not provide a detailed investment breakdown or suggest that every founder should make the same choice.

What she explains is how she approached the decision. Mentors asked what she wanted, what the pros and cons were, and what she believed she could handle. They did not give her the direct answer she initially wanted.

By then, Spencer had more confidence in her ability to build. She believed that if things went badly, she could start again. That belief did not remove the risk; it changed how she viewed her capacity to respond to it. She also credits Strategic Coach and the idea that clarity creates confidence with helping her understand her goals more precisely.

Spencer uses the term visionary from the Entrepreneurial Operating System, or EOS, to describe the work that suits her. She enjoys ideas, leading people, speaking, and networking. Earlier, she had assumed that being an owner meant personally managing detailed checklists and organizational tasks.

Those operational tasks still needed to happen. She hired an operations director whom she describes as the glue holding the team together, and she worked with an assistant who understood how to help her communicate effectively.

That support changed the way information moved from Spencer to her team. She could record a video or talk through a topic rather than forcing every contribution into a written report. The assistant helped translate that communication into what the team needed. The change was more specific than simply delegating: she developed a working arrangement that let different people contribute in ways they could sustain.

When Spencer mentors someone else, she first tries to understand how that person communicates. Some people work through ideas by writing, others by talking or listening. She then connects the discussion to the person’s goals and asks them to imagine what achieving those goals would involve.

She also pays attention to energy: which situations excite the person, which drain them, and which urgent problems are consuming their attention. The aim is to help them lead themselves rather than provide a standard answer.

The same attention to fit appears in hiring. Spencer describes carefully defining a job’s tasks and asking whether the candidate genuinely wants that work. Using the EOS filter of understanding the role, wanting it, and having the capacity to do it gives the discussion structure. If a role changes, someone who remains a good fit for the company may need a different position. She wants leaders who continue developing other leaders.

The surprising part of Spencer’s story is that the original goal had become possible before she acted on it. The business could provide more freedom, but she was still working as though it were in its earliest stage. She realized she needed to use the support the company could now afford.

After adding an assistant and a strong operations director, she could step back. She says the company grew further during that period. Her account ties that growth to a change in her role, rather than claiming that taking time off alone produces revenue.

She began protecting complete days off and, by the interview, had taken two six-week sabbaticals in the preceding two years. Maintaining the boundary remained a habit she had to practice. Her husband helped hold her accountable when a quick email threatened to consume personal time. Spencer had seen the cost of constant work in her family life and wanted to avoid recreating the conditions she originally left.

Spencer ends with a standard she applies regardless of how someone else behaves: do the right thing and take the high road. She looks for the same belief when hiring.

That commitment gives her a way to evaluate decisions beyond the next growth opportunity. The people in the company, the work they deliver, and the life she wants outside it remain part of the decision. Her confidence comes from being clearer about those priorities and acting consistently with them.