How Can I Work Two Jobs and Be Successful?

July 10, 2023
Posted in Questions
July 10, 2023 Terkel

How Can I Work Two Jobs and Be Successful?

Balancing two jobs is no easy feat, but these ten professionals from various fields have managed to do it successfully. From the strategic planning and mental health balance emphasized by a Founder and CEO, to the job sharing and rotation strategy proposed by a Co-founder, they share their unique insights and strategies that have enabled them to thrive in multiple roles.

  • Plan Strategically and Balance Your Mental Health
  • Consider Job Compatibility
  • Stick to Strict Scheduling
  • Consider Block Scheduling
  • Keep a Strong Sense of Commitment
  • Fuel Your Endurance with Clear Goals
  • Combine Discipline, Prioritization, and Self-Care
  • Align Job Timelines
  • Prioritize Organizational Skills and Work-Life Balance
  • Create a Job Sharing and Rotation Strategy

Plan Strategically and Balance Your Mental Health

Successfully managing two jobs for two years, one as a full-time healthcare investments professional and the other as building my technology startup, Eatearnity, required strategic planning and determination. Expertise in my primary job allowed me to efficiently deliver results within working hours, creating room to focus on my startup.

Managing two jobs involves embracing hard work. With additional responsibilities, time management and reducing distractions become crucial. Also, it’s important to adjust expectations. When I started my side hustle, I was less focused on promotions at my primary job, as juggling two demanding roles would have stretched me thin.

Despite the workload, mental health shouldn’t be compromised. In my routine, weekends were strictly for relaxation, and physical activities were maintained. Successfully juggling two jobs is demanding, but with a balanced approach, it’s doable.

Rafael Sarim ÖzdemirRafael Sarim Özdemir
Founder and CEO, Zendog Labs

Consider Job Compatibility

There were a few tips I adopted in order to successfully work two jobs back in the day and be successful today. One being time management.

Effective time management is crucial when balancing multiple jobs. Create a schedule that allocates specific time slots for each job and prioritize tasks accordingly. Use productivity techniques such as setting deadlines, creating to-do lists, and minimizing distractions to make the most of your time.

I also assessed job compatibility. It’s essential to evaluate the compatibility of the two jobs. If possible, choose jobs that have flexible schedules or allow remote work, making it easier to coordinate between them. Consider whether the roles complement each other or if there are potential conflicts in terms of work hours or job responsibilities.

Successfully handling two jobs requires careful planning, effective communication, and self-discipline. It’s crucial to assess your capabilities and commitments before taking on multiple roles and jobs.

Joe LiJoe Li
Managing Director, CheckYa

Stick to Strict Scheduling

I’ve found that maintaining a strict schedule and sticking to it was crucial in balancing my responsibilities from both jobs.

I also ensured that each of my employers was aware of my circumstances and was flexible with my work hours, which prevented any scheduling conflicts.

Prioritizing tasks based on urgency and importance also helped me stay organized and reduce stress. It allowed me to focus on what needed to be done first and avoid feeling overwhelmed with multiple tasks.

Self-care was another key element. Ensuring I had enough rest and downtime prevented burnout and kept me energized for both jobs.

Michael SenaMichael Sena
Founder and CEO, SENACEA

Consider Block Scheduling

Weaving in and out of two different schedules is not a good way to work. Block scheduling has always been a key part of my multi-job strategy. This is something I learned from years in client services when providing undivided attention to customers during specific hours is much better than 15-30 minute increments all over the place.

Trevor EwenTrevor Ewen
COO, QBench

Keep a Strong Sense of Commitment

Successfully working two jobs requires careful planning, efficient time management, and a strong sense of commitment. To be successful in juggling multiple roles, I relied on a few key strategies.

First, I prioritize my tasks and responsibilities, ensuring that I focus on the most critical and time-sensitive aspects of each job. By setting clear priorities and managing my time effectively, I was able to allocate sufficient attention and effort to both positions.

Secondly, I established open and honest communication with both employers, ensuring they were aware of my situation and commitments. This allowed for flexibility in scheduling and understanding when it came to potential conflicts. Clear communication also helped to manage expectations and establish realistic goals and deadlines.

Additionally, I leveraged technology and productivity tools to streamline my workflow and maximize efficiency. Utilizing project management software, communication platforms, and task management tools was beneficial.

Sai Blackbyrn
Sai Blackbyrn, CEO, Coach Foundation

Fuel Your Endurance with Clear Goals

I worked two jobs for 10 years after graduating college, and I did it successfully because I knew the situation was only temporary and for a good cause—to pay off my student loans so that one day I could work only one job in my chosen field. I am able to do that today as a team lead for a digital media company providing compelling insurance content to consumers.

I was fortunate to find a full-time job in my major when I graduated, but my field was not a well-paid one, especially just starting out and working my way up.

Having a full-time job in my field satisfied me professionally, which enabled me to endure working an additional part-time job to pay my student loan debt. And when I made my last student loan payment, I resigned from my part-time job and hosted a huge celebration with all of the friends I had made from both jobs.

Michelle RobbinsMichelle Robbins
Licensed Insurance Agent,

Combine Discipline, Prioritization, and Self-Care

Successfully working two jobs requires effective time management, discipline, and prioritization. To make it work, plan your schedule with clear timetables for each job, while also allocating time for rest and personal obligations.

Set boundaries and communicate your availability to both employers, avoiding over-commitment. Take care of your physical and mental health by getting enough sleep, eating well, and exercising, while also making time for relaxation.

Stay organized using calendars and reminders, and seek support from friends, family, or colleagues when needed. Regularly assess your workload and make adjustments to maintain balance.

Dennis ConsorteDennis Consorte
Digital Marketing and Leadership Consultant for Startups, Snackable Solutions

Align Job Timelines

Reflecting on my experience of successfully managing two jobs, I attribute much of that accomplishment to aligning job timelines. This technique involves ensuring that the busy periods or peak times at each of my jobs do not coincide. I carefully chose two roles with distinct peak seasons or busy timelines. For instance, if one job had high-demand periods at the end of each quarter, I made sure the other job had a less intense workload during that same time.

By doing this, I ensured that when one job was demanding more of my time and energy, I could afford to give it because my commitments at the other job were relatively less. This helped me to meet the expectations at both workplaces without overstretching myself or compromising on the quality of my work.

Will GillWill Gill
Event Entertainer, DJ Will Gill

Prioritize Organizational Skills and Work-Life Balance

Successfully working two jobs requires careful organization and efficient time management. To stay organized, it is crucial to prioritize tasks and set clear goals. I recommend creating a schedule that allocates specific time slots for each job and adhering to it strictly. Utilizing digital tools such as project management software can be immensely helpful in keeping track of tasks, deadlines, and progress.

Establishing effective communication channels with colleagues and clients is essential. Regularly updating them on progress and addressing any queries promptly fosters trust and maintains a smooth workflow.

Maintaining a healthy work-life balance is vital to sustaining productivity. Allocating time for rest, exercise, and leisure activities rejuvenates the mind and enhances focus, leading to increased efficiency in both jobs.

Lukasz ZeleznyLukasz Zelezny
SEO Consultant, SEO Consultant London

Create a Job Sharing and Rotation Strategy

In order to successfully work two jobs, considering job sharing or job rotation opportunities can be a unique approach. Collaborating with someone who has a similar workload and skill set allows for reduced hours while maintaining productivity.

For example, two part-time employees with complementary schedules can alternate shifts, ensuring coverage and maintaining a work-life balance. This approach offers a flexible solution that maximizes efficiency and job satisfaction. Open communication and clear agreements are crucial in implementing this strategy.

Yoana WongYoana Wong
Co-founder, Secret Florists

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