When I started applying to internships in Washington, DC for the first time, I looked up people with the jobs I wanted to have in the future to see where they interned and held entry-level positions. This gave me an idea of where I should apply and also gave me a list of experiences I wanted to have at jobs and internships while in graduate school to start my career in my current industry. The strategy worked in the long run: I was able to secure some of the most competitive jobs in my field and eventually design my ideal job and sell it with a higher salary.
This same strategy can be used for skills and competencies to further advance your career. Paying attention to the skills those around you have as well as investigating skills and competencies on LinkedIn profiles or in job postings can provide an idea of how to make yourself more marketable. This search can also just give you an idea of what you want to learn, what interests you the most. We can often go in a number of directions to advance our career, and leaning into areas in which we are naturally passionate increases the potential to sustain motivation when acquiring new skills.
Wanting to gain additional skills and knowledge is one thing, but identifying the specific skills and determining how to gain them can be less apparent. Prioritizing individualized learning can be even more difficult when you have one job with a specific job description that does not offer room for much creativity.
Using a side hustle, side hustles, or another job can often provide the solution to a lack of creativity at your main job by offering a space where you can grow your skills in a different environment. Jobs, side hustles, and hobbies often have overlapping skills even if they fall within entirely different industries. Using the various spaces in your life to grow skills that create a benefit across multiple environments can multiply your value across the board.
Identifying Skills You Want
To figure out what skill you want to gain, start with what inspires you. If you want to advance in your career, consider what skills you use or could use in your side hustle that would benefit your career progression. This may mean trying new approaches in your side hustle, but side hustles often provide a freer creative space than a workplace with the constraints of time and other people’s priorities.
If you feel inspired to grow your side hustle and feel a bit stagnant, recognize what skills or processes from your day job could benefit your side hustle. Skills can flow in either direction to benefit you!
In my experience, I often start using some technical skills out of necessity in a side hustle and then inevitably notice an application at my day job. This ability to identify both problems and solutions was a huge factor in designing my own job, and I have side hustles to thank for keeping me creative so I can continue to explore innovative solutions at my day job. On the other hand, applying well-established processes from your day job may help you grow a side hustle. For example, your day job likely has processes for onboarding and developing standard operating procedures to guide new employees. Mimicking these processes when you eventually want to expand your side hustle can improve your side hustle’s business processes. There is no right way to cross over skills between a side hustle and a job because developing skills in either space is likely to be beneficial to both!
Experiment with Skills in Low-Stakes Situations
Using your side hustle as a stress-free space to develop skills that you will eventually use in your day job is the most apparent and natural way to skill-share between your obligations. This journey can begin as simply as seeing a job posting for a job you would love to obtain in the future, seeing a skill that you do not yet have, and identifying a potential use for that skill in your side hustle. This gives you time to develop the skill on your own time and potentially launch it at your day job once you get comfortable with it.
This is a more targeted skill generation approach, but skill development may be a lot more authentic as well. Encountering an issue in your side hustle will prompt you to seek a solution. That solution may require you gaining a new skill, and that new skill may be transferable to your day job. Even if you could bring a skill to your workplace immediately, experimenting with it in a side hustle setting can bolster the confidence required to suggest a new approach. Changing processes within workplaces can be difficult, and that extra confidence may be just what you need to introduce an innovation.
Adopting new approaches in a side hustle also has a greater probability of being fun for you. You are more likely to adopt the solution you feel is most enjoyable or efficient rather than adopting a longstanding process that prevailed in your workplace for the past five years. You are more likely to pick a creative approach, one that uses more recent innovations. You also may figure out how to solve a problem with a lower budget than a large company would. We simply approach innovating in our side hustles differently than innovating at work because we have the independence to think for ourselves. Workplaces have a weird way of not allowing the space for creativity until it is absolutely necessary and then awarding creativity that materialized out of nothing. Having a separate creative space sets you up to take advantage of those opportunities.
Using Your Skills to Catapult Your Career Success
Improving skills for the workplace is usually a cumulative process over time. Using skills in various environments maximizes your proficiency and your situational knowledge regarding when to apply certain areas of your expertise.
I am self-taught in Excel and used it for all the elementary reasons folks use Excel in the beginning of my career, but I played in Excel a bit because it was fun and interesting. Then, I started managing billions of dollars in Excel at a job and needed to improve my Excel proficiency rapidly, so I did. With my new above-average Excel skills, I began playing with my own finances using Excel and started habits like tracking my net worth along the way. Using Excel in my personal life and at my job accelerated my learning. Soon I was using Excel to run an Etsy business, created an Excel-based exercise competition for my rugby team at the beginning of the COVID-19 pandemic, and continued to grow my skills at my day job. Somewhere along the way, I became an expert in Excel who now teaches tutorials on everything from basic pivot tables and formulas to writing macros to expedite simple tasks.
I cannot imagine my Excel expertise developing comprehensively without repeated choices to use the skill in many different areas of my life. Exposing a skill to various contexts facilitated rapid knowledge growth. Each new area of application built that skill to a new level, and each new creative project required all the previous contexts so that I had the experience to address the latest challenge.
This is why using a skill in the context of multiple jobs, side hustles, and/or hobbies is so valuable. You will encounter more diverse scenarios and grow your expertise to levels that would be unlikely, or even impossible, by growing the skill at your job alone. Using a skill beyond the workplace will make you more valuable in the workplace.
Skill development in multiple environments also has the potential to grow your career much faster than expected, if you can pinpoint the similarities between different jobs, side hustles, and hobbies. In the summer of 2022, I became my day job’s content manager for our team’s website. This introduction prompted my thinking about the user experience and the best ways to organize content to make it easily accessible but informative and complete. I was far from an expert, having just dipped my toes into content and knowledge management. In the fall of 2022, we learned Patrick was going to leave the Department of Justice, and I began creating a plan for the content of his website. By December 2022, I built this entire website, expanding my knowledge base by a greater margin than I would have in years as a content manager at my day job. This gave me the confidence to overhaul my team’s website in summer 2023, continue my development at work, and actually include knowledge management as an area of expertise. Weaving experiences from a day job and a side hustle (for me) compounded my learning, raised my salary, and made me an expert in a fraction of the time it would have taken working in any one environment.
All the skills you develop outside of your day job transfer. Using them in diverse experiences will refine your expertise rapidly. This includes soft skills, not just technical ones. Working as a teacher has helped me lead tutorials on displaying data in Excel, and it also helped me be a better rugby coach. All of our experiences serve as tools to improve our competency in the future. The more skills you accumulate, the more opportunities you have to grow your career, and the more options you have when exploring how you want to generate the income you need.
Using Your Career to Improve Your Side Hustle
Your side hustle can offer a safer setting to play with innovative ideas for your day job, but your day job can also help grow your side hustle, particularly if you are looking to grow your side hustle into full-time entrepreneurship. Patrick would have been a fantastic tax lawyer running a tax and financial services business immediately after finishing law school, but his experiences at his prior day jobs made him better. Litigating the most complex tax cases in the country, often with multinational companies and the wealthiest Americans trying to skirt taxes, provided a more complete understanding of international tax intricacies to help clients around the country and around the world. It is unlikely that he would have worked with clients of that caliber for years, if ever, if he began his career in entrepreneurship, but experience in those cases makes him a more knowledgeable tax attorney.
On a simpler level, established workplaces have some valuable processes to take in a growing side hustle. Hiring practices, task management, scheduling practices, and other simple but necessary processes can be mimicked easily. In the case of Phippen Tax, I provided most of the organizational structure and processes because management consultants tend to work with these processes more than tax attorneys, but anyone can copy a general structure before making it their own.
The credibility and experience from a typical career is a real asset when becoming an entrepreneur. Most new businesses fail. Thinking through a business model, leaning into an area of expertise, and adopting best practices from a number of different places decrease the probability of failure. I cannot imagine Phippen Tax & Financial Services being as successful as it is today without both Patrick and my cumulative skills and competencies gained from our other careers, side hustles, and hobbies. Luckily, we both have a lot of interests, and this business is the perfect culmination of many of those interests and areas of expertise. Finding the intersection of your own interests and areas of expertise will likely lead to a successful business as well, particularly if you take the best pieces of your prior experiences and mold them into your own creative brand.
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