From Job Loss to Entrepreneurship

Episode 285 - You May Not Want Another Job — You May Want Your Own Business

One of the most interesting shifts post-COVID is the increase in the number of professionals choosing small businesses over large institutions. Many are seeking more autonomy, flexible work arrangements, less bureaucracy, quicker decision-making, and the satisfaction of building something tangible. TJ notes that while corporate skills like management and communication are incredibly valuable, small business operations demand flexibility, problem-solving, and comfort with ambiguity.

It’s also true that more professionals today are seeking purposeful careers that allow them to apply their skills in more entrepreneurial environments. As corporate professionals rethink what success means to them, many are finding new energy in small business ventures, whether by starting something of their own or joining a growing company.

In this episode of The Job Hunting Podcast, I interviewed TJ Slattery, founder of Crow's Nest Consulting. With a background that includes founding a brewery and advising small business owners across the U.S., TJ shares a wealth of insights for professionals looking to transition from corporate life to the small business world.

Key Challenges and Misconceptions in Transitioning to Entrepreneurship

TJ introduced the concept of "entrepreneurial hubris," the tendency for new entrepreneurs to overestimate their readiness and underestimate the complexity of running a business. This overconfidence often leads to magical thinking, where step two of a business plan is assumed to naturally follow from step one. Drawing from a humorous South Park reference, TJ highlights the common mistake: "Step one: start business. Step two: ??? Step three: profit." This theme resonated deeply with my observations in career coaching. Many job seekers believe they can navigate entrepreneurship or job hunting without professional help, only to seek assistance months later when they face continued challenges. In our conversation on the podcast, you will notice that we both emphasized the importance of realistic planning, humility, and early investment in expert support.

Entrepreneurs, Here Are Some Actionable Strategies for Exploring Business Ownership

Model Your Business Financials Early: TJ recommends mapping out a one-to-five-year financial plan, including revenue goals, overhead, staffing needs, and potential risks. Understanding fixed and variable costs at the outset helps avoid unexpected losses and enables more informed decision-making.
Avoid Magical Thinking: Rather than assuming success will come naturally, professionals should pressure-test their ideas. TJ encourages finding a trusted advisor who can poke holes in the business plan and provide honest feedback.
Understand Your Strengths and Weaknesses: Introspection is key. New business owners should evaluate which tasks they excel at and which require outsourcing. This could include marketing, accounting, and sales.
Plan for Failure and Disruption: Build a fallback plan in case revenue dips or suppliers fail. TJ advises creating a list of "existential dreads"—worst-case scenarios—and addressing them with contingency plans. This exercise alleviates stress and improves long-term resilience.
Know When to Seek Help: The right time to engage a business advisor is before problems escalate. TJ sees better outcomes with clients who reach out proactively rather than after being overwhelmed.

Job Seekers, Here is What It Takes to Work in a Small Business Environment

Expect Less Structure: Unlike corporates with onboarding programs and HR policies, many small businesses lack formal systems. Candidates must adapt to ambiguity and self-direct their work.
Be a Swiss Army Knife: Owners often value employees who can wear multiple hats. This may involve helping in unrelated departments or jumping into unfamiliar tasks.
Evaluate the Employer's Clarity: During interviews, ask probing questions about the role and expectations. Small business owners may not fully articulate the job scope, so candidates must seek clarity.
Anticipate a Hands-On Culture: In a small team, roles are fluid. From bartending to bookkeeping, everyone might pitch in to support the business. Flexibility and a willingness to "get your hands dirty" are critical traits.

The Strategic Role of Corporate Professionals in Small Business Growth

We also discussed the growing trend of small businesses hiring experienced professionals to prepare for a sale or a succession plan. These individuals bring structure, financial acumen, and operational excellence to businesses seeking to increase their valuation. For instance:

Finance professionals can implement M&A readiness and help prepare for ISO or B Corp certification.
Operations leaders may standardize processes and create systems that make the business more attractive to buyers.
Professionals with corporate pedigrees are often brought in to lead growth or act as the "number two" to the founder.

These roles often come with long-term incentives and can lead to a significant impact within the business. They provide a unique opportunity to lead strategically while applying years of experience in a more agile, entrepreneurial context.

Future Outlook: Trends in Small Business and Employment

TJ sees continued private equity interest in trades and healthcare, sectors where aging business owners are seeking to retire. This creates opportunities for acquisitions or leadership roles within acquired firms. However, he warns that private equity's short-term focus can sometimes undermine operational sustainability, leaving gaps for professionals who can offer long-term value.

Another trend is the growing need for skilled professionals in trades and personal services. As AI and automation reshape white-collar jobs, hands-on roles, like electricians, plumbers, and therapists, are becoming increasingly vital and valued. This shift underscores the importance of reevaluating career paths and considering overlooked industries with strong growth potential.

Professionals interested in small businesses should begin assessing business models and identifying cost efficiencies now rather than waiting for economic pressures to force tough decisions. Those who act early and plan strategically will be best positioned to thrive.

Conclusion

TJ Slattery's insights provide a grounded and strategic perspective on transitioning from corporate to small business. This episode will be a great listen if you're exploring entrepreneurship or seeking a role within a smaller firm.

The key takeaways include the importance of financial modeling, the pitfalls of entrepreneurial overconfidence, and the strategic advantages experienced professionals can bring to small business environments. As TJ notes, small businesses offer unique opportunities for impact and innovation, provided you’re ready for the reality of less structure and more hands-on work.

This conversation with TJ highlights how corporate professionals can embrace opportunity by stepping into new roles in companies, industries, and sectors they had not considered before. The key is to keep an open mind, seek expert advice, and align your strengths with the needs of growing businesses.