Chapter 15: Exploring Self Employment and Portfolio Careers
A genuine alternative, not a fallback
Not everyone in transition is looking for another permanent role. Consultancy, freelancing, interim work and portfolio careers, where you combine several part time or project based roles, are all genuine paths, and several major outplacement providers now build them into their programmes as a standalone option rather than treating self employment as a last resort.
What to consider
Be realistic about cash flow, particularly in the first six to twelve months, and understand your tax and employment status obligations, including IR35 considerations if you plan to contract in the UK. Self employment also requires you to market yourself continuously, which is a different skill from job searching and worth developing deliberately rather than assuming it will follow naturally. Consider starting with a small pilot, such as one part time consultancy engagement alongside continued employed search, rather than committing fully before testing the model.
In practice: Helen's portfolio career
After twenty years in corporate operations roles, Helen chose to build a portfolio combining two days a week of interim consultancy with a small non executive advisory role. The transition took longer to establish financially than a single permanent role would have, but gave her a variety and autonomy she had not had in her previous career.
In practice: Graham's tested pilot
Graham, a former IT director, tested self employment cautiously by taking on one short term consultancy project while continuing to apply for permanent roles in parallel. The project went well enough that a second client approached him directly on the strength of the first, and within four months he had a stable enough pipeline to commit to self employment fully, having tested the model before relying on it.
- Committing fully to self employment without any financial runway or pilot period.
- Underestimating the time required to market yourself continuously, separate from delivering the work itself.
- Overlooking tax and employment status obligations until they become urgent.
- Assuming self employment is a lesser path rather than a genuine, deliberate choice.
A note of supportIf part of what draws you towards self employment is a wish to never again feel as exposed to a single employer's decisions as redundancy has made you feel, that is a completely reasonable motivation, and worth naming honestly with your coach as you weigh the practical considerations in this chapter. Whichever path you choose, permanent role, portfolio career or full self employment, your value as a professional does not depend on which one you pick.
- Honestly assess your financial runway if you were to pursue self employment or portfolio work.
- Research the tax and status obligations relevant to your situation before committing.
- Speak to at least one person already working in the model you are considering.
- Consider a small pilot engagement before deciding whether to commit fully.
This programme gives you frameworks and actions. Your coach is where they become genuinely yours. Rather than arriving with answers, consider bringing these open questions into your next session and exploring them together:
- What is genuinely pulling you towards independence: control, safety, freedom, something else?
- What fear sits underneath the caution you feel about this path?